FEDERAL UNIVERSITY OF TECHNOLOGY MINNA,

MINNA, NIGER STATE, NIGERIA

FUTMINNA e-LEARNING

SCHOOL OF PHYSICAL SCIENCES

COURSE TITLE
ORGANIC CHEMISTRY I

COURSE CODE
CHM 121

COURSE UNIT: 3

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 Course Coordinator
L. A. FADIPE (Ph.D.)
Department of Chemistry
Federal University of Technology, Minna,
Niger State, Nigeria

COURSE DEVELOPMENT TEAM

Subject Matter Experts L. A. Fadipe (Ph.D.)

J. O. Tijani (Ph.D.)
E. Y. Shaba (Ph.D.)
A. ANDREW
A. M. SALIHU
Federal University of Technology, Minna,
Nigeria

L. A. Fadipe (Ph.D.)
Course Coordinator Department of Chemistry
FUT Minna, Nigeria

A. Andrew
Instructional Designers A.M. Salihu
Department of Chemistry,
Federal University of Technology, Minna,
Nigeria

ODL Experts Amosa Isiaka GAMBARI (Ph.D.)

Language Editors

Dean of School Prof. J. Yisa

School of Physical Sciences

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CHM 121 STUDY GUIDE

INTRODUCTION
CHM 121 Organic Chemistry I is a 3- credit unit course for students studying towards

acquiring a Bachelor of Technology in any field. The course is divided into 7 modules and 25

study units. It will first introduce the brief historical development of organic chemistry and

importance of the compounds as well as the Characterizations techniques of Organic

Compounds. Thereafter, bonding in organic compounds, chemistry of functional groups

(Alkane, Alkenes, Alkynes and Aromatic Hydrocarbons), non-aromatic hydrocarbons (alkyl

halides, alcohols, carbonyl compounds and carboxylic acids, and as well as its derivatives)

are discussed. Also, the concept of Reaction Mechanism, Kinetics and Stereochemistry will

be introduced. Finally, the student is introduced to the chemistry of selected metals and non-

metals, and the transition metals.

The course guide therefore gives you an overview of what CHM 121 is all about, the
textbooks and other materials to be referenced, what you expect to know in each unit, and
how to work through the course material.

RECOMMENDED STUDY TIME

This course is a 3-credit unit course having 25 study units. You are therefore enjoined to
spend at least 3 hours in studying the content of each study unit.

WHAT YOU ARE ABOUT TO LEARN IN THIS COURSE

The overall aim of this course, CHM 121 is to introduce you to basic concepts of Organic
Chemistry I. At the end of this course you should be able to:
i. Describe the brief history of development of organic chemistry and its importance
ii. Explain the Characterizations techniques of Organic Compounds
iii. Describe the bonding in organic compounds
iv. Explain the chemistry of Alkane, Alkenes, Alkynes, and Aromatic Hydrocarbons

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 v. Identify non-aromatic hydrocarbons and their reactions
vi. Describe the concept of Reaction Mechanism, Kinetics and Stereochemistry
vii. Describe metals, non-metals and transition metals

COURSE AIMS
This course aims to introduce students to the basic concepts of Organic Chemistry I. It is
expected that the knowledge will enable the reader to effectively use the knowledge of
Organic Chemistry in his/her profession.

COURSE OBJECTIVES
It is important to note that each unit has specific objectives. Students should study them
carefully before proceeding to subsequent units. Therefore, it may be useful to refer to these
objectives in the course of your study of the unit to assess your progress. You should always
look at the unit objectives after completing a unit. In this way, you can be sure that you have
done what is required of you by the end of the unit.

However, below are overall objectives of this course. On completing this course, you should
be able to:
(i). define organic chemistry
(ii). account for the history of organic chemistry and synthesis of Urea
(iii). list and explain different methods of isolating organic compounds
(iv). list and explain different methods of purification of isolated organic compound
(v). explain both qualitative and quantitative techniques for characterizing organic
compounds
(vi). list the steps involved in the identification of organic compounds
(vii). identify fullerenes as the fourth allotrope of carbon
(viii). describe the forms and shape fullerenes (C60)
(ix). mention the properties of fullerenes
(x). list the applications/uses of fullerenes
(xi). describe covalent bonds
(xii). define bond length and bond strength
(xiii). differentiate between sigma bond and pi bonds
(xiv). explain the formation of sp3, sp2 and sp orbitals
(xv). identify the hybridization present in an organic compound
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 state the characteristics of all hybridised orbitals
(xvi). give a general classification of organic compounds
(xvii). explain the criteria for the classification of organic compounds
(xviii). Identify different types of carbon present in an organic compound
(xix). draw structural formula
(xx). give a condensed form of any compound
(xxi). list for function group in a compound
(xxii). define isomerism, Homologous series, and functional group
(xxiii). identify the functional group present in a compound.
(xxiv). identify the longest chain of an organic compound.
(xxv). name any organic compound.
(xxvi). list the rules for naming any organic compound.
(xxvii). mention the sources of Alkanes hydrocarbon
(xxviii). give an IUPAC nomenclature of any saturated hydrocarbon
(xxix). state the physical properties of Alkanes homologous group.
(xxx). mention the reactions of Alkanes
(xxxi). describe the preparation of Alkanes
(xxxii). name most alkene compound
(xxxiii). describe the preparation of Alkenes
(xxxiv). list the physical properties of Alkenes
(xxxv). describe some important reactions of Alkenes
(xxxvi). names of alkyne compounds
(xxxvii). describe the preparations of Alkynes
(xxxviii). list and describe the reactions of Alkynes
(xxxix). define aromaticity
(xl). give examples of aromatic compound
(xli). give the names of some aromatic compound
(xlii). describe some reactions of aromatic compound
(xliii). state some properties of some member of the group
(xliv). give the correct names of halo-hydrocarbon
(xlv). classify any halo-hydrocarbon as primary, secondary or tertiary halo-hydrocarbon
(xlvi). describe at least one preparation method of halo-alkane
(xlvii). discuss the reactions of halo-hydrocarbons
(xlviii). give the classification of Alkonols
(xlix). give the IUPAC names of Alkanols
(l). describe the preparation of primary and secondary Alkanols
(li). describe the chemical reactions of alkanols.
(lii). differentiate between aldehydes and ketones
(liii). describe their preparations
(liv). give their iupac nomenclature

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 (lv). discuss their chemical properties
(lvi). name any carboxylic compounds
(lvii). describe the preparation of simply carboxylic compound
(lviii). discuss the chemical properties of carboxylic groups
(lix). identify ether, ester, amine and amide
(lx). give the iupac names of any compound of the above mentioned groups
(lxi). list the properties of each group mentioned above
(lxii). define reaction mechanism and kinetics
(lxiii). differentiate between a first and second order reaction
(lxiv). define stereochemistry and stereoisomerism
(lxv). identify a stereogenic center(carbon)
(lxvi). define metals, non-metals and transition metals
(lxvii). list and explain the properties of metals in IA, IIA and IVA groups
(lxviii). list and explain the properties of non-metal elements in IA, IIA and IVA groups
(lxix). list and explain the properties of transition metals

WORKING THROUGH THIS COURSE

In order to have a thorough understanding of the course units, you will need to read and
understand the contents, practice the steps by designing and implementing a mini system for
your department, and be committed to learning and implementing your knowledge.
This course is designed to cover approximately sixteen weeks, and it will require your
devoted attention. You should do the exercises in the Tutor-Marked Assignments and submit
to your tutors.

COURSE MATERIALS
The major components of the course are:
1. Course Guide
2. Study Units
3. Text Books
4. Assignment File
5. Presentation Schedule

STUDY UNITS
There are 25 study units and 7 Modules in this course. They are:
MODULE 1: History And Importance Of Organic Chemistry

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UNIT 1: Vital Force Theory And Laboratory Synthesis Of Urea

UNIT 2: Fullerenes (Fourth Allotrope Of Carbon)

UNIT 3: Uses (Nanotubes, Nanostructures)

MODULE 2: Characterisation of Organic Compounds

UNIT 4: Isolation And Purification Of Organic Compounds

UNIT 5: Determination Of Structures Of Organic Compounds (Qualitative And Quantitative)

Analysis In Organic Chemistry

UNIT 6: Classification Of Organic Compounds And Functional Groups

UNIT 7: Structural Formula And Nomenclature
MODULE 3: Electronic Theory In Organic Chemistry

UNIT 8: Bonding In Organic Compounds

UNIT 9: Hybridization
MODULE 4: Chemistry Of Functional Groups
UNIT 10: Alkanes
UNIT 11: Alkenes
UNIT 12: Alkynes
UNIT 13: Aromatic Hydrocarbons
MODULE 5: Introduction To Non-Hydrocarbons

UNIT 14: Alkyl Halides

UNIT 15: Alcohols

UNIT 16: Carbonyl Compounds

UNIT 17: Carboxylic Acids And

UNIT 18: Derivatives Of Carboxylic Acids And Others

MODULE 6: Introduction to Reaction Mechanism, Kinetics and Stereochemistry

UNIT 19: Reaction Mechanism

UNIT 20: Reaction Kinetics

UNIT 21: Stereochemistry

MODULE 7: The Chemistry Of Selected Metals And Non-Metals

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UNIT 22: Chemistry Of Selected Metals

UNIT 23: Chemistry Of Selected Non-Metals

UNIT 24: Comparative Chemistry Of Group Ia, Iia And Iva Elements

UNIT 25: Introduction To Transition Metal Chemistry

RECOMMENDED TEXTS
The following texts and Internet resource links will be of enormous benefit to you in learning
this course:

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.
Strohfeldt , K. A. 2015. Essential Inorganic Chemistry for students in Pharmaceutical
Sciences and Medicinal Chemistry. Library of congress cataloging - in- publication data.
ISBN 978-0-470-66558-9

ASSIGNMENT FILE
The assignment file will be given to you in due course. In this file, you will find all the details
of the work you must submit to your tutor for marking. The marks you obtain for these
assignments will count towards the final mark for the course. Altogether, there are tutor
marked assignments for this course.

PRESENTATION SCHEDULE
The presentation schedule included in this course guide provides you with important dates for
completion of each tutor marked assignment. You should therefore endeavour to meet the
deadlines.

ASSESSMENT

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There are two aspects to the assessment of this course. First, there are tutor marked
assignments; and second, the written examination. Therefore, you are expected to take note of
the facts, information and problem solving gathered during the course. The tutor marked
assignments must be submitted to your tutor for formal assessment, in accordance to the
deadline given. The work submitted will count for 40% of your total course mark.
At the end of the course, you will need to sit for a final written examination. This
examination will account for 60% of your total score. You will be required to submit some
assignments by uploading them to CHM 121 page on the u-learn portal.

TUTOR-MARKED ASSIGNMENT (TMA)

There are TMAs in this course. You need to submit all the TMAs. The best 10 will therefore
be counted. When you have completed each assignment, send them to your tutor as soon as
possible and make certain that it gets to your tutor on or before the stipulated deadline. If for
any reason you cannot complete your assignment on time, contact your tutor before the
assignment is due to discuss the possibility of extension. Extension will not be granted after
the deadline, unless on extraordinary cases.

FINAL EXAMINATION AND GRADING

The final examination for CHM 121 will last for a period of 3 hours and has a value of 60%
of the total course grade. The examination will consist of questions which reflect the self-
assessment questions and tutor marked assignments that you have previously encountered.
Furthermore, all areas of the course will be examined. It would be better to use the time
between finishing the last unit and sitting for the examination, to revise the entire course. You
might find it useful to review your TMAs and comment on them before the examination. The
final examination covers information from all parts of the course.

PRACTICAL STRATEGIES FOR WORKING THROUGH THIS COURSE

1. Read the course guide thoroughly
2. Organize a study schedule. Refer to the course overview for more details. Note the
time you are expected to spend on each unit and how the assignment relates to the
units. Important details, e.g. details of your tutorials and the date of the first day of the
semester are available. You need to gather together all these information in one place

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 such as a diary, a wall chart calendar or an organizer. Whatever method you choose,
you should decide on and write in your own dates for working on each unit.
3. Once you have created your own study schedule, do everything you can to stick to it.
The major reason that students fail is that they get behind with their course works. If
you get into difficulties with your schedule, please let your tutor know before it is too
late for help.
4. Turn to Unit 1 and read the introduction and the learning outcomes for the unit.
5. Assemble the study materials. Information about what you need for a unit is given in
the table of content at the beginning of each unit. You will almost always need both
the study unit you are working on and one of the materials recommended for further
readings, on your desk at the same time.
6. Work through the unit, the content of the unit itself has been arranged to provide a
sequence for you to follow. As you work through the unit, you will be encouraged to
read from your set books
7. Keep in mind that you will learn a lot by doing all your assignments carefully. They
have been designed to help you meet the objectives of the course and will help you
pass the examination.
8. Review the objectives of each study unit to confirm that you have achieved them.
If you are not certain about any of the objectives, review the study material and
consult your tutor.
9. When you are confident that you have achieved a unit’s objectives, you can start on
the next unit. Proceed unit by unit through the course and try to pace your study so
that you can keep yourself on schedule.
10. When you have submitted an assignment to your tutor for marking, do not wait for its
return before starting on the next unit. Keep to your schedule. When the assignment is
returned, pay particular attention to your tutor’s comments, both on the tutor marked
assignment form and also written on the assignment. Consult you tutor as soon as
possible if you have any questions or problems.
11. After completing the last unit, review the course and prepare yourself for the final
examination. Check that you have achieved the unit objectives (listed at the beginning
of each unit) and the course objectives (listed in this course guide).

TUTORS AND TUTORIALS

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There are few hours of tutorial provided in support of this course. You will be notified of the
dates, time and location together with the name and phone number of your tutor as soon as
you are allocated a tutorial group. Your tutor will mark and comment on your assignments,
keep a close watch on your progress and on any difficulties you might encounter and provide
assistance to you during the course. You must mail your tutor marked assignment to your
tutor well before the due date. At least two working days are required for this purpose. They
will be marked by your tutor and returned to you as soon as possible.

Do not hesitate to contact your tutor by telephone, e-mail or discussion board if you need
help. The following might be circumstances in which you would find help necessary: contact
your tutor if:
• You do not understand any part of the study units or the assigned readings.
• You have difficulty with the self-test or exercise.
• You have questions or problems with an assignment, with your tutor’s comments on an
assignment or with the grading of an assignment.

You should endeavour to attend the tutorials. This is the only opportunity to have face to face
contact with your tutor and ask questions which are answered instantly. You can raise any
problem encountered in the course of your study. To gain the maximum benefit from the
course tutorials, have some questions handy before attending them. You will learn a lot from
participating actively in discussions.

GOODLUCK!

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 TABLE OF CONTENTS
MODULE 1: History And Importance Of Organic Chemistry

UNIT 1: Historical survey of the development and importance of organic Chemistry

UNIT 2: Fullerenes (Fourth Allotrope of Carbon)

MODULE 2: Characterisation of Organic Compounds

Unit 1: Isolation And Purification Of Organic Compounds

Unit2: Determination Of Structures Of Organic Compounds Including Qualitative And

Quantitative Analysis In Organic Chemistry

Unit 3: Classification Of Organic Compounds And Functional Groups

Unit 4: Structural Formula And Nomenclature
MODULE 3: Electronic Theory In Organic Chemistry

Unit 1: Bonding In Organic Compounds

Unit 2: Hybridization
MODULE 4: Chemistry of Functional Groups
Unit 1: Alkane
Unit 2: Alkenes
Unit 3: Alkynes
Unit 4: Aromatic Hydrocarbons
MODULE 5: Introduction To Non-Hydrocarbons

Unit 1: Alkyl Halides

Unit 2: Alcohols

Unit 3: Carbonyl Compounds

Unit 4: Carboxylic Acids

Unit 5: Derivatives Of Carboxylic Acids And Others

MODULE 6: Introduction to Reaction Mechanism, Kinetics and Stereochemistry

Unit 1: Reaction Mechanism

Unit 2: Reaction Kinetics

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Unit 3: Stereochemistry

MODULE 7: The Chemistry Of Selected Metals And Non-Metals

Unit 1: Chemistry Of Selected Metals

Unit 2: Chemistry Of Selected Non-Metals

Unit 3: Comparative Chemistry Of Group IA, IIA And IVA Elements

Unit 4: Introduction To Transition Metal Chemistry

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MODULE 1: History and Importance of Organic Chemistry
Unit 1: Historical survey of the development and importance of organic Chemistry
1.0 Introduction……………………………………………….………….…
2.0 Learning Outcomes ……………………………………………………
3.0 Learning Contents………………………………………………………
3.1 Historical survey and development of organic chemistry………………
3.2 Importance of organic chemistry………………………………………21
4.0 Conclusion …………………………………………………………………24
5.0 Summary………………………………………………………………24
6.0 Tutor-Marked Assignments …………………………………………...25
7.0 Recommended Books………………………………………………….25
Unit 2: Fullerenes (C60)---------------------------------------------26
1.0 Introduction……………………………………………….………….…26
2.0 Learning Outcomes ……………………………………………………27
3.0 Learning Contents………………………………………………………27
3.1 Discovery of fullerenes……………………..…………………………..27
3.2 physical and chemical properties of fullerenes………………….…….28
3.3 applications/uses of fullerenes (nanotubes, nanowares)………………..28
4.0 Conclusion ………………………………………………………………….29
5.0 Summary………………………………………………………………..29
6.0 Tutor-Marked Assignments ……………………………………………30
7.0 Recommended Books…………………………………………………..30
MODULE 2: ISOLATION, PURIFICATION AND IDENTIFICATION OF ORGANIC COMPOUNDS
Unit 1: ISOLATION AND IDENTIFICATION OF ORGANIC COMPOUNDS ...
1.0 Introduction……………………………………………………..…………
2.0 Learning Outcomes…………………………………………….………….
3.0 Learning Contents…………………………………………………………
3.1 Isolation of Organic Compounds……………………………………
3.2 Identification of Organic Compounds…………………………
4.0 Conclusion……………………………………………………….…
5.0 Summary……………………………………………………………
6.0 Tutor Assessment Exercise…………………………………………
7.0 Recommended Books………………………………………………
Unit 2: CHARACTERIZATION OF ORGANIC COMPOUNDS..………….
1.0 Introduction………………………………………………………..…………
2.0 Learning Outcomes……………………………………………….………….
3.0 Learning Contents……………………………………………..……………

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3.1 Qualitative test for Organic compounds………………………………
3.2 Quantitative test for Organic Compounds……………………….
4.0 Conclusion………………………………………………….…………
5.0 Summary……………………………………………………..
6.0 Tutor Assessment Exercise………………………………………
7.0 Recommended Books………………………………………..………

MODULE 3: ELECTRONIC THEORIES IN ORGANIC CHEMISTRY

Unit 1: BONDING IN ORGINC COMPOUNDS………………………………………...
1.0 Introduction…………………………………………………………….………….
2.0 Learning Outcomes……………………………………………………….………..
3.0 Learning Contents………………………………………………..……………….
3.1 Atomic Orbital theory…………………………………………………………..…
3.2 Molecular Orbital theory………………………………………………
3.3 Bond Order and magnetic property………………………………………………..
3.4 Covalent Bond…………………………………………………………..…………
3.2 Bond Length and Bond Strength………………………………………………
3.3 Bond Polarity and Dipole Moment………………………………………………..

4.0 Conclusion………………………………………………………………………..
5.0 Summary…………………………………………………………………………
6.0 Tutor-Marked Assignments………………………………………………………
7.0 Recommended Books……………………………………………………………
Unit 2: HYBRIDIZATION………………………………………………………………
1.0 Introduction ………………………………………………………………...……
2.0 Learning Outcomes…………………………………………………………..
3.0 Learning Contents……………………………….……………………………
3.4 Hybridization (Sp3, sp2 and sp hybridization) …………………………….
4.0 Conclusion…………………………………………………………………….
5.0 Summary……………………………………………………..………………..
6.0 Tutor Assessment Exercise……………………………………………………
7.0 Recommended Books…………………………………………………………
MODULE 4: CLASSIFICATION OF ORGANIC COMPOUNDS AND FUNCTIONAL
GROUPS……....
Unit 1: Hydrocarbons and Non Hydrocarbons
1.0 Introduction………………………………………………………………………

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2.0 Learning Outcomes……………………………………..………………………
3.0 Learning Contents………………………………………………………………
3.1 General Classification of Organic Compounds………………………...
3.2 Functional Groups………………………………………………………
3.3 Homologous Series…………………………………………………..…
4.0 Conclusion…………………………………………………………………
5.0 Summary………………………………………………………….………
6.0 Tutor Assessment Exercise…………………………………………….....
7.0 Recommended Books………………………………………………………
Unit 2: STRUCTURAL FORMULA AND NOMENCLATURE……………………
1.0 Introduction…………………………………………………………………
2.0 Learning Outcomes……………………………………………....
3.0 Learning Contents……………………………………………………
3.1 The Structural Theory of Organic Chemistry………………..
3.2 Isomerism……………………………………………..
3.3 IUPAC Nomenclature of Organic Compounds………………
4.0 Conclusion……………………………………………………
5.0 Summary……………………………………………………………
6.0 Tutor Assessment Exercise…………………………………………
7.0 Recommended Books………………………………………………
MODULE 5: Chemistry Of Functional Groups ………………………………
Unit 1: ALKANE…………………………………………………….………….
1.0 Introduction ………………………………………………………..
2.0 Learning Outcomes………………………………….…………………
3.0 learning Contents………………………………………………………
3.1 Source Of Alkane…………………………………………………….
3.2 Naming of Alkanes and Cycloalkanes……………………………..
3.3 Preparation of Alkanes…………………………………………….
3.4 Physical and Chemical Properties of Alkanes…………….
4.0 Conclusion………………………………………………………
5.0 Summary………………………………………………………..
6.0 Tutor Assessment Exercise…………………………………………….
7.0 Recommended Books………………………………….………………

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Unit 2: ALKENES……………………………………………………………………44
1.0 Introduction…………………………………………………..…………………45
2.0 Learning Outcomes……………………………………….……………………45
3.0 Learning Contents……………………………………………..………………..45
3.1 Geometric Isomers in Alkenes…………………………………….45
3.2 Nomenclature of Alkenes……………………………………………….……….….46
3.3 Preparation of Alkenes…………………………………..………….……….……46
3.4 Physical Properties of Alkenes……………………………………….48
4.0 Conclusion……………………………………………………………………..…….51
5.0 Summary………………………………………………………………………..…51
6.0 Tutor Assessment Exercise……………………………………………………52
7.0 Recommended Books……………………………………………….…….52

Unit 3: ALKYNES……………………………………………………………………53
1.0 Introduction…………………………………………………….……....54
2.0 Learning Outcomes……………………………………………………54
3.0 Learning Contents…………………………………………………….54
3.1 Nomenclature of Alkyne…………………………………………54
3.2 Preparation……………………………………………….…….55
3.3 Physical Properties And Chemical Reaction……………………..56
4.0 Conclusion…………………………………………………………………………..
Summary………………………………………………………………………………....57
6.0 Tutor Assessment Exercise…………………………………………58
7.0 Recommended Books……………………………………..……….58
Unit 4: AROMATIC HYDROCARBONS…………………………………59
1.0 Introduction……………………………………………………………...59
2.0 Learning Outcomes…………………………………………..…….….. 60
3.0 Learning Contents……………………………………………………………...….60
3.1 Sources Of Aromaticity In Aromatic Hydrocarbon…………………………..60
3.2 Nomenclature Of The Aromatic Group…………………………………………..61
3.3 Preparation Of Aromatic Compounds…………………………………………....63
4.0 Conclusion………………………………………………….......................64
5.0 Summary…………………………………………………………………64
6.0 Tutor-Marked Assignment…………………………………………65
7.0 Recommended Books……………………………………….……….65
MODULE 6: INTRODUCTION TO NON-HYDROCARBONS……………66
Unit 1: HALOHYDROCARBONS ……………………………………………………...67

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1.0 Introduction…………………………………………………….…....68
2.0 Learning Outcomes…………………………………………………....68
3.0 Learning Contents ……………………………………………………68
3.1 Classification of Halohydrocarbons……………………….……..68
3.2 Nomenclature of Halohydrocarbons…………………....69
3.3 Preparation and Reactivity…………………………….70
4.0 Conclusion……………………………………………………………..72
5.0 Summary………………………………………………………….…72
6.0 Tutor Marked Assignment………………………………………… 73
7.0 Recommended Books……………………………………………73

Unit 2: HYDROXYL COMPOUNDS…………………………..74

1.0 Introduction………………………………………….……75
2.0 Learning Outcomes…………………………………………………75
3.0 Learning Contents ………………………………………..……75
3.1 Classification of Alcohols………………………….…………75
3.2 IUPAC Nomenclature of Alcohols………………………….…..76
3.3 Physical and Chemical Properties of Alkanols……………….…….77
4.0 Conclusion…………………………………………………………….81
5.0 Summary………………………………………………………………………81
6.0 Tutor Marked Assignment…………………………………………………….. 81
7.0 Recommended Books………………………………………..82

Unit 3: CARBONYL COMPOUNDS……………………………………………83

1.0 Introduction……………………………………………..……….84
2.0 Learning Outcomes………………………………………………....84
3.0 Learning Contents…………………………………………84
3.1 General Classification…………………………………………………….……….84
3.2 IUPAC Nomenclature………………………………………………….......85
3.3 Preparations……………………………………………………………...............….87
3.4 Physical and Chemical Properties……………………….…………………….88
4.0 Conclusion………………………………………………………………...91
5.0 Summary.............................................................................................…...91
6.0 Tutor Marked Assignment ………………………………………..…….92
7.0 Recommended Books………………………………………………….92
Unit 4: ORGANIC ACIDS……………………………………………….93
1.0 Introduction…………………………………………………….………94

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2.0 Learning Outcomes.................................................................................94
3.0 Learning Contents…………………………………………..…….94
3.1 Nomenclature of Carboxyl Acids……………………………..……….94
3.2. Preparation…………………………………………………………….……….…...95
3.3 Properties of Carboxylic Acid………………………………………….…….96
4.0 Conclusion………………………………………….…………….……97
5.0 Summary…………………………………………………….……97
6.0 Tutor Marked Assignment……………………………………………………….98
7.0 Recommended Books………………………………………………….……98

Unit 5: DERIVATIVE OF CARBOXYLIC ACID AND OTHER…………..…………….99

1.0 Introduction……………………………………………………………….…100
2.0 Learning Outcomes……………………………………………………………100
3.0 learning Contents………………………………………………………………………100
3.1 Ethers…………………………………………………………………………..100
3.2 Ester…………………………………………………………………………….101
3.3 Amines………………………………………………………………………..102
4.0 Conclusion………………………………………………………………………..…….104
5.0 Summary……………………………………………………………………..…………104
6.0 Tutor-Marked Assignment………………………………………..…………….104
7.0 Reference…………………………………………………………………105

MODULE 7: Introduction to Reaction Mechanism, Kinetics and Stereochemistry

Unit 1: Reaction mechanism and kinetics …………..…………….99

1.0 Introduction……………………………………………………………….…100
2.0 Learning Outcomes……………………………………………………………100
3.0 learning Contents………………………………………………………………………100
3.1 Definition and types of order…………………………………………………..100
3.2 molecularity and order of reaction………………………………………….101
3.3 arrow movement in reaction mechanism…………………………………..102
4.0 Conclusion………………………………………………………………………..…….104
5.0 Summary……………………………………………………………………..…………104
6.0 Tutor-Marked Assignment………………………………………..…………….104
7.0 Reference…………………………………………………………………105

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Unit 2: stereochemistry …………..…………….99
1.0 Introduction……………………………………………………………….…100
2.0 Learning Outcomes……………………………………………………………100
3.0 learning Contents………………………………………………………………………100
3.1 Definition of stereochemistry and stereoisomer………………………..100
3.2 stereo genic carbon and condition………………………………….101
4.0 Conclusion………………………………………………………………………..…….104
5.0 Summary……………………………………………………………………..…………104
6.0 Tutor-Marked Assignment………………………………………..…………….104
7.0 Reference…………………………………………………………………105
MODULE 8: The Chemistry of Selected Metals and Non-Metals

Unit 1: Metals and Non-metals …………..…………….99

1.0 Introduction……………………………………………………………….…100
2.0 Learning Outcomes……………………………………………………………100
3.0 Learning Contents………………………………………………………………………100
3.1 Chemistry of selected non-metals and metals of group IA,IIA and IVA elements …..100
3.2 Comparative chemistry of group IA, IIA and IVA elements …
4.0 Conclusion………………………………………………………………………..…….104
5.0 Summary……………………………………………………………………..…………104
6.0 Tutor-Marked Assignment………………………………………..…………….104
7.0 Reference…………………………………………………………………105
Unit 2: Transition metals …………..…………….99
1.0 Introduction……………………………………………………………….…100
2.0 Learning Outcomes……………………………………………………………100
3.0 learning Contents………………………………………………………………………100
3.1 definitions
3.2 properties of transition metals (physical and chemical) and applications……………
4.0 Conclusion………………………………………………………………………..…….104
5.0 Summary……………………………………………………………………..…………104
6.0 Tutor-Marked Assignment………………………………………..…………….104
7.0 Reference…………………………………………………………………105

20
 Module
MODULE 1: History and Importance of Organic Chemistry
1
Unit 1 – Historical survey of the development and importance of organic Chemistry
Unit 2 - Fullerenes (Fourth Allotrope of Carbon)
Unit 3 - Uses as Nanotubes, Nanostructures, Nanochemistry

Unit 1
HISTORICAL SURVEY OF THE DEVELOPMENT OF ORGANIC CHEMISTRY

Contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Vital force theory
3.2 Synthesis of Urea

21
 3.3 Importance of organic Chemistry
4.0 Conclusion
5.0 Summary
6.0 Tutor Assessment Exercise
7.0 Reference

1.0 Introduction

Organic Chemistry is the study of carbon and its compounds. A number of organic
compounds were used in ancient times by the Romans and Egyptians as dyes, medicines and
poisons from natural sources, though at that time their structures were not known.

2.0 Learning Outcomes

At the end of this unit, you should be able to:

1. State the vital force theory and the year
2. Explain the synthesis of Urea
3. List the importance of organic chemistry

3.0 Learning Content

3.1 Vital Force

In 1815, Jons Jacob Berzelius believed in an idea of vitalism (that natural organic compounds
were made by a special vital force and therefore came to the conclusion that organic
compounds could not be made in the laboratory).
The theory states that all organic compounds are produced from living organisms due to the
presence of a vital force. .
Self-Assessment Question(s) (SAQ)
1. Who propounded vital force and in which year?

22
Self-Assessment Answers
Vital force theory was propounded by Jons Jacob Berzelius in 1815

3.2 Synthesis of Urea

The ideology of J.J. Berzelius however crashed when in 1828 urea, found in urine was
synthesized by heating a solution containing potassium isocyanate and ammonium sulphate
during a laboratory experiment by Frdrich Wohler (a student of Berzelius) in 1828.

2KNCO + (NH4)2SO4 → 2NH4NCO + K2SO4

NH4NCO ↔ H2N-CO-NH2
Ammonium Urea
cyanate

Self-Assessment Question(s) (SAQ)

When was urea first synthesize and by who?
Where can urea be found naturally?

Self-Assessment Answers
In 1828 and by Fredrich Wohler
In urine

3.3 Importance of Organic Chemistry

23
Organic reactions form basis for understanding reactions in cell biology, physiology and
biochemistry- a foundation for the study of biomedical sciences.
Organic chemistry models the kind of comprehensive learning required for success in courses
such as medicine, pharmacy, etc
Employment opportunity: the knowledge of organic Chemistry combined with analytical
chemistry is required to work effectively and efficiently Quality control, Food Chemistry,
Molecular biology, Environmental contaminant analysis
The flexibility of carbon make organic compounds to be useful in pesticides formulation,
Electronics, etc

Self-Assessment Question(s) (SAQ)

Mention two areas where the knowledge of organic Chemistry can be applied

Self-Assessment Answers
Pharmaceutical and Food Chemistry

Self-Assessment Question(s) (SAQ)

1. Give the molecular formula of urea

2. ------- form the basis for understanding reactions in --------

Self-Assessment Answer(s)
1. H2N-CO-NH2
2. Organic reactions in cell biology, physiology and biochemistry

4.0. Conclusion

The understanding of the importance of organic chemistry will help you to appreciate nature,
predict the likely reaction around.

24
5.0 Summary

1. The vital force, 1815 by J.J. Berzelius, states that all organic compounds are produced
from living organisms due to the presence of a vital force. .
Covalent bond is the mutual sharing of electrons between two atoms of close
electronegativity
2. The first organic substance to be synthesized in the laboratory from inorganic substance
was urea, by heating a solution containing potassium isocyanate and ammonium sulphate by
Frdrich Wohler in 1828.

6.0. Tutor-Marked Assignment

1. Account for the chemical breakthrough of 1828

2. Write a balanced chemical equation for the synthesis of urea from potassium isocyanate
and ammonium sulphate

7.0. Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.
Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.
Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.
Okwute S.K. And Mann A. 2022. Fundamentals of Chemistry. Ibadan University press

Unit 2: Fullerenes (C60)

1.0 Introduction……………………………………………….………….….3
2.0 Learning Outcomes ……………………………………………………………….………...3
3.0 Learning Contents…………………………………………………………..……………….3
3.1 Discovery of fullerenes……………………..…………….3
3.2 structural, physical and chemical properties of fullerenes………………….……………….4
3.3 applications/uses of fullerenes (nanotubes, nanowares)
4.0 Conclusion …………………………………………………………………..…..…5
5.0 Summary…………………………………………………………………………………....6
6.0 Tutor-Marked Assignments ………………………………………………………………...6
7.0 Recommended Books………………………………………………………………………….6

25
FULLERENES (C60)
Unit 2
Contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Discovery of Fullerenes and its structures
3.2 physical and chemical properties of fullerenes
3.3 applications/uses of fullerenes (nanotubes, nanowares)
Conclusion
5.0 Summary
6.0 Tutor Assessment Exercise
7.0 Reference

1.0 Introduction

26
Carbon exists in allotropic forms. These include the crystalline form (diamond) and as well as
the amorphous carbon. In 1985, a team of scientists: Robert F. Curl, Harold W. Kroto and
Richard E. Smalley in Rice University discovered new allotrope of carbon which was named
after an American architect Buckminster Fuller who design the Geodesic dome. The allotrope
also called Bucky ball or Buckminster ball.

2.0 Learning Outcomes

At the end of this unit, you should be able to:

1. State the year and the scientist that discover fullerenes
2. Describe fullerenes
3. List the physical and chemical properties of fullerenes
4. Describe the synthesis of fullerenes
5. Mention the types of fullerenes
6. Mention the applications of fullerenes

3.0 Learning Content

3.1 Discovery of Fullerenes

Fullerenes (C60) contain pentagonal ring and Hexagonal ring with 60 carbon atoms held
together by covalent bond. It has 20 hexagons and 12 pentagons in which no two pentagons
share a net each carbon atom is connected to exactly three (3) neighbouring atoms. Fullerenes
also exist in various other shapes in which the carbon atom arranged in cage-like structure of
hollow sphere (C60), Ellipsoid (C70) and Tubes (nanotubes). Also the hybridization type in
fullerenes is sp2. The substance is synthesized when a large current is passed between two
graphite electrodes in an inert atmosphere such as helium, gives rise to carbon plasma
reaching the anode and cathode and which cooled instantaneously and leaves behind a sooty
residue from which the Bucky ball can be extracted. Fullerenes exist in two forms (closed
Bucky ball and open-ended cylindrical carbon nanotubes).
Self-Assessment Question(s) (SAQ)
2. What is the bonding type and number of carbons in fullerenes.
3. How many are each and the connection between the pentagon and hexagon in
fullerenes?

27
Self-Assessment Answers
Covalent bond and C60
It has 12 pentagons and 20 hexagons and no two pentagons share a net.

3.2 Properties of Fullerenes

Physical properties
1. The behaviour and structure of fullerenes is temperature dependant. As the temperature is
increased fullerene gets converted into the C70
2. It shows high tensile strength
3. Possess good thermal and electrical conductivity
Chemical properties
1. Fullerene is ferromagnetic
2. They are soluble in soluble in many solvents like CS2, it is the only allotrope known to be
soluble.
3. Fullerenes are stable, but not totally unreactive.
4. It acts as an electron-accepting group and is characterized as an oxidizing agent.
5. In chemical reactions fullerene act as an electrophile
6. A fullerene when doped or crystallized with alkali or alkaline earth metals, it showcases
superconductivity properties

Self-Assessment Question(s) (SAQ)

(a). Mention two physical and chemical properties each of fullerene
(b). Which is the only allotrope of carbon soluble CS2

Self-Assessment Answers
(a).1. It shows high tensile strength 2. Possess good thermal and electrical conductivity
1. Fullerene is ferromagnetic 2. In chemical reactions fullerene act as an electrophile
(b). Fullerene

3.3
[Link]/
bond length is theuses of between
distance Fullerenes
the two(Nanotubes
bonding [Link] Nanowares)
1. The higher is
Fullerene theone
degree of overlapping
of the the shorter
nanomaterials the valuable
that have bond length, and also,inthe
application thestronger
field of
the bond and vice versa.
biomedicine. It possesses exceptional antioxidant capacity which has made it a great
ingredient to be used in sunscreen, skin whitening and antiaging products.
2. Fullerenes are being investigated for their potential use as a drug-delivery system for
cancer, AIDS and other diseases

28
3. It is used as lubricant, ball bearing, etc
4. It is also used as catalyst by attaching it to metals
5. It is also used in the purification of contaminated water from free radicals
6. As an organic photovoltaic (n-type material)
7. Composite to strengthen material
Self-Assessment Question(s) (SAQ)
Give five applications of fullerene

Self-Assessment Answers
1. Used in sunscreen, skin whitening and antiaging products.
3. It is used as lubricant and ball bearing
4. It is also used as catalyst by attaching it to metals
5. It is also used in the purification of contaminated water from free radicals

Self-Assessment Question(s) (SAQ)

1. What is the hybridization type in fullerenes?

2. When, where and who discover fullerenes?
3. list two forms of fullerene

Self-Assessment Answer(s)
1. sp2 hbridized
2. 1985, Rice University and Robert F. Curl, Harold W. Kroto and Richard E.
Smalley
3. Nanotube and Nanoware

4.0. Conclusion

The understanding of the chemistry of fullerene will help you to appreciate its unique roles in
the field of nonochemistry, nanoscience and nanotechnology.

5.0 Summary

1. Fullerene is the fourth allotrope of carbon (C60), discovered in 1985 and named after
Buckminster Fuller.
2. The pentagonal ring and the hexagonal rings are held together by a covalent bond, and
carbon is sp2 hybridized

29
3. Some of the physical and chemical properties of fullerenes includes: high tensile strength,
good thermal and electrical conductivity, and Fullerene is ferromagnetic, a good oxidizing
agent and as an electrophile.
4. Some of the applications of fullerene include: It is used as lubricant, ball bearing, as
catalyst by attaching it to metals, in the purification of contaminated water from free radicals,
in organic photovoltaic (n-type material) and Composite to strengthen material

6.0. Tutor-Marked Assignment

1. Describe the following: fullerene, nanotubes and nanowares.

7.0. Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.
Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.
Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.
Okwute S.K. And Mann A. 2022. Fundamentals of Chemistry. Ibadan University press

30
 MODULE 2
Unit 1
Isolation, Purification and
Identification of Organic
Compounds
1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Isolation of Organic Compounds
3.2 Identification of Organic Compounds
4.0 Conclusion
5.0 Summary
6.0 Tutor Assessment Exercise
7.0 Reference

31
1.0 Introduction

Organic compounds can be obtained from natural sources as well as by synthesis in the
laboratory. Whatever is the source of the organic compound, it is usually obtained in an
impure state, meaning that it occurs with small or large amount of contaminants. On account
of this, the desired products have to be separated or isolated from the reaction system,
purified and tested qualitatively and quantitatively to identify the compound and ascertain
that what has been produced is what was intended.
In this unit, we should look at the various method employed to obtain a pure organic
compound after production.

2.0 Learning Outcomes

At the end of this unit, the student should be able to;

list and explain different methods of isolating organic compounds.
list and explain different methods of purification of isolated organic compound.
list the steps involved in the identification of organic compounds.

3.0 Learning Content

3.1 Isolation of Organic Compounds

Organic compounds must be isolated from their natural reaction environment before any test
can be carried out on then to ascertain their purity. Isolation can be done using any suitable
separation or extraction technique, popular methods used include;

Filtration
Concentration
Crystallization
Solvent extraction
Distillation
Fractional Distillation
Isolation method selected will depend largely on the followings:

1. Nature of the environment of the compound of interest. (i.e. solid, liquid or gaseous.)
2. The chemical reactive of the compound of interest.
3. Physical properties like imflammability, volatility, polarity e.t.c.

32
Isolation and purification can be going simultaneously or side by side by combining or
employing two or more separation method. Once the isolation or extraction and purification
steps are completed, the isolate is tested for its purity.

Characteristics of Purity
The following physical properties are used to test the purity of organic compounds;
1. Melting point for solids
2. Boiling point for liquid
3. Angle of rotation
4. Odour, solubility and colour, can be used too.

A compound is adjusted pure when the numeric values of its physical properties remain
constant on further purification.

Self-Assessment Question(s) (SAQ)

What are some of the methods used to isolate organic compounds from their natural
reaction environment?

Self-Assessment Answers

Filtration, Concentration, Crystallization, Solvent extraction, Distillation, Fractional and

Distillation.

3.2 Identification of Organic Compounds

The test for purity can only serve for known compound for the purpose of clarity, proper
identification is necessary new, and/or unknown isolated compound.

For proper identification, the following steps are employed;

1 – Qualitative analysis of the isolate or new compound: This help to determine the
constituent elements of the compound.

2 – Quantitative analysis: This helps to determine the amount of the different element
identified are present. This can help reveal the percentage quantity, the percentage
composition and the empirical formulae, for example: a compound X was found to have the
following by mass: C = 52.2%, H = 13.0%, 0.023g of X occupied a volume of 11.2cm3 at
STP.

33
3 – Functional group determination using chemical reactions that are characteristic of
different functional group and/or by spectroscopic method. Functional group will be
discussed in a later unit.
Deduce the molar formula of X

4.0 Conclusion

The primary aim of any organic synthesis is to produce a compound that is distinct properties.
In the presence of unwanted side products. Such compound must be isolated, purify and
tested. That is the importance of this unit.

5.0 Summary

1. Isolation is the extraction of a targeted compound from its present environment using
suitable separation method.
2. Purity test are carried out to ascertain the purity of the compound isolated.
3. Organic compounds are identified by the analysis of elements present and the reaction
of the functional group present.

6.0 Tutor Marked Assessment

1. State two steps used in the identification of organic compounds?

2. Give one importance of measuring the physical properties of organic compounds?

7.0 Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

34
 Unit 3
Classification of Organic
Compounds and Functional
Groups
Contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 General Classification Of Organic Compounds
3.2 Functional Groups
3.3 Homologous Series
4.0 Conclusion
5.0 Summary
6.0 Tutor Assessment Exercise
7.0 Reference

1.0 Introduction

35
Carbon’s ability to form as many as four strong bonds to other elements including carbon
atom provides the necessary versatility of the structure. In this unit, you will study the
different ways in which organic compounds are group and organized.

2.0 Learning Outcomes

At the end of this unit, the student should be able to;

1. Give a general classification of organic compounds
2. Explain the criteria for the classification of organic compounds.
3. Identify different types of carbon present in an organic compound.

3.0 Learning Content

3.1 General Classification of Organic Compounds

Organic compounds have different classification depending on the criteria being used.
However, there is the general classification which combined their functional groups and
chemical composition as shown below.

Organic Compound

Hydrocarbon Non-Hydrocarbon

Alkanol Carbonyl Amides Alkanoic

acid
Aliphatic Aromatic

Alkane Alkene Alkyne

Organic compound are generally grouped into two that is Hydrocarbon and Non-
Hydrocarbon. The hydrocarbons are those organic compounds which are composed mainly of
carbon and hydrogen; examples are CH4, C2H4, C2H2, e.t.c while the non – hydrocarbon are

36
those ones that have the presence of other elements apart from carbon and hydrogen. These
include the alcohols, organic acid, carbonyl groups.

The hydrocarbons are further grouped in two based on the chain/structural arrangement.
These groups are:

Aliphatics which have the straight chain with open ends and the Aromatics which have a
cyclic structure with close ends. They are all unsaturated unlike the aliphatics that has a
mixture of saturated and unsaturated compounds. However, they behave like saturated
aliphatic compounds.

The aliphatic hydrocarbon are further grouped into three based on their functional groups as
alkanes, alkenes, and alkynes. Therefore the next question on your mind should be what is
functional group?

Also carbon atoms present in an organic compound are classified as primary (1o), Secondary
(2o) or Tertiary carbons.

A carbon that is bonded to only one other carbon atom is referred to as a primary carbon
when the carbon atom is bonded to two other carbon atoms; it is referred to as a 2o carbon.
When the carbon is bonded to three other carbon atoms, it is a tertiary carbon and when it is
bonded to four carbon atoms.
H H
1o 1o
H HH C H HH C HH
o
4 o
H C1 o C2 C
o C 2 C 3 C1 H
o o

H H H C H H H H
H

Self-Assessment Question(s) (SAQ)

What is the difference between Aliphatic and Aromatic hydrocarbon?

Self-Assessment Answers

Aliphatic hydrocarbons have the straight chain with open ends, while the Aromatics
which have a cyclic structure with close ends.

3.2 Functional Groups

37
The organisation of organic compounds is based on their functional groups because of its vast
number of different molecules.

The concept of functional groups is central in organic chemistry, both as a means to classify
structures and for predicting properties. A functional group is the part of a molecule where
most of its chemical reactions occur. It is the part that effectively determines the compounds
chemical properties and many of its physical properties as well.

A functional group can either be a bond as in alkenes or alkynes, or a group of atoms in the
compound as in alkanols (-OH ) or acid (-COOH). The same functional group will undergo
the same or similar chemical reaction(s) regardless of the size of the molecule it is part of.
However, its relative reactivity can be modified by the size of the molecules or earby
functional group present also. The use of functional group makes the study of organic
chemistry systematic. By grouping similar compounds together in a class or family, it is
easier to identify them, and understand the chemical properties and reactions. A group of
organic compound with the same functional group is referred to as homologous series.

Self-Assessment Question(s) (SAQ)

Define homologous series?

Self-Assessment Answers

A group of organic compound with the same functional group is referred to as

homologous series.

3.3 Homologous Series

Homologous series is a group of compounds where each member differs’ from the next
member by a constant unit. For example alkanes members differ from each other by a
constant unit of CH2

Methane – CH4
Ethane – CH4 + CH2 = C2H6
Propane – C2H6 + CH2 = C3H8

They have similar method of preparation, their physical and chemical properties are the same
though with a progressive change due to the increase in the size of their molecules.
Members of a homologous series are called homologous. Below are various homologous
groups in organic chemistry.

38
Self-Assessment Question(s) (SAQ)
Define homologous series?

Self-Assessment Answers

Homologous series is a group of compounds where each member differs’ from the next
member by a constant unit. For example alkanes members differ from each other by a
constant unit of CH2.

4.0 Conclusion

The classification of organic compounds and the understanding of functional groups in

organic compounds makes it easier to understand the chemistry of organic compounds and
the trends in their physical behaviour.

5.0 Summary
1. Organic compounds are classified based on many factor including composition,
reactivity, chain type etc.
2. Carbon atoms in an organic compound are classified as 1o,2o,3o or 4o
3. Functional groups are bonds or group of atoms which determines the chemical
reactivity of the homologous group.
4. Homologous series are group of compounds with similar chemical and physical
properties.

6.0 Tutor Marked Assessment

39
 List the functional group present in each of the compounds below.

H O H H
H H ;
i. H C C ; ii. C C C H ; iii. H C C
H H H OH
H H O
iv. H C C C
OH
H H

Give the name of the homologous group of the compounds in “1” above.?
Define homologous series?
Classify the carbon atoms in the compounds below?

7.0 Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

40
 Unit 4
Structural Formula and
Nomenclature
Contents
1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 The Structural Theory of Organic Chemistry
3.2 Isomerism
3.3 IUPAC Nomenclature of Organic Compounds
4.0 Conclusion
5.0 Summary
6.0 Tutor Assessment Exercise
7.0 Reference

41
1.0 Introduction

Organic molecules are commonly described more by structural formulae, which combine
drawings and chemical symbols. Also the names of organic compounds are systematic and
are based on the identification of the parent structure. These two topics give a good
representation of an organic compound.
In this unit, you will study how to write correct structure and names of organic compounds.

2.0 Learning Outcomes

At the end of this unit, the student should be able to;

1. Draw structural formula

2. Give a condensed form of any compound.
3. List for function group in a compound
4. Define isomerism, Homologous series, and functional group.
5. Identify the functional group present in a compound.
6. Identify the longest chain of an organic compound.
7. Name any organic compound.
8. List the rules for naming any organic compound.

3.0 Learning Content

3.1 The Structural Theory of Organic Chemistry

August Kekule Archibald Scott Couper and Alexander Buttlerov laid the basis for the
structural theory. In this theory two things are fundamental;

The atoms of the elements in organic compounds can form a fixed member of bonds. The
measure of this ability is called valence, carbon is Tetravalent; that is, carbon can form four
bonds. That implies that a carbon atom can use one or more of its valences to form bonds to
other carbon atoms.

42
In a sp3 hybridised carbon atom, all four valences are used in bonding to four different atoms.
In a sp2 hybridised carbon atom, two of the bonds are used in forming the C = C double bond,
which make the molecule unsaturated. Leaving the remaining two for other atom(s). In a sp
carbon, three of the bonds are use in forming the C ≡ C (triple bond), leaving just one bond
for another atom.

Therefore in drawing the structure of an organic compound, all valences of any atom
involved must be accounted for.

Self-Assessment Question(s) (SAQ)

What is the difference between sp3 and sp2 hybridization?

Self-Assessment Answers

In a sp3 hybridised carbon atom, all four valences are used in bonding to four different
atoms while, In a sp2 hybridised carbon atom, two of the bonds are used in forming the C
= C double bond,

3. Writing Structural formulas

There are three ways of writing the structural formulae:
1. The dash formula;
2. The condensed formula; and
3. The line formula
4. The dash formula

A dash formula is like the Lewis structure of a given molecular formula expressed in a two
dimensional form dash formula shows how the atoms are connected to each other. For
example C2H6

H H
Molecule formular

C2H6 H C C H

H H
H H H
C3H8
H C C C H

H H H

43
 3.1.1 Structural Formulae of Organic Molecules

Structural formulae show how the atoms within organic molecules are joined together by
various chemical bonds (single, double or triple) and in some case, how the atoms and bonds
are arranged in 3 – dimensioned space.
It is possible to draw the structural formula of an organic compound in several different ways
when a molecular formula is given. By convention, a single straight line connecting the
atomic symbols is used to represent a single bond, two of such lines represent a double bond
and three lines represent a triple bond. It is the representation of compounds by these symbols
that is called structural formulas; some examples are:

H H H
H
H C C H
C C
H C C H
H
H H
H H O
H
O C O
H C N C C
C O H

H H OH

Different Ways of Drawing Structural Formulae

There are three way of writing the structural formulae:

1. The dash formula

2. The condensed formula
3. The line formula

3.1.2 The Dash Formula

The illustrations above are examples of a dash formula. A dash formula is like the Lewis
structure of the molecule expressed in a two dimensional form. Dash formula shows how the
atoms are connected to each other.

H H H H H O
H H
H C C C C H H C H
H H H H H H Cl
l

C C C
44
 C4H10
C4H7ClO
Use of the dash formulae is common and very helpful when studying organic chemistry and
working out molecular structures. It helps bring out hiding information about the molecule
formulae like this do not show the actual shape of the molecule but show only how they are
connected.

3.1.3 Condense Formulas

To save space and time in the representation of organic structures, it is common practice to
use “Condensed Formulae” in which the bonds are not shown explicitly. In condensed
formulas, all the hydrogen atom or other atoms that are attached to a particular carbon are
usually written immediately after the carbon list the hydrogen atom(s) first. For example;

H H H H CH3CHCH2CH3 or CH3CHClCH2CH3
H C C C C H Cl
Dash Condensed
H C H H
Formula Formula
l
H H H O H
CH3CHOHCH2COCH3
H C C C C C H
H OH H H

Depending on the level of simplicity, branched bond may or may not be shown as in the first
example above.

3.1.4 Bond-line Formulas

This method dispenses with the symbols for carbon and hydrogen atoms and leaves only the
lines in the structural formula, although line formulas are employed mostly for cyclic (ring)
structures, its use for open chains structure, is becoming increasingly popular. It is the
quickest of all formulas to write because it shows only the carbon skeleton. The number of
hydrogen atoms necessary to fulfil the carbon atoms valences are assumed to be present, but
do not write them. Other atoms (O, N, S, Cl) are written. Each intersection of two or more
lines and the end of a line represent a carbon atom. For example;

45
 CH CH
3 2

CH CH =
CH3CHCLCH2CH3 =
3
Cl
CH Cl
2 =
CH CH
2 2

CH
2
CH CH
2 2 =
CH CH
2 2
CH
2

Multiple bonds are also indicated in bond-line formulas. This is one advantage of bond line
over the condensed formulas

CH 2 CH
CH3 =
C CH2

CH3

CH CHCH2 OH =
2
OH

Self-Assessment Question(s) (SAQ)

i. Give the structural formula for the compounds below; CH4; C2H6; C3H6; C4H6.
ii. Give the condensed formula for the structures below

3.2 Isomerism

Isomerism is defined as a phenomenon in which different compounds have the same

molecular formulas but different structural formulas. Molecules that exhibit this phenomenon
are refered to as isomers. For example

46
 H H H H H

C4 H10 = H C C C C H and CH3 C CH3

H H H H CH3
C4H6 O = CH3 –O –CH3 and CH3 –CH2 –O –H

As the number of carbon atoms increases, the chances and number of isomers possible
increases too, also as the bond types become more complex, the number of possible isomers
also increases. Isomer do not have the same chemical and physical properties.
There are different types of isomers. These include:

1. Position or structural isomers

2. Stereo isomers

Position isomers are those compounds having the same number and kind of atoms but
different bonding arrangement as in the above examples.
Stereo isomer occurs due to restriction of rotation around double bond. Therefore stereo
isomers occur mainly in compounds containing double bonds.

Cl Cl H Cl
C C
C C
Cl H
H
H Trans
Cis

The two compounds differ only in the arrangement of their atoms in space. Stereo isomers
will be discussed more in unit 7.
Self-Assessment Question(s) (SAQ)
State the three ways of writing organic structural formula?
What are the different types of isomers?

Self-Assessment Answers

1. The dash formula

2. The condensed formula
3. The line formula

1. Position or structural isomers

2. Stereo isomers

47
3.3 IUPAC Nomenclature of Organic Compound

The naming of organic compounds is very systematic. Because of the large number of
different types of organic compounds, naming of each must be very explicit and identifiable.
The IUPAC system of naming organic compounds has three important parts which are the
suffix, main name and the prefix. Just like every human name, to identify anybody by name,
a complete name must have a surname, first name and other name, same in names of organic
compounds. The surname is family names which represent the homologous group the
compound belongs; the first name is the parent structure which is the longest carbon chain in
the compound. While the other names are the branching present in the compound, this is just
an analogy to the human name.

The IUPAC nomenclature has some simple rules that must be obeyed to obtain an
unambiguous name of an organic compound. However, proper naming will be done as we
treat each homologous series. The general rules we must know:
First identify the functional group present that will determine the chemical properties of the
compound that will be the family name e.g.

C –C –C –C C –C –C = C
alkane alkene

Identify the longest continuous carbon chain. In the case where a multiple bond is present in
the compound, the multiple must be part of the longest chain. This chain forms the parent
hydrocarbon.

Identify the branches on the parent chain and number the carbon atoms in longest chain
earlier identified e.g.
C
C C

C–C–C–C–C–C

The numbering must give the lowest combination of the positions of the branches identify.
As in above example, the number combinations can either be 346 or 356, but 346 is lower
therefore is used in naming.

48
Bearing these gets of rules in mind, each homologous group has additional rules before you
can give a correct and unambiguous name to a compound.
Self-Assessment Question(s) (SAQ)
What are the three important parts in using the IUPAC system of naming organic
compounds?

Self-Assessment Answers

The suffix, the main name and the prefix.

4.0 Conclusion

The structural formulas of organic compounds helps to bring out hidden information at a
glance. Understanding the writing of structural formulas and nomenclature in organic
chemistry is a big step to understanding the course.

5.0 Summary
1. Structural formulas are representation of organic molecules showing the connection
between atoms.
2. Three different ways of writing structural formulas are the dash, condensed and bond-
line formulas
3. Isomerism is the phenomenon in which different compounds have the same molecular
formulas but different structural formulas.
4. Organic compounds are named based on some set of rules which include identifying
the functional group present, the longest chain of carbon atoms possible and the
branches.

6.0 Tutor Marked Assignment

49
i. Give the condensed and line formulas of the following compounds

H H H CH3 H CH2
C2H5 H H C2H5 CH2
CH2
H C C C C C H ; C C C C C H ; CH2

H CH3 H CH3 H H H H CH3 H CH2 CH2

ii. Give the molecular formulas of the structures below

H C2H5 H CH3
CH2C(CH3)CH2CH3 ; ; H C C C C H
H H CH3 H

iii. Give the possible isomers of the following compounds;

CH(CH3)CH(C2H5) ; CH3CH2CH2CHCH2 ; C5H12

iv. State the type(s) of multiple bond(s) present in the compounds below

CH(CH3)C(CH3)CH2CCH ; C4H8 ; CH3CH2CCH ; C(CH3)4

7.0 Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

50
 Module 2
Introduction to
Hydrocarbons
Unit 6 - Alkane
Unit 7 - Alkene
Unit 8 - Alkyne
Unit 9 - Aromatic Hydrocarbon

51
 Unit 6
Alkane
Contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Source Of Alkane
3.2 Naming Of Alkanes And Cycloalkanes
3.3 Preparation Of Alkanes
3.4 Physical And Chemical Properties Of Alkanes
4.0 Conclusion
5.0 Summary
6.0 Tutor Assessment Exercise
7.0 Recommended Books

52
1.0 Introduction

Hydrocarbons, as the name implies, are compounds whose molecules contain only carbon
and hydrogen atoms. Compounds such as alkanes are refered to as saturated compounds
because they contain only single bonds as such, contain maximum number of hydron atoms.
Hydrocarbon that contains multiple bonds are said to be unsaturated. Therefore, alkanes are
those compounds in which all the carbon-carbon bonds are single bonds. Cycloalkanes are
alkanes in which all or some of the carbon atoms are arranged in close chain(ring) alkanes
and cycloalkanes are very similar in properties.

2.0 Learning Outcomes

Under this unit, we will learn the important chemistry of alkane family and at the end,
students should be able to:

1. Mention the sources of alkanes hydrocarbon

2. Give an IUPAC nomenclature of any saturated hydrocarbon
3. State the physical properties of alkanes homologous group.
4. Mention the reactions of alkanes
5. Describe the preparation of alkanes

3.0 Learning Content

3.1 Sources of Alkanes

The principal sources of akanes are natural gas and petroleum. Petroleum is a complex
mixture of organic compound, and remains useless until it is separated into its component
mixture. The act of separating petroleum into its components is known as refining. Complete
separation into individual component is economically impracticable and virtually impossible
technically. Therefore petroleum is refined into fractions based on volatility of its
components’. Refining of petroleum is all about fractional distillation of the oil. Many of the
distillates have almost the same boiling points therefore the fractions taken contain mixture of
alkanes of similar boiling points. Natural gas contain mainly methane, CH4 ,the simplest
member of the alkane family.
Self-Assessment Question(s) (SAQ)
What is the principal source of alkanes?
What is refining in hydrocarbons?
53
Self-Assessment Answers

The principal sources of akanes are natural gas and petroleum.

The act of separating petroleum into its components is known as refining

3.2 Naming Alkane Compounds

As earlier stated, alkanes are saturated hydrocarbons with C – C single bonds. They have a
general formular CnH2n+2 for open chain alkanes and CnH2n for cycloalkanes (close chains).
Carbon in alkanes and cycloalkanes are sp3 hybridised. They are enerally tetrahydral in
shape. The IUPAC system for naming alkanes is not difficult to learn and the principles
involved are used in naming compounds in other families as well.

3.2.1 Unbranched Alkanes

The names for unbranched alkanes are used as the primary source on which all other naming
depend and are given in the table below. The ending for all names of alkanes is –ane. The
stems of the names of most alkanes (i.e. parent structure) are of greek and latin origin.
Learning the stems is like learning to count in origin chemistry. Thus one, two, three, four,
five becomes methane - , eth -, prop - , but - , pen -. The simplest numberof the alkanes is
methane

Name Number of Carbon Atoms Structure

Methane 1 CH4
Ethane 2 CH3CH3
Propane 3 CH3CH2CH3
Butane 4 CH3(CH2)2CH3
Pentane 5 CH3(CH2)3CH3
Hexane 6 CH3(CH2)4CH3
Heptanes 7 CH3(CH2)5CH3
Octane 8 CH3(CH2)6CH3
Nonane 9 CH3(CH2)7CH3
Decane 10 CH3(CH2)8CH3

54
 3.2.2 Alkyl Group

When one hydrogen atom is removed from an alkane, an alkyl group is formed. These alkyl
groups have their names ending in yl. For example

H H

H C H H C H

Methane (alkane) methyl (alkyl)

H H
H H
H C C H H C C
H H
H H
Ethane Ethyl

Alkyl groups are sometimes represented with a capital letter R.

3.2.3 Naming Branched Alkanes

In line with the earlier mentioned rules in unit 5, branched alkanes are named according to
the following additional rules:
Identify the longest continuous chain of carbon atoms; this chain determines the parent name

CH3 CH2 CH2 CH CH3

CH2
CH3
for the compound.

Please note that the longest chain may not always be obvious from the way it is written. Any
carbon not on the chain identified is regarded as a substituent or branched and all substituent
are alkyl groups and should be named accordingly.

Number the longest chain beginning with the end of the chain nearer to the substituent.
6 5 4
CH3 CH2 CH2 3
CH CH3
2
CH2
1
CH3

55
Use the numbers obtained in (ii) to designate the location of the substituent group. In the case
of the example above, 3 is the position of the substituent group. Therefore, the name of the
6 5 4
CH3 CH2 CH2 3
CH CH3
2
CH2
1
CH3
3 Methylhexane
compound is;

When two or more substituent are present, give each substituent a number corresponding to
its location on the longest chain and the substituent are listed in alphabetical order without
considering the “di” or “tri” for repeating substituent

CH3 CH CH2 CH CH2 CH3

CH3 CH2
CH3
4-Ethyl-2-Methylhexane
When two substituent are present, give each substituent a number twice and when
substituents are identical, it is indicated by using the prefixes di-, tri-, tetra-, CH3 and so on.

CH3
CH3CH2 C CH2CH3
CH3

2,2 - Dimethylpentane

CH3 CH3
CH3 C CH CH CH3
CH3 CH3
2,2,3,4 - tetramethylpentane

56
When branching first occurs at an equal distance from either end of the longest chain, choose
the name that gives a lower combination of number.

CH3 CH CH2 CH CH CH3

CH3 CH3 CH3
2,3,5 - trimethylhexane and
not 2,4,5 - trimethylhexane

3.2.4 Naming Cycloalkane

Cycloalkanes with only one ring are attaching the prefix cyclo to the names of the alkane
possessing the same number of carbon atoms.

H2C CH2

=
Cyclopropane
CH2

H2C CH2

H2C CH2 =
CH2
Cyclopentane

Using the line structural formula for cyclo compounds is easier and more convenient. Naming
of substituted cycloalkane follow every other principle started earlier.

57
 C3H7
CH3

propylcyclohexane C2H5
1 - Ethyl - 3 - Methylcyclohexane
CH3
C2H5

2 - Ethyl - 1,4 - methylcyclohexane

(not 3 - Ethyl - 1,4 - methylcyclohexane)
CH3

When a ring is attached to an open chain with great number of carbon atoms the ring
becomes the substituent or when two or more rings are attached to a single chain, it is
appropriate to take the rings as branches.

CH2 CH2 CH2CH3

1,5- Dicyclopropylpentane

1 - Cyclopropylbutane

3.2.5 Naming of Branched Alkyl Group

Alkyl group are named just like the alkanes. The branched alkyl group naming follow all the
principles stated in 3.2.3 above but in addition, the numbering MUST start from the pint
where the group is attached to the main chain. For example
CH3
CH3 CH2 CH2 or CH3 CH
Propyl 1 - Methyl -
CH3 CH2 CH2 CH2 or CH3 CH2 CH or CH3 CH CH2

Butyl CH3 CH3

1 - Methylpropyl 2 - Methylpropyl

58
Self-Assessment Question(s) (SAQ)
The general formula of alkanes is?

i. Give the name of the following Alkanes

CH3
C2H5
CH3CH2CH2CH2CH3 ; CH3CH2CH2CH2CH3 ;
C3H7 C3H7
CH3
Self-Assessment Answers

CnH2n+2 for open chain alkanes and CnH2n for cycloalkanes (close chains).

3.3 Preparation of Alkanes

In the laboratory, the preparation or synthesis of any particular alkane needed is the surest
way of obtaining alkane because alkanes obtained from petroleum source are in mixture and
can only be used as fuel.

Source of the methods used in the preparation will be outlined here.

1. Hydrogenation of Alkenes and Alkynes

Alkenes and Alkynes react with hydrogen in the presence of metal catalyst such as nickel and
platinum to produce alkanes.

H2C CH2 + H2 CH3 CH3

HC CH + 2H2 CH3 CH3

2. Reduction of Alkyl Halides

Most alkyl halides react with zinc and aqueous acid to produce an alkane.

R X+Zn+HX R H+ZnX2
or
Zn / HX
R X R H

59
Specific examples

Zn
2CH3 CH2 CH CH3 HBr 2CH3 CH2 CH CH3 + ZnBr2

Br H

CH3 CH3
Zn
2CH3 CH CH2CH2 HBr 2CH3 CH CH2CH2

Br H

3. Alkylation of Terminal Alkynes

Alkyl group is used to replace a hydrogen terminal alkyne and then hydrogenated. Such
hydrogen are refered to as acetylenic hydrogen which are weakly acidic and can be removed
with a strong base such as sodium amide.

R X
R C C H
NaNH2
R C C: - Na + R C C R1

R – X Must be a methyl or primary and un-branched at the second carbon.

Example

CH3 CH3 CH3

NaNH - + CH3Br
CH3 CH C CH C - NH23 CH3 CH C C: Na NaBr CH3 CH C C CH3
Ni / 2H2

CH3
CH3 CH CH2 CH2 CH3

Self-Assessment Question(s) (SAQ)

60
 How are alkyl formed?
i. Describe one method of preparing a named alkane?
ii. Give the name of the catalysis used in the hydrogenation of C2H4 ?

Self-Assessment Answers

When one hydrogen atom is removed from an alkane, an alkyl group is formed.

3.4 Physical And Chemical Properties Of Alkanes

3.4.1 Physical Properties

At room temperature, the first four members of the alkane family are gases; C 5 – C17 are
liquids and the rest are solids. Boiling points of the unbranched alkanes show a regular
increase with increasing molecular weight. Branching of the alkanes chain lower the boiling
point.

Melting point – the unbranched alkanes do not show the same mooth increase in melting
points with increasing molecular weight.

Density – alkanes are the least dense of all groups of organic compounds. All alkanes and
cycloalkanes have densities considerably les than 1.00gml -1

Solubility – Alkanes and cycloalkanes are almost insoluble in water because of their very low
polarity and their inability to form hydrogen bonds. They are soluble in organic solvents.

3.4.2 Reactions of Alkanes

Alkanes are inert to most reagent since they are saturated. However, it can undergo
substitution and combustion reaction.
Substitution Reaction is the successive replacement of it hydrogen atoms by halogens.

CH4 + Cl2 CH3Cl + HCl

C2H6 + HCl C2H5CL + H2

This reaction can continue until all the hydrogen atoms are completely replaced.
Combustion Reaction

61
Alkane reacts vigorously with oxygen when an appropriate mixture is ignited. The reaction is
exothermic and the reactivity increases with increasing branching. That is while branched
chain isomers improve the quality of petrol.

The combustion of alkanes give carbon dioxide and water.

CH4 + O2 CO3 + H2O

Cracking – it is the breaking down of higher molecular alkanes into smaller molecules. It has
application in petroleum industries where it is used to increase the quality and quantity of
petrol fractions.

Self-Assessment Question(s) (SAQ)

i How are cyclic alkanes named?
How are acetylinic hydrogen formed?

Self-Assessment Answers

Cycloalkanes with only one ring are attaching the prefix cyclo to the names of the alkane
possessing the same number of carbon atoms.
When an alkyl group is used to replace a hydrogen terminal alkyne and then
hydrogenated. Such hydrogen is refered to as acetylenic hydrogen.

4.0 Conclusion

Alkanes are very important member of the organic compound as they form the based upon
which other homologous series are derived. The understanding of alkanes simplifies a lot of
other topic to be encountered.

5.0 Summary
1. Alkanes are naturally derived from natural gass and petroleum.
2. Alkanes are saturated organic compounds with sp3 carbon atoms.
3. Naming of alkanes and cycloalkanes help in the naming of other compounds to be
treated.
4. Alkanes are prepared by hydrogenation of unsaturated hydrocarbon, reduction of alkyl
halides and alkylation of terminal alkynes.
5. Alkanes undergo substitution and combustion reaction only.

62
6.0 Tutor Marked Assignment

1. State two physical properties of alkanes.

2. Give the IUPAC nomenclature of the following alkanes.

CH3

i. ii. CH CH CH C(CH )CH

3 2 2 2 3
iii.

CH3 CH3

iv. v. C(CH3)4

Describe the preparation of any alkane from a named terminal alkyne

7.0 Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.
Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.
Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

63
 Unit 7
Alkenes
Contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Geometric Isomers in Alkenes
3.2 Nomenclature of Alkenes
3.3 Preparation of Alkenes
3.4 Physical Properties of Alkenes
3.5 Chemical Reaction of Alkenes
4.0 Conclusion
5.0 Summary
6.0 Tutor Assessment Exercise
7.0 Recommended Books

64
1.0 Introduction
Alkenes are hydrocarbons with carbon – carbon double bond (C = C). The double bond
serves as the functional group of the homologous family known with the old name as Olefins.
Alkenes have a general formula CnH2n and CnH2n-2 for open and closed chains respectively.
They are unsaturated so very reactive. In this unit, you will learn the properties of the alkenes
their reactions and synthesis. Also you will learn to name a double bond alkene compound.

2.0 Learning Outcomes

At the end of this unit, you should be able to:

1. Name most alkene compound.
2. Describe the preparation of alkenes
3. List the physical properties of alkenes.
4. Describe some important reactions of alkenes.

3.0 Learning Contents

3.1 Geometric Isomerism

Isomerism was defined in unit 4, however geometric isomerism is peculiar to alkane
compound. Isomer have the same molecular formula but different structural formula. Due to
restriction rotation around a double bonds, compounds exhibit a new type of isomerism,
refred to as stereoisomerism. The two compounds differ only in the arrangement of their
atoms in space. for example

Cl Cl Cl H
C C and C C
H H H Cl
Cis - 1,2 - dichloroethene Trans - 1,2 - dichloroethene

The difference in the two molecules is indicated by attaching the prefix cis or trans to their
names.
Geometric isomerism does not exist when the substituent on a carbon atom of the double
bond are the same for example

H CH3
C C
H H

65
Self-Assessment Question(s) (SAQ)
When do we experience the absence of geometric isomerism?

i. In which of the following compounds will geometric isomerism exist?

CH3CHC(CH3)2 ; CH3 CH2 CHCH(CH3)

ii. How many isomers will the molecular formula give?

CH3CH2CH2CHC(CH
Self-Assessment 3)CH3
Answers

Geometric isomerism does not exist when the substituent on a carbon atom of the double
bond are the same.

3.2 Nomenclature for Alkenes

The IUPAC rules for naming alkenes are similar in many ways to those for naming alkanes
with some additional rules as given below;
Determine the parent name by selecting the longest chain that contains the double bond and
change the ending of the name of the alkane of identical length from – ane to – ene e.g.

H2C C CH2 CH3

CH2
CH3
2 - ethyl butene

Number the chain so as to include both carbon atoms of the double bond and begin
numbering at the end of the chin nearer to the double bond. Show the position of the double
bond y using the number of the first atom of the double bond as a prefix.

CH3 CH CHCH2CH2CH3

2 - Hexene (not 4 - hexen)

66
Number substituted cycloalkene in the way that gives the carbon atoms of the double bond
the 1 and 2 positions and that also gives the substituent groups the lower number possible,
e.g.

CH3
1
5 2

4 3 CH3 CH3
1 - Methyl cyclopentene 3,5 - dimethyl cyclohexene
(not) 2 - methyl cyclopentene (not 4,6 - dimethyl cyclohexene
If two identical groups are on the same side of the double bond, the compound should be
designated cis ; if they are on opposite sides it should be designated trans

Cl Cl C2H5
CH3
C C and C C
H H Cl Cl
Cis - 1,2 - dichloroethene Cis - 2,3 - dichloropentene

Self-Assessment Question(s) (SAQ)

i. Give the name of the possible isomers of the molecule C5H10

3.3 Preparation of Alkenes

Alkenes are prepared by elimination reactions, some of which are give below:
Dehydrohalogenation of Alkyl halides.

H H
H H
base
H C C H HX C C

H X H H

In this reaction, KOH in alcohol or sodium alcohol can be used and alkene is produced.
Dehydration of Alcohols.

H H
H H
H+, heat
H C C H HOH C C

H OH H H

67
Heating most alcohol with a strong acid causes them to lose a molecule of water and form an
alkene. Conc. H2SO4 is mostly used for this reaction.
Debromination of dibromides

Br H
H H
base
H C C H C C

H Br H H
A
compound with two molecules of halogen in which the halogens are situated on adjacent
carbon atoms refered to vicinal (or vic) are used for this reaction in the presence of a base.

Self-Assessment Question(s) (SAQ)

What effect does heating alcohols produce?
1. Give the product of the reaction C3H7OH with H2SO4 on heating?
2. Mention two ways of preparing a name alkene in the laboratory.

Self-Assessment Answers

Heating most alcohol with a strong acid causes them to lose a molecule of water and form
an alkene.

3.4 Physical and Chemical properties of Alkenes

3.4.1 Physical Properties

Alkenes are similar to alkanes. The first four members of the group are gases at room
temperature.

Alkenes dissolve in non-polar solvents, though they are slightly soluble in water. Alkenes
have density lower than that of alkanes cis and trans isomers of alkenes do not have the same
stability, the greater the number of attached alkyl groups, the greater is the alkene stability.

3.4.2 Reaction of Alkenes

The unsaturated hydrocarbon are chemically more reaction than the alkanes. Their reaction is
centre around the double bond. Alkenes undergo the following reactions:

68
Reaction with Hydrogen (Hydrogenation)

H H
H H Ni or Pt
C C + H2 H C C H
H H H H

Reaction with Halogens( Halogenation)

H Br
H H CCl4
C C + Br2 H C C H
H H Br H

Reaction with Hydrogen Halides

The reaction of hydrogen halides with alkene obeys markovnikov’s rule which states that
when an unsymmetrical molecule reacts with an unsymmetrical alkene compound, the more
electronegative atom or group become attached to the highly substituted carbon atom of the
double bond while the more electropositive atom or group become attached to the less
substituted carbon.

For example, ethene is a symmetrical molecule but propene is not therefore a reaction of
propene and hydrogen bromide will obey Markovnikovs rule as shown below

H H H
H H
H C C C + H - Br2 H C C C H
H
H H Br H
2 - bromopropane

Reaction with halic acid.

Please note that bromopropane is also produced alongside but mopropane predominates

69
 Aqueous solution of halogens are refered to a halic acid, (X – OH) e.g. HOCl, HOBr

H H
H H -
δ+
δ
C C + HO Br H C C H
H H OH Br
H H H
H H
H C C C + HO - Br H C C C H
H
H H OH Br

Reaction with Conc. H2SO4

The reaction of alkenes with H2SO4 yield alkyl hydrogen sulphate which gives alkanols

H H H OSO3H H OH
δ +
C C + H OSO3H H C C H H C C H
H H H H H H

When heated in water (hydrolysis). This reaction obeys markovnikov rule.

H H H H H H
H2 O
C C C + H OSO3H H C C C H heat H C C C H
H OSO3H H H OH H
2 - propanol

Reaction with KMnO4

Alkene reacts with KMnO4 in water to give a diol (that is an alkanol with two – OH groups)

H H H H
C C + KMnO4 H C C H
H H H OH

70
Alkenes also react with oxygen to give carbon dioxide and water

H H
C C + 3O2 CO2 +H2O
H H
or reat in limited oxygen to give an eoxide

H2C CH2
H H
C C + 1/2O2
H H
O

Ozonolysis of Alkenes

Ozonolysis is a reaction of alkenes with ozone molecule. It is a widely used reaction to locate
the position of a double bond in an alkene compound. In this reaction, ozone react vigorously
with alkenes to form unstable compound which rearrange spontaneous to from a compounds
known as ozonides. The ozonides quickly hydrolyses to form either aldehydes or ketones
depending on the position of the double e.g.

H H H H
O3, CH3Cl2
H C C C or Zn / HOAC
C C O+ O C H
H H H aldehydes

CH3 CH3 H
C C CHCH3 CH3 C O + O C CH3
ketone aldehyde

Self-Assessment Question(s) (SAQ)

What is Markovnikov’s rule?
Give the products of the reactions of propene with the following;
I. HCl
II. I2/CCl4
III. Conc. H2SO4
IV. Acidified KMnO4

Self-Assessment Answers

Markovnikov’s rule which states that when an unsymmetrical molecule reacts with an
unsymmetrical alkene compound, the more electronegative atom or group become
attached to the highly substituted carbon atom of the double bond while the more
electropositive atom or group become attached to the less substituted carbon.

71
4.0 Conclusion

You have study the chemistry of alkene family. The nomenclature, preparation and chemical
reactions will be very useful in the study of other homologous families yet to be encountered.

5.0 Summary
1. Alkenes are hydrocarbons with C=C double bond unsaturation with a general formula
CnH2n and CnH2n-2 for open and close chain respectively.
2. Due to restricted rotation around the double bonds alkenes exhibit a geometric
isomerism.
3. In naming alkenes, the position of the double bond must be indicated.
4. Alkenes are prepared by;
5. Dehydrohalogenation of alkylhalides.
6. Dehydration of alcohols.
7. Debromination of dibromides
8. Alkenes undergoes vary chemical reaction to give different products as illustrated in

6.0 Tutor Marked Assignment

1. Give the names of the following compounds;

- CH3 - CH2 CH = CH2

CH3

C2H5
- C C C C C C

CH2 CH2

CH3

-
CH3
2. Describe the preparation of a named alkene by the dehydration

72
7.0 Recommended Books
Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

Unit 8
Alkynes
Contents

73
1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Nomenclature Of Alkyne
3.2 Preparation
3.3 Physical Properties And Chemical Reaction
4.0 Conclusion
5.0 Summary
6.0 Tutor Assessment Exercise
7.0 Recommended Books

1.0 Introduction

Hydrocarbon compounds containing a triple bond carbon atoms (C≡C) are refered to Alkyne
the triple bond is the functional group of this homologous family carbon atom with a triple
bond has sp hybridization with a bond angle of 180oC. Therefore in this unit, you will learn
the naming of the compounds with C≡C, their preparations and the reactions.

2.0 Learning Outcomes

At the end of this unit, you should be able to give the:

1. Names of alkyne compounds
2. Describe the preparations of alkynes
3. List and describe the reactions of alkynes

74
3.0 Learning Contents

3.1 Nomenclature of Alkyne

Alkynes are named in much similar way as alkenes. Un-branched alkynes are named by
replacing the – ane of the corresponding alkane with the ending – yne. The chain is numbered
to give the carbon atoms of the triple bond the lower possible number.

The lower number of the two carbon atoms of the triple bond is used to show the position of
the triple bond.

H3C CH2 C CH H C C H
1 - butyne ethyne

For branched alkynes, the locations of the substituent groups are also indicated with numbers.

CH3CHCH2CH2C CH CH3
CH3C CH2C CH
CH3
CH3
5 - methyl - 1 - hexyen 4,4 - Dimethyl - 1 - pentyne

Note that mono-substituted ethyne or 1 – alkynes are called terminal alkynes and the
hydrogen attached to the carbon of the triple bond is called the acetylenic hydrogen.
acetylenic hydrogen
R C C H
a terminal alkyne

Self-Assessment Question(s) (SAQ)

Give the bond line structure of any two isomers of the alkyne compounds below
and the name of the compounds; C4H6; C(CH3)3 C CCH3; C6H8

3.2 Preparation of Alkynes

Alkynes can be prepared in the laboratory in pure form as follows:

Dehydrohalogenation of vic-dibromides to form alkynes from alkenes

75
 2NH2
C C + Br C C H C C H+H N H + HBr
Br Br H

Ketones can be converted to dichloride using phosphorous pentachloride

The product of this reaction is used to synthesize alkyne
O Cl
C CH3 C CH3 C CH
PCL5 Cl NaNH2
o
0C -POCl3 mineral oil heat

Replacement of aetylenic hydrogen atom.

This method is use to extend the length of an alkyne chain
NaNH2 R1CH2 Br
CH3C C H Liq. NH3 CH3C C:- Na+ CH3C C CH2R1+ NaBr

Self-Assessment Question(s) (SAQ)

How are alkynes prepared?
i. Using equation only show the preparation of alkyne by acetylenic
hydrogen atom replacement.

Self-Assessment Answers

Alkynes can be prepared in the laboratory in pure form as follows:

Dehydrohalogenation of vic-dibromides to form alkynes from alkenes

3.3 Physical and Chemical Properties of Alkynes

3.3.1 Physical Properties

Alkynes are similar, behave similarly to the alkenes. The homologous family has the general
formula CnH2n-2. The simplest alkyne is the ethyne. They have density lower than that of
alkenes and alkanes.

3.3.2 Chemical Reaction of Alkynes

76
Alkynes undergo addition reaction like the alkenes, however with more reagent and greater
reactivity. Additional reactions of the alkynes are given below:

Addition of halogen in the presence of the halogen compound of Iron (iii)

X X
2X2/FeX3
CH3CH2C CH CH3CH2 C C H
X X
Br Br
e.g. 2Br2/FeBr3
CH3C CH CH3C C H
Br Br

1,1,2,2 - tetrabromopropane

Reaction of alkynes with water.

Alkynes react with water to form an enol (that is a double bond unsaturated alkanol) the enol
is unstable and undergo rearrangement to form an aldehyde or ketone. Both isomers then
exist in equilibrium.

H OH H O
HgSO4 /H2SO4
HC CH C C C
60o H C
H H H H

The phenomenon where a pair of isomers exist in dynamic equilibrium with each other is
known as tortomerism. The isomers are called tortomerism.
Alkyne under go combustion reaction with oxygen to give carbon dioxide and water.

HC CH + 2 / O2
1
2
2CO2+H2O

Alkynes react with O3 to give carboxylic acids.

O O
O3
CH3C CCH2CH3 CH3C +CCH2CH3
OH HO

Self-Assessment Question(s) (SAQ)

What’s the effect of reaction of alkynes with water?

i. Give the final products of the reactions;

HgSO4/H2SO4
HC CH 60oC

O2
CH3 C CH
77
2Br2 / FeBr2
CH3 CH2 C CH
Self-Assessment Answers

Alkynes react with water to form an enol.

4.0 Conclusion

From this unit we have been able to learn the nomenclature of alkynes their preparations and
chemical reactions. Knowledge of these unit will be very useful in the learning of other units.

5.0 Summary
1. Alkynes are hydrocarbons with a triple bond unsaturation .
2. Alkynes are named in the same way the alkenes are named.
3. Alkynes are prepared by:
4. Dehydrogenation of vic dibromides
5. Dichlorination of a ketone.
6. Replacement of an acetylenic hydrogen atom
7. The reaction of alkynes involve:
8. Halogenations
9. Hydrogenation
10. Combustion
11. Due to the presence of the triple bond, alkynes are more reactive than alkanes and
alkenes.

6.0 Tutor Marked Assignment

1. Give the missing product in the reaction below;

NaNH2 C2H5 CH2Br
CH3CHC C H Liq. NH3 ? ? + ?

78
2. Give the IUPAC nomenclature of the compound below;

CH2CHCH2CCH ; CH3CH2CCCH2CH3 ; CH3CCH

3. Give the possible isomers of the molecules below;

H H
C5H8 ; CH3CH2CHC(CH3)CH3 ;
C C C C H
H

4. Describe the preparation of a named alkyne.

7.0 Reference

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

79
 Unit 9
Aromatic Hydrocarbons
contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Sources of Aromaticity In Aromatic Hydrocarbon
3.2 Nomenclature of the Aromatic Group
3.3 Preparation of Aromatic Compounds
3.4 Physical Properties and Chemical Reactions
4.0 Conclusion
5.0 Summary
6.0 Tutor-Marked Assignment
7.0 Recommended Books

80
1.0 Introduction

Aromatic compounds are unsaturated compounds, yet they do not easily partake in addition
reactions. Instead they undergo electrophilic substitution. In this unit, you will learn the
characteristic of aromatic compound, their reactions and preparation.

2.0 Learning Outcomes

At the end of this unit, you should be able to:

1. Define what aromaticity is
2. Give examples of aromatic compound
3. Give the names of some aromatic compound
4. Describe some reactions of aromatic compound
5. State some properties of some member of the group

3.0 Learning Content

3.1 Aromaticity of Aromatic Compounds

Aromaticity is the property characteristic of aromatic compounds. The properties arise

because the electrons in the π – orbitals are delocalized. Benzene is the simplest member of
this group it has an hexagonal ring of carbon atoms. The structural formula of benzene as
kekule show that it has three double bonds and three single bonds. However, experimental
evidence shows that all bonds in a benzene ring are the same .due to the delocalization of the
π – electron over the ring, giving it an extra stability. The condition for such delocalization is
that compound should have (4n+2) pi electron. This determines the aromaticity of the
compound and its stability.

resonance

delocalized multiple bond

81
The delocalization of the pi-electrons makes the ring stable towards addition reaction.
Resonance is a phenomenon whereby a molecule can be represented by two or more structure
which differ only in the arrangement of their electrons.
Characteristic Feature of Aromatic Compounds
 They are cyclic
 They are unsaturated
 They posses delocalized pi electrons system above and below the plane of the
molecule.
 The delocalized pi – electron cloud contain (4n+2)π electron. For benzene n=1.

Self-Assessment Question(s) (SAQ)

What is acylation?
1. Give the resonance structure of benezen.
2. List two characteristics of aromatic compounds.

Self-Assessment Answers

The group is called an acyl group and a reaction whereby an acyl group is introduced into
a compound is called an acylation.

3.2 Nomenclature of Benzene and its Derivative

The naming of benzene and its derivatives can be done in two ways;
The benzene is the parent name and the substituent is simply indicated by a prefix e.g.

F Cl Br

Fluorobenzene Chlorobenzene Bromobenzene

The other method is that the substituent and the benzene ring taken together may form a new
parent name for example.

Methylbenzene is called toluene

Hydroxybenzene is called phenol
Aminobenzen is called aniline

82
 CH3 OH NH3

Toluene Phonol Aniline

When two substituents are present, their relative positions are indicated by the prefix ortho,
meta and para (abbreviated O-, M- and P-) or by the use of numbers for example

Br Br
Br

Br Br
Br
1,2 - dibromobenzene 1,3 - dibromobenzene 1,4 - dibromobenzene
(o - dibromobenzene) (m - dibromobenzene) (p - dibromobenzene)

When a substituent combine to give a new name, the position of substituent is taken to be 1
and the new name is used.

COOH SO3H F

O2N NO2
F

3,5 - dinitrobenzoic acid 2,4 - difluorobenzenesulfonic acid

When the C6H5 – group is named as a substituent, it is called a phenyl group the phenyl group
is often abbreviated as C6H5-, Ph- or ᴓ-.

CH3CHCH2CH2CH2CH3
Ph

CH3C = CHCH3
2 - Phenylhexane 2 - Phenyl-2-butene

83
The name benzyl is used for the phenylmethyl group and can be abbreviated as Bz

CH2
CH2Cl

Benzyl group Benzyl Chloride

Self-Assessment Question(s) (SAQ)

Give the nomenclature of the following compounds

CH3
CH2 CH3 CH2 OH

; ;
CH3

3.3 Physical and Chemical Properties of Benzene

3.3.1 Physical Properties

Benzene is a colourless flame able liquid with a boiling point of 80oC. It is insoluble and less
dense than water. It is toxic

3.3.2 Chemical Reactivity

Benzene ring and all other aromatic ring are electron rich, due to their delocalized pi-electron.
Therefore, an aromatic ring is nucleophilic which preserves the aromatic characteristic of the
ring

Reaction of benzene
Halogenations

Benzene reacts with halogens in the presence of lewis acid catalysis.

Cl

AlCl3
Cl2 + FeCl3 + HCl

Br
AlCl3
Br2 + FeCl3 + HBr

84
Nitration
Benzene reacts with Conc. HNO3 in the presence of Conc. H2SO4.

NO2

HNO3/H2SO4
50o

Nitrobenzene

Sulphonation

Fuming H2SO4 at ≈50oC or conc. H2SO4 is used to provide the electrophile SO32+

SO3H

Conc. H2SO4

Benzenesulfonic acid

Friedel craft creation (Alkylation)

This involve the replacement of an hydrogen atom with an alkyl group. Reagent used is R –
X/AlX3
R

R-X / AlX3

O
R C
4b. Acylation

The group is called an acyl group and a reaction whereby an acyl group is introduced into a
compound is called an acylation.

CH3 O
C

AlCl3
+ CH3COCl + HCl

Self-Assessment Question(s) (SAQ)

i. Give the product of friedel Craft Alkylation of benzene with, C3H7 Cl / AlCl3.
ii. Give the reagent required for the nitration of benzene.

85
4.0 Conclusion

The chemistry of aromatic compounds is an interesting. Though, it is unsaturated, it behaves

like the saturated alkane. Thereby limiting the kind of reaction it would have been expected
to undergo. This have shown to you the naming and kind of reactions the aromatic
compounds can undergo.

5.0 Summary

1. Aromaticity is the property of compounds with pi electrons.

2. Their unssturated electrons are delocalized giving them a special characteristic
functions.
3. The main member of this group is the benzene.
4. The reactions of benzene include halogenations, nitration, sulphonation and friedel
crakt reaction.

6.0 Tutor Marked Assignment

i. Give the product of the following reaction;

a.
Cl2 + AlCl3

HNO3/H2SO4
b. 50oC

R - Br/AlBr3

c.

86
ii. Give the names of the compounds below.

SO3H
CH2 C2H5 CH3

CH2 CH2 OH

7.0 Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

Module 3
87
Introduction to Non-
Hydrocarbons
Unit 1 - Halo-hydrocarbon
Unit 2 - Alkanol
Unit 3 - Aldehydes and Ketones
Unit 4 - Carboxylic Acid
Unit 5 - Other Important classes

88
 Unit 10
Halohydrocarbons
contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Classification of Halohydrocarbons
3.2 Nomenclature of Halohydrocarbons
3.3 Preparation and Reactivity
4.0 Conclusion
5.0 Summary
6.0 Tutor Marked Assignment
7.0 Recommended Books

89
1.0 Introduction

Halohydrocarbons are the group of hydrocarbon compounds with halogen derivatives. They
may be aliphatic or aromatic, saturated or unsaturated. In this unit, we will be learning the
chemistry of halohyrocarbons. This includes nomenclature, preparation and chemical
reactions.

2.0 learning Outcomes

At the end of the unit, you should be able to:

Give the correct names of halohydrocarbon;
Classify any halohydrocarbon as primary, secondary or tertiary halohydrocarbon;
Describe at least one preparation method of haloalkane;
Discuss the reactions of halohydrocarbons

3.0 Learning Contents

3.1 Classification of Halohydrocarbons

As earlier mentioned, halohydrocarbons are the halogen derivatives of hydrocarbons. When

the halogen derivatives is bonded to an aliphatic hydrocarbon and specifically alkanes, it is
referred to Alkyl halide. And when the halogen is bonded to an aromatic hydrocarbon it is
called Aromatic halides.

R – X represents an Alkyl halide while Ar – X represents Aromatic halides.

Alkyl halides are classified as being primary (1o), secondary (2o) or tertiary (3o). This
classification is based on the carbon atom to which the halogen is directly attached. If the
carbon atom that bears the halogen is a 1o or 2o or 3o carbon, then the haloalkalne is classified
as 1o or 2o or 3o haloalkane respectively.

H H H H CH3
H C C C H H3C C CH3 H3C C CH3
H H Cl Cl Cl
1o alkyl halide 2o alkyl halide 3o alkyl halide

90
Self-Assessment Question(s) (SAQ)
1. How are alkyl halides formed?
2. Write structural formulas for two constitutional isomeric primary alkyl bromide with
the formula C4H9Br.

Self-Assessment Answers

They are formed when the halogen derivatives is bonded to an aliphatic hydrocarbon and
specifically alkanes, it is referred to Alkyl halide.

3.2 Nomenclature of Halohydrocarbons

The naming of halohydrocarbons follows all the rules you have been used to with a few
additions which we will look into.

The halogen derivative(s) are considered as substituent to the identified hydrocarbon chain;
In the case when there are more than one halogens. If the halogen are the same, their
positions on the carbon is indicated, and then add the prefix to indicate the number of atoms
presents. i.e. di, tri, tetra e.t.c.

If the halogen are of different elements, the lower combination of number is used and the
name is written in alphabetical order. Also when they are alkyl substitutes, the number that
gives the lower combination is used and the alphabetical order is followed. Examples:

CH3CH2CH2Cl CH3CH2F CH3CH2CH2I

1-chloropropane fluoroethane 1-iodopropane

91

Br
 Cl H H H
H C C C C H
H H Cl
Chlorobenzene 1-Chlorobutene

Br
Cl H Br
H C C C C H
H CH3H H Cl
3-Chloro-2-methylbutene 4-Chloro-1,2-bromobenzene

Self-Assessment Question(s) (SAQ)

i.. Give the IUPAC names for all the isomers of C4H9Br
ii. Give the IUPAC names of the compound
Br

3.3 Preparation and Reactivity

3.3.1 Preparation

Halohyrocarbons are prepared by the substitution of an hydrogen atom and alkane or benzene
compound.

92
 H H H H
H C C H + Br2
Ni or Pt
H C C Br + HBr
1
H H H H

H H H H

2 H C C H + HBr H C C Br + H2
H H H H

H H H H
H C C Cl + POCl3
3 H C C OH + PCl5
H H
H H

3.3.2 Physical Property

Halohydrocarbos are polar in nature because of the carbon-halogen bond. As a result, they
have higher boiling point when compared to hydrocarbon of same mass. For any given alkyl
group, boiling point increases from fluorine to iodine due to their mass increment. They are
insoluble in water.

3.3.3 Chemical Properties

Halohydrocarbon undergoes Nucleophilic Elimination Reaction

1. Nucleophilic Substitution: involve the displacement of the halide ion by a nucleophile
(i.e. an electron rich reagent)
R – X + Nuc R – Nuc + X-
Example
(a) Reaction with water or Alkali
R – X + H2O Boil R – OH + HX (reaction is very slow)
R – X + NaOH Ethanol R – OH + NaX (reaction)
(b) Warmion (OR) (Williamson Ether Synthesis)
Reaction with Alkoxide
NA + ROH NaOR + H2
R – X + NaOR Alkanol R – OR + NaX
CH3Cl + CH3ONa CH3OCH3 + NaCl
(c) With Ammonia to produce amines
R – X + NH3 R – NH2 + HX
(d) With cyanide ion
R – X react to give nitrite
R – X + NaCN R – CN + NaX
CH3Cl + NaCN CH3CN + NaCl
(e) With metal derivatives of alkynes

93
 R – X + CuC=CH R – C = CH + CuX

2. Elimination Reactions: It involves the removal of hydrogen and halogen atom from
adjacent atoms in the alkyl halide. The product of an elimination reaction is an alkene. Strong
bases are employed as reagents.

H H

H C– C–H + NaOH H2C = CH2 + H2O + NaX

H H

Elimination reaction usually accompany substitution reaction. Reaction can be rearranged

such that one reaction predominates. In general, elimination is favoured by using a hot and
concentrated reagent and tertiary alkyl halide while substitution is favoured by low
temperature and diluted reagent and a primary alkyl halide.

CH3CHOHCH3 (79%)
dil NaOH
CH3CHCLCH3
low temp.
CH3CHCH2 (21%)

(3) Formation of Grinard Reagent (R – MgX)

R – X reaction with Mg turnings,

Dry ether
25oC
R – X + Mg R – MgX

Con NaOH
60oC

Grignard reagents are very useful in organic synthesis

Self-Assessment Question(s) (SAQ)

Why are halohydrocarbons polar in nature?

i. Give the product of the react

CH3
H3C – C – CH3
Br

94
 H
CH3 – CH2 – C – CH3
H

Br
Ether
25oC
CuC=C

Self-Assessment Answers

Halohydrocarbons are polar in nature because of the carbon-halogen bond

4.0 Conclusion

The study of Alkyl and aromatic halides have shown the versatility of organic chemistry. In
this unit, you must have learnt new reactions that are applied to the synthesis of organic
compounds. The preparation and reactions of halohydrocarbons are very important and will
be applied henceforth to other preparations.

5.0 Summary

1. The IUPAC nomenclature of halohydrocarbons are similar to alkanes but with some
additional rules.
2. Halohydrocarbons are prepared by the substitution of hydrogen atom.
3. They are classified as primary, secondary and tertiary halohydrocarbons based on the
carbon bearing the halogen atom.
4. Halohydrocarbons are polar in nature and insoluble in water.
5. Halohydrocarbons undergo nucleophilic substitution and elimination reaction.

6.0 Tutor Marked Assignment

1. Outline a procedure for the conversion of methane to propane.

95
2. Outline a synthesis for propan-2-ol starting from propan-1ol
3. What Product(s) would be formed fro the reaction of isobutyl bromide,
(CH3)2CHCH2Br, with each of the following reagents?

7.0 References

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

96
 Unit 11
Hydroxyl Compounds
Contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 Classification of Alcohls
3.2 Iupac Nomenclature of Alcohols.
3.3 Physical and Chemical Properties of Alkanols
4.0 Conclusion
5.0 Summary
6.0 Tutor Marked Assignment
7.0 Reference

97
1.0 Introduction

Hydroxyl compounds are compound which contain OH- groups bonded to a carbon atom and
determine the reactivity of the compound. Compounds containing OH- are called alkanols
(old name alcohol).
In this unit, you will learn the classification of alcohols, IUPAC nomenclature and their
reactivities

2.0 Learning Outcomes

At the end of unit, you should be able to

1. Give the classification of alkonols
2. Give the IUPAC names of alkanols
3. Describe the preparation of primary and secondary alkanols
4. Describe the chemical reactions of alkanols.

3.0 Learning Contents

3.1 Classification of Alcohols

Alcohols may be viewed in two ways: (i) as hydroxyl derivatives of alkanes and (ii) as alkyl
derivatives of water. Alcohols are classified as monohydric, dihydric or polyhydric alcohols
if the compounds contain one, two or more than two OH- group respectively.

C OH Monohydric

C C Dihydric

OH OH

H H H
H C C C H Polyhydric
Monohydric alcohols are further classified as primary, secondary or tertiary when the OH-
OH OH
group is bonded to aOH
primary, secondary or tertiary carbon atom respectively as with
halohydrocarbons.

CH3
H H H H H

H H 98 H3C C CH3
C C OH C C C H

OH
H H H OH H
10 alcohol

Self-Assessment Question(s) (SAQ)

How are alcohol’s classified?
i. Classify the following alcohol given below:
CH3CHOHCH2CH3; CH3C(CH3)(OH)CH2CH3; C(CH3)(OH)
CH3CH2CH2OH; CH2CHCHCH2OH
ii. Write the structural formulas for two alcohol with C4H10O

Self-Assessment Answers

Alcohols are classified as monohydric, dihydric or polyhydric alcohols if the compounds

contain one, two or more than two OH- group respectively.

3.2 IUPAC Nomenclature of Alcohols.

The alcohols are named by charging the ending -e of alkanes to -ol. The IUPAC
nomenclature followed that of alkanes discussed in unit 6. However, the position of the OH-
group is indicated by the number of the carbon bearing the group. And written either before
the parent name or between the parent name and the root.

H CH3
H H H H H
H C C C H H C C C H H3C C CH3

H H OH OH OH OH OH

2-methyl-2-propanol or
Propane- 1-ol Propan- 1,2,3-triol
Isobutanol (common name)
1-propanol

Benzene ring with an -OH+ group is known as phenol

OH

99
Therefore, if a substituent is present on the ring with an OH group. The numbering must start
from the OH bearing carbon atom, as HO the functional group.

OH
Cl Br CH3
OH

2-bromo-6-chloro phenol

C2H5

5-ethyl-2-methyl phenol
Self-Assessment Question(s) (SAQ)
i. Give the IUPAC nomenclature of the following compounds

A. CH3CH2CH2OH
C6H13O
B
C.

OH
CH3
D.

OH

C4H9
E.

3.3 Physical and chemical properties of Alkanols

3.3.1 Physical properties

100
There is the usual graduation in the physical properties of the alcohol as observed in other
homologus series.

The boiling point of the alcohols are usually higher than those of the hydrogen bond that exist
among the molecules of the alcohol compounds. As the number of OH group increase, the
boding point also increase.

H H H H

H C C H H C C H

H OH OH OH

980C
1970C

For the same reason of hydrogen bonding, alcohol are generally soluble in water. However,
solubility in water decrease with increasing length of chain

3.3.2 Chemical Reactions

1. Acidity: Alkanols are very weak acid. They are infact weaker than waqter. (i.e H2O >
ROH). Alkanol can not neutralize aques alkane, they can not lobrate CO2(v) salts.
Phenols can neutralize sodium hydroxide phenol are stronger acid than alkanols i.e ArOH >
H2O > ROH.

2. Reaction with metals

Alkanols and phenols react with metals to librate H2 gas

ROH + Na RONa + H2
CH3OH + Na CH3ONa + H2O
OH ONa

+ Na + H2

Oxidation
Primary alkanol undergoes partial oxidation to give aldehyde and complete oxidation to give
organic acid.

101
 H OH
O O
R CH2OH R C R C
O O

and secondary alkanols undergoes oxidation to give ketones

H
O
[O]
R C OH R C
R
OH
While tertiary alkanols are resistance to oxidation. Oxidizing agents usually used for these
purpose include
Acidified KMnO4 which changes from purple to colour and
Acidified K2Cr2O7 which changes orange to green.

CH3 Acid KMnO4 CH3

H3C C C H3C C

OH O

4. Substitute reaction

This involves the replacement of the OH group by other atom or group atoms. Phenol do not
undergo this reaction.

ROH + PCl5 R- Cl + HCl + POCl3

3R- OH + PCl3 3R-Cl + H3PO3
R- OH + SOCl2 R- Cl + SO2 +HCl
R- OH + HCl ZnCl2 R- Cl + H2O
Reflux

NaBr/H2SO4
R- OH + HBr Reflux R-Br + H2O

5. Elimination Reaction
Alkanols undergo elimination reaction to remove one molecule water concentration H2SO4 at
about 1700C is used as reagent. Phenols do not undergo elimination reactions.

H H
H
H
H Con H2SO4 H + H2O
H C C C C
heat
H H
H OH

102
6. Esterification Reaction

This is the reaction between an organic acid and an Alkanol to produce ester and water. The
reaction is reversible and it is catalyzed by mineral acid e.g H2SO4

H O O
+ H2O
H C C + H2SO4 C C
CH3OH
O CH3
OH
H

6. Lucas Test:
This test is used to distinguish between 10, 20 and 30 ROHs.

The reagent used is a mixture of HCl/ZnCl2 solution.

R – OH + HCl ZnCl2 RCl + HCl + H2O

Observations: the reaction formed a two layers that are insoluble;

With 30 ROH, the reaction is instantly at room temperature

With 20 ROH, the reaction takes a layer time at room temperature
With a 10 ROH, heating is required for the reaction to go on.

These observations helps to differentiate the three classes of alkanols (i.e the energy
requirement and duration of reaction).

6. Iodo form Test

This test is used in elucidating the structure of the alkanol involved. The reagent used is a
solution of iodine in sodium hydroxide solution. (I2/NaOH). A positive iodine test gives a
yellow precipitate test (to CHI3). A positive test confirm the presence of the group.

CH3 – CH – R in the ROH

OH O
CH3 – CH – C2H5 I2/NaOH CHI3 + C – C2H5
HO
OH

Self-Assessment Question(s) (SAQ)

103
What is esterification?
i. Give the product and their IUPAC name of the following reactions
OH

Heat
Con. H2SO4

b.
CH3CHCOH NaBr/H2SO4
Reflux
CH3

CH3

c acid KMnO4
H3C C CH

CH3
ii. Give the structural of the alkanol with molecular formula C4H9O which react instantly
with HCl in the presence of ZnCl2 as catalyst.

Self-Assessment Answers

This is the reaction between an organic acid and an Alkanol to produce ester and water.

4.0 Conclusion

In this unit, you must have learnt about the classification of alkanols, their IUPAC naming,
physical properties and chemical reactivities. Knowledge of these items will be very useful in
the study of organic chemistry.

5.0 Summary

1. Alkanols are classified as monohydric, dihydric or polyhydric on the number of OH

group contained in the molecule.

104
 2. Monohydric Alkanols are classified as 10, 20, or 30 alkanols depending on the type of
carbon atom that bears the OH group
3. Alkanols are named by changing the ending in corresponding alkane to –ol with a
number indicating the position of the group on the carbon chain
4. Alkanols are polar, the boiling point is higher than its making soluble in water. The
boiling point is higher than its counterpart hydrocarbon or halohydrocarbon.
5. Alkanols undergo variety of reactions which make them useful in organic synthesis.

6.0 Tutor – Marked Assignment.

1. Identify the following monohydric alkanol

a. (CH3)3CCH2CH2OH
b. CH3CH(CH3)CH(OH)CH3
c. CH3C(CH3)CH3

OH
d.

OH
2 Starting with each of the following outline a practical synthesis of 1-butanol.
a. 1- butane
b. 1- Chlorobutane
c. 2-Chlorobutane

3 Show how you might prepare 2-bromobutane from 1-butanol

4 Give the structural and names for the compounds formed when 2-butanol is treated
with
a. Sulfuric acid at 1400C
b. Refluxing concentration HBr

7.0 Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

105
 Unit 12
Carbonyl Compounds
Contents

1.0 Introduction
2.0 Learning Outcomes
3.0 Learning Contents
3.1 General Classification
3.2 Iupac Nomenclature
3.3 Preparations
3.4 Physical And Chemical Properties
4.0 Conclusion
5.0 Summary
6.0 Tutor Marked Assignment
7.0 Recommended Books

106
1.0 Introduction

CarbonyI compounds are those organic compounds that contains a carbon atom with a double
O
bond to oxygen ( - c - ). These compounds are grouped into two. The Aldehydes and the
ketones. In this unit, you will learn about their IUPAC nomenclature, preparation and
chemical reaction which are very useful in the planning of organic systhesis.

2.0 Learning Contents

At the end of this unit, you should be able to

1. Differentiate between aldehydes and ketones
2. Describe their preparations
3. Give their IUPAC nomenclature
4. Discuss their chemical properties.

3.0 Learning Contents

3.1 General Classification

Compounds contains carbonyl group as the functional group are divided into two, the
Alkanals (Aldehydes) and the Alkanones (Ketones)
In the Alkanals, the carbonyI group is at the terminal end and is bonded to an hydrogen atom.

C H
R

While in the Alkanones, the carbonyI group is bonded between two alkyI groups (i.e between
two carbon atoms)
O

R C R’

107
 The first three members of the Alkanals are:

O O O

C H CH3 C H CH3 CH2 C H

H

Methanal Ethanal Propanal

While the simple member of the Alkanone is

CH3 C CH3

Propanone

Both groups are isomers and exhibit some similarities in their chemical reaction. Alkanals
and Alkanones have a trigonal planar arrangement of groups around the carbonyI carbon
atom.

The carbonyI carbonyI atom is 5p2 hybridized.

Self-Assessment Question(s) (SAQ)

1. Give the general formulas for Alkanals and Alkanones.

3.2 Iupac Nomenclature

In the IUPAC system, aliphatic alkanals are named by replacing the final –e of the name of
the corresponding alkane with –al. since the Alkanal group must be at the end of the chain of
carbon atoms, there is no need to indicate its position. When other substituent are present, the
carbonyI carbon is assigned position 1.

H H H H H CH3 C
O O
H
H C C C C H C C C C

H CH3 H H H H H
108
2- butenal Pheny I ethanol
3 – Methy I butanal
(but-2-enal)
When a carbonI group is attached to a ring system, the suffix carbaldehyde is added to the
name for example.

O
C H O

Benezene Carbaldehyde Cyclohexane Carbaldehyde

(benezaldehyde

Alphatic Alkanone are named subtitutley by replacing the ending –e of the name of the
corresponding alkane with – none.
The chain is then number in such a way that gives the carbonyl carbon atom the lower
number possible. The position of the carbonyI carbon is indicated in the name.

O O O

CH3 CH2 C CH3 CH3 CH2 CH2 CH3 C CH2 CH = CH2

C C H3
butanone H Pentan -2- one
(2- pentanone)

Self-Assessment Question(s) (SAQ)

i. Give the IUPAC named for the isomeric aldehydes and ketones with the formula
C5H100

3.3 Preparations

3.3.1 ALKANALS
Alkanals are prepared by the following methods:
Oxidation of primary Alcohols

O 109
R–C-H
H
 H
[ 0]
R–C-H
OH

Reduction of an organic acid derivatives

O
R [H] or L1AIH3
3.3.2 Alkanones
C R C

Cl H

Ketones can be produced the following methods:

Ozonolysis of alkenes will give aldehyde and ketone depending on the starting material.

R
R R R
R
C=C
C=0 +0=C
O3, Zn H20
R H H
R H
Oxidation of secondary alcohol

OH O
KMn04
R C R R C R

Reaction of nitile (R- C=N) with a Grignard reagent or an organolithium reagent and then the
product is hydrolysed to give ketone.

N- mg x + O
R – C = N + R – Mg x R C H20 R C + NH4 x + Mg x
R
R

N- L1 + O
R – C = N + R – LI R C H20 R C + NH4 + LI+

0 R
Reaction of Acylchloride with a solution of
R lithium dialkylcuprate low temperature (-78 c)

O O

R2 Cu LI + R – C R C + Rcu + LI + CI
CI R
110
Self-Assessment Question(s) (SAQ)
i. Using equation, give the synthesis of
a. 4 – methyI pentan -2- one
b. 3 –methyI butanal

Self-Assessment Answers

3.4 Physical and Chemical Properties

3.4.1 Physical Properties

The carbonyI groups are a polar in nature, therefore, the boiling point of the aldehydes and
ketones are higher compared to hydrocarbons of the same moelecular weight but lower to
those of alcohols. These is because the hydrogen bond present in them are not as strong as
those in alcohols. The lower bond present
The following compounds have the same molecular weight but their boiling point defers
O O
CH3CH2CH2CH3 CH3CH2CH CH3CCH3 CH3CH2CH2OH
0.50C 490C 560C 97.20C

3.4.2 Chemical Reactions

1. Nucleophilic Addition to the carbon – oxygen double bond.’

OH O

R C H H – Nu R C OH

With ROR

OH OR
ROR
R H R C R
C
OH H OCH3
CH3 OCH3
C H3 H CH3 C CH3
C
111
H
With H - = N

O OCN
H - CN
C H3 H CH3 C OH
C

With NaHSO3

O ONa
NaHSO3 OSO2H
C H3 H CH3 C
C

This reaction is used to separate carbonyI compound from a mixture. Because the original
carbonyI compound can be regenerated by acidifying the product which is a colourless
crystal.

2, Addition reaction with Grignard reagent

Methanol react with Grignard reagent to give 10 alcohol, higher alkanal react to give 20
alcohol while ketones react to give 30 alcohol.

O Mgx OH
O
H20
H C H + Rmg x H C R H C
O Mgx OH
O
H H20 H
R C H + Rmg x R C R R C R

H H
3. Addition of derivatives of Ammonia
The reaction with the derivatives of ammonia may be represented by the general formula.
H2N – Z, where Z may be anything
e.g Hydroxylamme, H2N – OH (Z = OH)
Hydrazine H2N – NH2 (Z = NH2)

112
2,4- dinitrophenyI hydrazine, H2N – N02 (2,4 – DNP)

NO2
R R
Reaction :
C = 0 + H2N – Z C = N – Z + H2O
R R

The reaction of carbonyI with 2,4 – DNP gives a yellow precipitate.

This reaction is used in the identification of alkanals and ketones.

4. Reduction Reaction
The reduction of carbonyI gives an alcohol. Aldehydes are reduced to 10 alcohols while
ketones are reduced to 20 alcohols. The reduction reaction can be carried out using
 H2 gas in the presence of a Nickel catalyst
 LIAIH4 (Lithium tetrahydrido aluminate III
 NaBH/4/MeOH (Sodium tetrahydridoborate III)
OH

L1AlH4
CH3 C CH3 C – H
H
H

O OH

NaBH4
CH3 C CH3 CH3- C - H

CH3

3.4.3 Differences between Alkanals and Alkanones

The Alkanal group show reducing properties, as a result of these undergo oxidation with
some mild reagents.
1. Fehling Test
Fehling solution is an alkaline solution of CuS04 (deep blue). So Alkanal reduces fehling
solution to give a red precipitate.

O O

R–C + Cu2+ R–C + Cu2O (red)

H
O (-)
113
2. Tollens Test (Silver Mirror Test)
The ease with which aldehyde undergo oxidation provides a useful test that differentiate
aldehydes from ketones. A mixture of aqueous silver nitrate with aqueous ammonia produces
a solution known as Tollens’ reagent.
Alkanals reacts with the reagent to give a deposit of silver which appears as a shining mirror
with ketones, there is no reaction.

3. Oxidation using KMn04 or K2 Cr2 07

Alkanal undergo oxidation to give organic acid and decolourize KMn04 from purple to
colourless or K2 Cr2 07 from orange to green. While ketones do not undergo oxidation
reaction.

4. Iodoform Test
As in unit 11, a positive reaction or test gives a yellow precipitate indicating the presence of a
CH3 – alkyI group.

O O
I2/NaOH
CH3 C CI3 + I - C
R R

Self-Assessment Question(s) (SAQ)

i. Starting with ethanol, outline the synthesis of butan – 2 - 01
ii. Outline simple chemical test to distinguish between
i. Hexanol and 2-hexanone
ii 2- Hexanol and 2- Hexanone.

4.0 Conclusion

The reaction of the carbonyI groups are very interesting to learn. This unit have introduced to
you. The naming of the carbonyI groups, their preparation and chemical properties which are

114
utilized the synthesizing other organic products. A good knowledge of the carbonyI is
necessary for the understanding of organic synthesis.

5.0 Summary
1. carbonyI compounds are classified into two groups namely Alkanals (aldehydes)
and Alkanones (ketones) with the general formulas R – C – H and R – C – R
respectively.
2. Alkanals are name by replacing the ending –e in the corresponding alkane to al
while for Alkanone is – one
3. Aldehydes and ketones can be synthesized in the laboratory by various methods
including oxidation of 10 and 20 alkanols.
4. Lower members of the carbonyI compounds are soluble in water due to the presence
of hydrogen bonds which increased the boiling point of all members of the
carbonyls.
carbonyI undergo reactions in similar fashion to give different products.
5. The aldehydes are reducing in nature which help to differentiate them from the
ketones. Using fehling reagent and Tollens’ reagent.

6.0 Tutor – Marked Assignment

1. Write the structural formula for the products formed when propanal reacts with
following reagents.
i. NaBH4 in aqueous NaOH
ii. LIAIH4 then H20
iii. C6H5 Mg Br then H20
2. Give the structure of the compound A – E from the reaction below:
H CrO CH MgI H2SO4
Cyclohexanolacetone
2 2
A(C6H10O) H O3 B(C7H14O) C(C7H12)
2 heat
O3 Ag2O,OH
Zn,HOAr D(C7H12O2) H2 O
E(C7H12O3)

3. Give the structure of A, D, if compound A and D do not give a positive tollens’ test
but compound C does.
Mg,
4-BromobutanalHOCH
HA
2CH2OH A(C6H12O2Br) Et2O
[B(C6H12MgO2Br)]
CH3CHO CH3OH,
H3O+,H2O C(C6H12O2) H2SO4 D(C7H14O2)

Recommended Books

115
Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

116
 Unit 13
Organic Acids
Contents

1.0 Introduction
3.0 Learning Outcomes
3.0 Learning Contents
3.1 Nomenclature of Carboxyl Acids.
3.2. Preparation
3.3 Properties of Carboxylic Acid
4.0 Conclusion
5.0 Summary
6.0 Tutor Marked Assignment
7.0 Recommended Books

117
1.0 Introduction

Organic acids contain the carboxyl group as their function groups the carboxyl group contain
both the carboxyl and hydroxyl group However, the reactions of the carboxyl group are
different from those of these other two groups as individual.

O
The carboxyl group (-COH is one of the most widely occurring functional group in chemistry
and biochemistry. Not only are carboxylic acid important, it is the parent group of a large
family of related compounds called acyl compounds.

In this unit, you will learn the IUPAC nomenclature, their preparation and the basic reaction
as an introduction to future study in organic chemistry.

2.0 Learning Outcomes

At the end of this unit, you should be able to
1. name any carboxylic compounds
2. describe the preparation of simply carboxylic compound
3. discuss the chemical properties of carboxylic groups.

3.0 Learning Contents

3.1 Nomenclature of Carboxyl Acids.

The IUPAC systematic names for carboxyl acids are obtained by replacing the ending –e of
the corresponding alkane of the longest chain identified in the acid, to –oic acid. The
carboxyl carbon atom is assigned number 1. For example:
O O
CH3 CH2 CHCH2 COH CH3 CH = CH2 CH2 COH
CH3 4-methylhexanoic acid 4-Hexenoic acid (Hex-4-enoic acid)

Methanoic acid is the lower and simplest member of the group followed by the ethsnoic acid.
Methanoic acid is sometimes referred to as acetic acid.

The salts of carboxylic acids are named as –ates; -ate replaces –ic acid. Thus CH3 CO2 Na is
known as Soduim ethanaote.. The chain with the carboxylic group forms the parent chain and
hence the root of the name.

118
O O O
 H3C – C H3C – C H3C – C
O – CH3 O – C3H7 O – C6Hs

Methylethanoate Propylethanoate Phenylethanaote

Salts of carboxylic acid with alkyl group attached to the oxygen atom as in the above
examples are referred to as ester group.

Self-Assessment Question(s) (SAQ)

What are ester groups?

.
Give the structural formulas of the following
a. Methyl propanoate
b. Ethyl p- nitrobenzoate.
ii. Give the IUPAC names of the following
a. CH3 CH2CHCO2H
CH3
b. C6H5CH2CH2CH2CO2H
c. CH3CH = CCH2CO2H
CH3

Self-Assessment Answers

Salts of carboxylic acid with alkyl group attached to the oxygen atom as in the above
examples are referred to as ester group.

3.2. Preparation

Most of the method for the preparation of carboxyl acid have been discuss in earlier units; but
for the sake of emphasis

i. By Oxidation of alkene (under alkenes)

KMnO4
R – CH = CHR’ RCO2H + R’CO2H
H3O
R- CH =CHR’ O 3 RCO2 H + R ‘CO2 H
H2O2
ii. By Oxidation of Aldehydes and 10 akohols
Ag2O
H3 O+
119
 R – CHO RCO2 H
-
RCH2OH KMnO4 OH RCO2 H
H3O+
iii. By Oxidation of alkylbenzenes
KMnO4, OH- CO2H
CH3
H3O+

4. By hydrolysis of cyanohydrins and other nitriles

R
OH
R
C=O HCN C OH HA
RC – CO2H
R R CN H2O

R – CH2X NaCN R – CH2 RCH2

80% CN CO2H

Self-Assessment Question(s) (SAQ)

i. Show how the following compounds could be converted to benzoic acid
a. Ethyl benzene c. Phenylethene.
b. Benzyl alcohol

3.3 Properties of Carboxylic Acid

3.3.1 Physical Properties

Carbonxyl acids are polar compounds, therefore their molecules form strong hydrogen bonds
with each other and with water molecules As a result, they have high boiling point and low
molecular weight carboxyl acid are readily soluble in water.

Carboxyl acids react readily with sodium hydroxide and sodium bicarbonate to form soluble
salt of sodium. Though they are weak acid, they are stronger than phenols and alkanols

3.3.2 Chemical Reactions

1. Reaction with metals it react to displace H2 gas

2CH3 COOH (CH3 COO)2 Mg + H2
Mg

2. Substitution Reaction of carboxylic acid

120
 a. Replacement of the OH group
RCOOH + PCl5 RCOCL + POCL3 + HCL
b. Replacement of hydrogen atoms on C-2 (alpha carbon atom)
CH3 CH2 COOH Br2, P CH3 CH COOH CH3 C(Br)2 COOH
Br
0
3. Carboxylic acids are reduced to form 1 alcohols.
RCOOH LiA1H4 R.CH2OH
ether
4. Decarboxylation – Carboxylic acid and their salts lose CO2 on strong heat with soda
lime
RCOOH Soda lime RH + CO2
heat
5. Etherification - Carboxylic acids reacts with alcohols to form esters through a
condensation reaction known as esterification. This reaction is a reversible one, therefore the
hydrolysis of ester give alcohol and acid.

Strong acid
R – C – OH + R’-OH R – C – O – R’ + H2O
Acid
O alcohol ester
O

Self-Assessment Question(s) (SAQ)

i. Give the products of reactions of propanoic acid with
a. Calcium
b. PCL5
c. LiAIH/ether
d. CH3 CH2 CHOHCH3

ii. Identify A-C and give their possible structures.

A (C4 H10 O H+/Cr.2, O7 2+ B(C4H8O) H+/kMnO4 C (C4H8O2

Ag/NH3 Silver mirror

Self-Assessment Answers

121
4.0 Conclusion

This unit have been able to introduce the naming preparations and reactions of carboxylic
acid to you. This basic knowledge will be required in advance organic chemistry topics in the
future

5.0 Summary

1. Carboxyl acids are organic acids with a wide application in chemistry and
biochemistry.
2. They are named by replacing the ending –e in alkane to oic acid.
3. They can be prepared by the oxidation of other organic compounds.
4. Their reaction are much with wide industrial application which include esterification,
reduction reaction etc.

6.0 Tutor Marked Assignment

1. Give the IUPAC names of the followings:-

a. H2C=CHCH2COOH
C3H7

b. CH2CH2CH2COOH

CH3
c. CH3CHCHCOOH
Br
d. CH3C O
O – CH2CH2CH3
O
e. CH3C
O

2. Outline the synthesis of butanoic acid start from ethane

3. Give the products of the reactions below

a. CH3CHC O liAlH4
CH3 OH ether

O Br2
122
 b. CH3CHC
OH
CH3

7.0 Reference

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

123
 Unit 14
Derivative of Carboxylic
Acid and Other
1.0 Introduction
2.0 Learning Outcomes
3.0 learning Contents
3.1 Ethers
3.2 Ester
3.3 Amines
4.0 Conclusion
5.0 Summary
6.0 Tutor-Marked Assignment
7.0 Reference

124
1.0 Introduction

This group of organic compounds comprises ethers, Amines ester and Amide. They are
important homologues group that are derivatives of others already studied. Their application
to every day chemistry makes their study important.
In this unit, you will only be learning their nomenclature, and general properties.

2.0 Learning outcomes

At the end of this unit, you should be able to

1. Identify ether, ester, amine and amide
2. Give the IUPAC names of any compound of the above mentioned groups.
3. List the properties of each group mentioned above

3.0 Learning Contents

3.1 Ethers

Ethers have the general formula R-O-R or R-O-R’ where R may be an alky or phenyl group.
Ether can be thought of as water derivatives in which both hydrogen atoms have been
replaced by alkyl groups.
Ethers can be prepared by

1. the intermolecular dehydration of Alcohols.

R – OH + HO – R H2SO4 R–O–R
140oC
2. Nucleophilic substitution reaction of sodium alkoxide with alkyl halide, alkyl
sulfonate or alkyl sulfate.

R –O-Na+ + R+ - X R – O – R’ + NaX

125
Ether are named by identifying the two alkyl group bonded to the oxygen atom. The RO-
group is called the alkoxy group and it name forms the prefix while the R- group forms the
root, for example

CH3CH2CH2 – O – CH2 – CH3 CH3 CHCH2CH2CH3

propoxyethane OCH3

C2H5O CH3OCH2CH2CHOCH3
CH3
1 – ethoxy – 4 – methylbenzene 1,2-dimethoxyethane

Ethers are able to form hydrogen bond with water molecules so they are soluble in water.
Ethers react with very few reagent other than acids. They generally resist attack by
nucleophiles and bases, just like alkanes ether can only undergo substitution reactions with
halogens
R – O – CH3 + HBr R – O CH2

Self-Assessment Question(s) (SAQ)

i. Give the names of the following ethers
a. CH3CH2CH – O CH3
CH3
C 3 H7
b. CH3CH2C – O – C3H7

ii. Give the names of the products of the reactions below

a. CH3CH2CH – CH – ONa + C2H5Br
C2H5
b. CH3CH2C – O – CH3 HBr

C2H5

Self-Assessment Answers

126
3.2 Ester
We have discussed the naming of ester and its synthesis in unit 12. however, it is important to
note one or two properties about esters. Estes are formed by the condensation reaction of
organic acid and alcohol. Esters are named as derivatives organic acids. Their names end with
the –oate while the alkyl from the alcohol group is named first for example.

O O
CH3C O CH3CH2C – O Cl
C – O – CH3
O – C3H7

Propylethanoate phenyl propanoate methyl-p-chlorobenzoate

Esters are polar group but lack hydrogen bonding among the molecules therefore, exhibit low
O
boiling [Link] have pleasant odour, some resembling those of fruits and are therefore
used in the manufacture of synthetic flavor. Because esters are non-reactive of, they used to
create inert environment for very reactive species.
Self-Assessment Question(s) (SAQ)
1. Give the IUPAC names of the following

a. CH3C O
O – C2OH5
b. CH3CH2CH2C
O– CH3

2. Give an outline for the synthesis of a named ester.

3. State one important use of ester

Self-Assessment Answers

3.3 Amines

Amines are regarded as organic derivatives of NH3 in which are one or more of the hydrogen
atom have been replaced by alkyl groups. Amines are organic bases with functional group of
–NH2. They are classified as 1o, 2o or 3o amine based on the number of alkyl group attached
to the functional group.
127
 H
R – N – H 1+ amine
R
R–N–H 2o amine
R
R – N – R 3o amine

Amines are named as amino alkane of the R group present when there are two or more R-
group, the one with the longest chain of carbon atom is used as the parent name while others
are regarded as substituents on the N-atom.

H H H H C2H5
H C C C N H3CCH2 – N – CH3 H3C7 – N – CH3
H H H H H
Amino propane N-methylaminoethane N-ethyl-N-methyl
aminopropane

C3H7 – N – CH3 N,N-Dimethylpropane

For Arylamines (i.e. aromatic ring attached to amines)
NH2
NH2
NH2CH3

OCH3
Benzenamine N-methylbenzenamine 4-methoxybenzenamine

Amine are prepared through nucleophilic substitution reaction

Self-Assessment Question(s) (SAQ)

1. GIVE the IUPAC names of the follow structures

128
 NH2
a.

CH3
C2H5
b. CH3NCH3
C2H5
c. CH3NC2H5

d.
H3C
NC2H5
H

2. Arrange these compounds in the other of increasing acidity

CH3CH2C O ; CH3C O ; C6H5OH; C3H7OH,

O O
C3H7NHCH3

Self-Assessment Answers

4.0 Conclusion

In this unit, you have been introduced to the basics of important organic and bioorganic
compounds. Their nomenclature and basic properties. This is just a step towards
understanding more complex organic structures still ahead.

5.0 Summary

129
1. Ether are polar organic compound prepared by dehydrogenation of alcohols and
nucleophilic substitution of sodium alkoxide.
2. Esters are products of condensation reaction of carboxylic acids and alcohols. They
are inert and have sweet smells.
3. Amine are regarded as ammonia derivatives prepared by nucleophilic substitution
reaction.

6.0 Tutor Marked Assignment

1. Give the name of the following compounds:
O O
a. CH3CH3CCH2CH2CH2C – CH3

b. CH2

O – C2H5
c. C6H5 – C O
O – C2H5
d. C3H7 – N – CH3
CH3
2. Outline the preparation of a named ether

O
3. Outline the synthesis of CH3CH2C

O – C2H5

7.0 Recommended Books

Solomon G. and Fryhle C. 2000. Organic Chemistry. John Wiley & Sons. Inc. New York.

Carret R., Denniston K. And Topping J. 1997. Principles and Applications of Inorganic,
Organic and Biological Chemistry. McGraw Hill. New York.

Daintith J. 2008. Oxford Dictionary of Chemistry, 6th edition. Oxford University Press. New
York.

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