Chapter 7 – Organic Chemistry

You must be able to:

Uniqueness of Carbon

Describe organic molecules as molecules containing carbon atoms with the

exception of carbon dioxide, carbon monoxide, diamond, graphite,
carbonates (or bicarbonates), carbides and cyanides
State that carbon has a valency of four in a tetrahedral arrangement
Carbon atoms can form single, double or triple bonds
State that carbon forms strong covalent bonds with itself and many other
elements
Describe carbon as the basic building block of organic compounds that
recycles through the earth‘s air, water, soil, and living organisms

Organic Molecular Structures – Functional Groups, Saturated and

Unsaturated Structures; Isomers

Define
a functional group as an atom or a group of atoms that form the
centre of chemical activity in the molecule
a hydrocarbon as a compound containing only carbon and hydrogen
atoms
a homologous series as a series of similar compounds which have
the same functional group and have the same general formula, in which
each member differs from the previous one by a single CH2 unit
a saturated compound as a compound in which all of the bonds
between carbon atoms are single bonds
an unsaturated compound as a compound in which there is at least
one double and/or triple bond between carbon atoms
Identify compounds that are hydrocarbons
Identify compounds that are saturated and unsaturated
Identify the functional group of compounds belonging to the following
homologous series: Alkanes, Alkenes, Haloalkanes (Alkyl halides), Alcohols,
Carboxylic acids, Esters

IUPAC Naming and Formulae; Isomers

Write the IUPAC name when given the formula of compounds in the
homologous series: alkanes, alkenes, haloalkanes, alcohols,
carboxylic acids and esters (up to 8 carbon atoms)

Compiled by St John’s College Science Department, adapted by Beaulieu College Science Department

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NOTE the following for naming purposes:
 Naming and drawing of organic compounds is restricted to one type of
functional group per compound and to a maximum of two functional groups
of the same type per compound, except for haloalkanes, where a maximum
of two different halogen substituents (e.g. bromo- and chloro-) are allowed
per molecule
 The only substituent chains that are allowed in naming and reactions are:
methyl- and ethyl- groups
 A maximum of THREE substituent chains (alkyl substituents) are allowed on
the alkane, alkene, haloalkane, alcohol or carboxylic acid parent chain
 When naming haloalkanes, the halogen atoms do not get preference over
alkyl groups – numbering should start from the end nearest to the first
substituent, either the alkyl group or the halogen. In haloalkanes where e.g.
a Br and a Cℓ have the same number when numbered from different ends of
a chain, Br gets alphabetic preference
 When writing IUPAC names, substituents appear as prefixes written in
alphabetically (bromo, chloro, ethyl, methyl), ignoring the prefixes di- and tri-
 When writing IUPAC names, the following conventions must be followed:
o Numbers are separated from letters using a dash (-)
o Numbers areseparated from numbers using a comma (,)
o Letters are not separated at all (i.e. no space is used), with
the exeptions being esters (e.g. methyl ethanoate) and
carboxylic acids (i.e. propanoic acid)
 Although in some smaller molecules numbering becomes redundant,
redundancy will not be penalised. For example methylbut-2-ene may be
written as 2-methylbut-2-ene without penalty. The only exeption is if
numbering is always redundant, e.g. for a carboxylic acid: butan-1-oic acid
will be penalised, as it must be written as butanoic acid
 For euphonic purposes, the vowel “e” is generally removed from the name
before the suffix, e.g. butan-i-ol instead of butane-1-ol. However this is not
done for diols, e.g. butane -1,2-diol is correct and not butan-1,2-diol
 For euphonic purposes, the vowel “a” must be added to the name before the
suffix for dienes, e.g. buta-1,3-diene is correct, and not but-1,3-diene

Write down, identify and apply the general formula for alcanes (CnH2n+2) and
alkenes (CnH2n). Note: Only one double bond will be considered when
assessing general formulae

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 Draw structural, condensed structural and molecular formulae for
compounds belonging to the following homologeous series: alkanes,
alkenes, haloalkanes, alcohols, carboxylic acids and esters (up to 8 carbon
atoms)

Examples of different types of formulae for ethanoic acid

Structural Condensed structural Molecular

Atoms are represented by The way in which atoms This is a chemical formula
their chemical symbols are bonded but NOT ALL that indicates the type of
and lines are used to bond lines are shown atoms and the correct
represent ALL bonds number of each in the
between atoms molecule

Define structural isomers as compounds having the same molecular

formula but different structural formulae
Identify compounds that are structural isomers (up to 8 carbon atoms).
Structural isomers are restricted to:
o Chain isomers
o Positional isomers
o Functional isomers
NOTE: No cis-, trans or stereo-isomerism will be assessed

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Examples of types of structural isomerism

Type of isomer Description Example

Chain isomer Different type of chain butane and methylpropane
structure, i.e.
branching
Positional isomers Different positions of i) 1-chloropropane and
the same functional 2-chloropropane
group on the parent ii) but-1- ene and but-2-ene
chain iii) ethyl methanoate and
methyl ethanoate
Funtional isomers Different functional propanoic acid and ethyl
groups methanoate

Relationship between Physical Properties and Structure

Recognize and explain the relationship between melting point, boiling point,
and the strength of the intermolecular forces as influenced by
Number and type of functional groups
Chain length
Branched chains
(See the intermolecular forces section)

Organic Chemical Reactions (ONLY alkanes, alkenes, haloalkanes, alcohols,

carboxylic acids and esters)

Know that many organic compounds are flammable and suggest a suitable
method of heating organic liquids
Classify and identify the following GENERAL reaction types: combustion
(oxidation), substitution, addition, elimination and condensation
(esterification)

a) Combustion Reactions

State that combustion reactions are exothermic and hence explain the
importance of fossil fuels in terms of their ability to transfer chemical
potential energy into heat energy
Write balanced chemical equations to represent the complete combustion of
alkanes, alkenes and alcohols with excess oxygen to produce water and
carbon dioxide

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b) Substitution Reactions

When given the appropriate reaction conditions, write balanced equations to

show the formation of substitution products in the following SPECIFIC types
of substitution reactions:
Halogenation (free radical halogenation): alkanes to haloalkanes
 eg. CH4 + Cℓ2  CH3Cℓ + HCℓ
 Reaction condition: in the presence of ultraviolet light or heat
Hydrolysis: haloalkanes to alcohols

 Eg. CH3Cℓ + NaOH(aq)  CH3OH + NaCℓ

 Reaction conditions: heat under reflux in a dilute alkali solution
c) Addition Reactions

When given the appropriate reaction conditions write balanced equations to

show the formation of addition products in the following SPECIFIC types of
addition reactions:
Hydrogenation: Addition of H2 to any alkene
 Eg. CH2 = CH2 + H2  CH3 – CH3
 Reaction condition: alkene dissolved in an organic solvent with a
catalyst (Pt, Pd, Ni) in a H2 atmosphere
Halogenation: Addition of X2 (X = Cℓ, Br)
 Eg. CH2 = CH2 + Cℓ2  CH2Cℓ-CH2Cℓ
 Note: Rapid decoulirisation of bromine water by an alkene at room
temperature is used to distinguish an alkene from an alkane
(test for unsaturation)
Hydrohalogenation: Addition of HX to any alkene
 Eg. CH2 = CH2 + HCℓ  CH3 – CH2Cℓ
 Reaction condition: no water may be present
Hydration: Addition of H2O to any alkene
 Eg. CH2 = CH2 + H2O  CH3 – CH2OH
 Reaction condition: steam and a suitable catalyst eg H3PO4
When two addition products are possible, either will be accepted

d) Elimination Reactions

When given the appropriate reaction conditions write balanced equations to

show the formation of elimination products in the following SPECIFIC types
of elimination reactions:
Dehydrohalogenation: Elimination of HX from any haloalkane
 e.g. CH2Cℓ-CH2Cℓ  CH2 = CHCℓ + HCℓ

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  Reaction condition: hot concentrated NaOH or KOH in an ethanol
solvent i.e. in the absence of water

Dehydration of alcohols: Elimination of H2O from any alcohol

 e.g. CH3 – CH2OH  CH2 = CH2 + H2O
 Reaction condition: acid catalyzed dehydration – heating of alcohol
with an excess of H2SO4 or H3PO4
Cracking of hydrocarbons: Breaking up of large hydrocarbon molecules into
smaller and more useful molecules, specifically a smaller hydrocarbon and
one or more small alkenes
 Reaction conditions:
 thermal cracking - high pressures and temperatures without a
catalyst
 catalytic cracking – lower temperatures and pressures in the
presence of a catalyst
When two elimination products are possible, either will be accepted

e) Condensation or Esterification Reactions

State or identify the appropriate reaction conditions and write balanced

equations to show the formation of esters
State that an acid catalyzed condensation reaction between an alcohol and a
carboxylic acid produces an ester and water
Identify the alcohol and carboxylic acid used to prepare any given ester
Given any alcohol and carboxylic acid, identify the ester produced
Write an equation to represent the preparation of an ester

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1. Introduction
This is the study of the compounds of carbon excluding CO2, CO, diamond,
graphite, carbonates, carbides and cyanides which are regarded as inorganic.

Organic molecules can range in size from simple molecules to complex structures
containing thousands of atoms.

Carbon compounds are found in:

FOODS : proteins, fats, starches and vitamins.

CLOTHING : wool, cotton, silk, nylon.

PACKAGING : wood, cardboard, paper, cellophane.

FUELS : petrol, diesel, paraffin.

PLASTICS : polystyrene, perspex, teflon.

ALL LIVING ORGANISMS:

2. Uniqueness of Carbon
Carbon is unique from the other elements in 3 ways

a) Carbon is unique in that it forms strong carbon to carbon bonds and permits
long chains to form. This property is called catenation - the bonding of
atoms of the same element into longer chains.

b) Carbon forms predominantly covalent bonds with itself and other elements
such as hydrogen, oxygen, sulphur and nitrogen. These bonds are polar
covalent.

c) All four valence electrons in the carbon atom are available for bonding.
Carbon atoms can form single, double or triple bonds.

Compiled by St John’s College Science Department, adapted by Beaulieu College Science Department

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3. Sources of Carbon & Carbon Compounds
a) The chief source of carbon in living organisms is carbon dioxide CO 2.
Carbohydrates are produced by photosynthesis.

6CO2 + 6H2O  C6H12O6 + 6O2 H > 0

b) Oil and coal and natural gas. These natural resources can be used to
synthesise a wide range of products. e.g. plastics, glues, drugs, etc.

c) Carbon is the basic building block of organic compounds. Carbon recycles

through the Earth’s air, water soil and living organisms.

4. Organic Formulae
a) Molecular Formula

This form is a chemical formula that indicates the type of atoms and the
correct number of each atom in the molecule

e.g. C2H4O2 ethanoic acid

b) Empirical Formula

This formula indicates the simplest ratio of atoms of each element to one
another.

e.g. CH2O ethanoic acid

c) Condensed Structural (Semi-Structural) Formula

This formula shows the way in which the atoms are bonded but not all the
bonding lines are shown

e.g. CH3COOH, ethanoic acid

Compiled by St John’s College Science Department, adapted by Beaulieu College Science Department

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d) Structural Formula (Displayed Formula)

The atoms are represented by their chemical symbols and lines are used to
represent all the bonds between atoms

It should be noticed that:

i) each carbon atom forms 4 bonds with other atoms;
ii) oxygen forms 2 bonds with other atoms;
iii) hydrogen atoms form 1 bond with another atom
iv) halogens form 1 bond with other atoms.

Exercise 1
Draw the structural formula for:

a) C2H5Cl

b) CH2OHCH2CH3

Compiled by St John’s College Science Department, adapted by Beaulieu College Science Department

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 5. Hydrocarbons (compounds containing
only H and C atoms):
Hydrocarbons

Aliphatic Aromatic
cyclo-aliphatic (Contains Benzene rings)
(Includes all ring structures except Benzene) H
H H
H H H H

H H H H
H H
H

Alkanes (A homologuous Alkenes (A homologuous Alkynes (A homologuous

series) series) series)
Saturated hydrocarbons. Unsaturated hydrocarbons. Unsaturated hydrocarbons
Contain only single bonds Contain at least one double Contain at least one triple bond
bond.
CnH2n+2 gases CnH2n CnH2n  2
CH4 methane
CH3CH3 ethane CH2CH2 ethene CHCH ethyne
CH3CH2CH3 propane CH2CHCH3 propene CHCCH3 propyne
CH3CH2CH2CH3 butane CH2CHCH2CH3 1-butene CHCCH2CH3 1-butyne
CH3CHCHCH3 2-butene CH3CCCH3 2-butyne
5 carbons pentane 5 carbons pentene 5 carbons pentyne
6 carbons hexane 6 carbons hexene 6 carbons hexyne
7 carbons heptane liquids 7 carbons heptene 7 carbons heptyne
8 carbons octane 8 carbons octane 8 carbons octyne
22 carbons ‘wax’
solids

Note: Larger molecules are solids at room temperature due to increased strength
of London Type Van der Waals Forces.

Structural formulae and models of some

hydrocarbons

Compiled by St John’s College Science Department, adapted by Beaulieu College Science Department

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 A saturated compound is defined as a compound in which all of the bonds
between carbon atoms are single bonds.

An unsaturated compound is defined as a compound in which there is at least

one double and/or triple bond between carbon atoms.

A homologous series is defined as a series of similar compounds which

have the same functional group and have the same general formula, in which
each member differs from the previous one by a single CH2 unit.

6. IUPAC (International Union of Pure & Applied

Chemistry) Naming of Organic Compounds
Hydrocarbons are compounds that contain only carbon and hydrogen atoms.
Molecules that include branched chains of carbon and hydrogen are still called
hydrocarbons. The following diagram represents the compound called
methylpropane. Naming of these structures follows very simple rules defined by
the IUPAC system.

Organic molecules that have atoms or groups of atoms other than carbon to
hydrogen are said to contain functional groups. Because these different types of
atoms or groups of atoms cause the compound to function differently in chemical
reactions they affect the naming of the compound. For example an –OH group
bonded onto a carbon chain turns a simple hydrocarbon into an alcohol. All the
names of alcohols end in – ol. For example: ethanol, methanol, propanol.

A functional group therefore is defined as an atom or a group of atoms that

form the centre of chemical activity in the molecule

Naming depends on:

a) the chain length (this gives the “parent” name).

b) the name and position of functional groups or carbon side chains.

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Rules:
1) Find the longest chain in the molecule and name the molecule from the
number of carbon atoms, according to:

1 = meth 2 = eth 3 = prop 4 = but

5 = pent 6 = hex 7 = hept 8 = oct

2) Establish if there are single, double or triple bonds and add the suffix -ane,-
ene or –yne respectively.

3) Number the carbons along the longest chain starting from the end closest
to a functional group or carbon side chain. To name the carbon side chain
use the same system in rule 1 but add the ending – yl. To name a
functional group refer to the table below.
1 2 3 4 5 5 4 3 2 1
CH3―CH―CH2― CH2―CH3 NOT CH3―CH―CH2― CH2―CH3
| |
CH3 CH3

2-methyl pentane 4-methyl pentane

4) When there is more than one functional group or carbon side chain of the
same kind, the figures indicating the positions of the groups are separated
by commas reinforced by the use of prefixes ‘di’, ‘tri’ etc., for example,

CH3
|
CH3 ―CH―CH―CH3 CH3―CH2―C―CH3
| | |
CH3 CH3 CH3
is 2,3- dimethylbutane is 2,2-dimethylbutane.

5) Different alkyl groups or functional groups are placed in alphabetical order

in the name for a branched hydrocarbon, for example,

CH3―CH2―CH―CH2―CH―CH3
| |
CH2 CH3
|
CH3 is named 4-ethyl-2-methylhexane.

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 HOMOLOGOUS Functional Prefix- or - Example
SERIES group Suffix to
parent name
Haloalkane C-F Fluro- 2-chloropropane
(Alkyl halides) C – Cl Chloro- CH3CHCH3
C – Br Bromo- |
C–I Iodo- Cl
Alcohol C – OH -ol (This is a 1-propanol
suffix so
remove the CH3CH2CH2
last letter of |
ane, ene or OH
yne)
Aldehyde C -al (This is a propanal
(not examinable) | suffix so
CH3CH2CH
C=O remove the
||
| last letter of
O
H ane, ene or
(Carbonyl at yne) (No need to number
end of chain) carbonyl position.
Why?)
Ketone C -one (This is propanone
(not examinable) | a suffix so CH3CCH3
C=O remove the ||
| last letter of O
C ane, ene or
(Carbonyl in yne) (No need to number
middle of chain) for up to 4 carbons.
Why?)
Carboxylic acid C -oic acid Propanoic acid
| (This is a CH3CH2C-OH
C=O suffix so ||
| remove the O
OH last letter of
(Carbonyl at ane, ene or (No need to number
end of chain yne) carbonyl position.
followed by Why?)
OH)
Ester C -oate (This is methylpropanoate
| a suffix so CH3CH2C-OCH3
C=O remove the ||
| last letter of O
OCH3 ane, ene or
(Carbonyl at yne) (Note: Carbonyl
end of chain must be in parent
followed by O name even if it is
and a second shorter)
carbon chain)

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7. Isomers
An Isomer is a compound having the same molecular formula but different
structural formulae.

There are 3 types of structural isomerism :

a. Functional (group) isomerism

These molecules have the same molecular formula but different functional groups.

Eg. C2H4O2 can represent both ethanoic acid (CH3COOH) and methyl
methanoate (HCOOCH3)

b. Chain isomerism
These molecules have the same molecular formula but their chain lengths differ.

Eg. C4H10 can represent both butane (CH3CH2CH2CH3) and methyl

propane CH3CH(CH3)CH3)

c. Position isomerism
These molecules have the same molecular formula but the position of the
functional group on the main chain is different.

Eg. C3H7Br can represent both 1-bromopropane or 2-bromopropane

Exercise 2

Identify the functional groups and draw the displayed structural formulae in each
case.

i) CH2=CHCH(OH)CH3 ii) HCOOH iii) CH3COOC2H5

Compiled by St John’s College Science Department, adapted by Beaulieu College Science Department

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Exercise 3
Name the following:

a) H H H
| | |
H―C―C―C―H
| | |
H H H

b) CH3―CH2―CH―CH3
|
CH2
|
CH3

c) H H H H H H
| | | | | |
HCCCCCCH
| | | | | |
H H CH3 H H H

d) CH3  CH  CH2  CH2  CH2  CH2

 
CH3 CH3

e) CH3

CH3  CH2  C  CH2  CH  CH2  CH3
 
CH3 CH2  CH2CH3

f) 1. H H
H  
C=CCCH These are positional isomers
H   
H H H

2. CH3CH = CH  CH3

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g) CH3
 Note: The chain must be numbered from the
CH3  CH = CH  C  CH3 end nearest the double bond.

CH3

h) CH3  CH = CH  CH = CH2

i) CH3CH(OH)CH2CH2CH2CH2(OH)

j) 1. CH  C  CH2  CH3

2. CH3C  C  CH3

O
k) CH3CH2CH2C
OH

l) O
CH3CH2  C
OCH2CH3

m) CH3CH2CCH

Exercise 4
Write structural formula for:

a) 2,4-hexdiene

b) 2-methylheptane

c) 2,3-dimethylbut-2-ene

d) The three chain isomers of C5H12

e) 2-Bromo-5-methylhexane

(Why would 5-bromo-2-methylhexane be incorrect for this structure)

NOTE: Side chains are called alkyl substituents. A substituent is an atom or group
of atoms bonded to a carbon chain. This can be an inorganic atom (e.g. halogen)
or an alkyl group that is shorter than the main chainp.

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8. Reactions of Alkanes
Alkanes are fairly unreactive because of the lack of polarity in the bonds and due
to the strength of the bonds. They do, however, burn readily and undergo
substitution with free radicals.

Many organic compounds are flammable. Suggest a suitable method of heating

organic liquids:

_________________________________________________________________

_________________________________________________________________

a. Combustion Reactions
Fossil fuels like octane (petrol) react and transfer chemical potential energy into
heat energy (exothermic). The following equations show the complete combustion
of an alkane with excess oxygen.

CH3CH2CH3 + 5O2  3CO2 + 4H2O H < O

C8H18 + 12 ½ O2  8CO2 + 9H2O H < O

Candle wax, petrol, town gas are all examples of alkanes which burn according to
the oxidation reaction above.

b. Substitution Reactions
Substitution reactions are reactions when one atom or molecular fragment is
replaced in a molecule by another. In alkanes, due to the lack of polarity and due
to the strength of the bonds, the attacking species is a free radical. These
reactions are slow reactions and take place in the presence of light which forms
the free radicals. You must be able to distinguish between halogenation and
hydrolysis as specific types of substitution

Examples of halogenation: alkanes to haloalkanes

CH3CH3 + Cl2  CH3CH2Cl + HCl

CH4 + Br2  CH3Br + HBr
CH4 + 4Cl2  CCl4 + 4HCl
C5H12 + Br2  C5H11Br + HBr

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These reactions takes place in the presence of UV light or heat.

Examples of hydrolysis: haloalkanes to alcohols

CH3Cℓ + NaOH(aq)  CH3OH + NaCℓ

(see reactions of haloalkanes)

These reactions take place in the presence of heat under reflux in a dilute alkali
solution

c. Elimination Reactions
An elimination reaction is one where atoms or molecular fragments are removed
from adjacent carbon atoms on a molecule leaving a double bond with nothing
else having been added.

One commercially important elimination reaction is known as cracking.

In this reaction large hydrocarbon molecules are broken into smaller and
more useful molecules. These reactions producing at least one alkene.

There are two types of cracking that can take place:

 Thermal cracking takes place under high pressures and high

temperatures without a catalyst.

 Catalytic cracking takes place under lower temperatures and

pressures but a catalyst is needed.

e.g. C12H26  C8H16 + C4H8 + H2

CH3CH3  CH2CH2 + H2

Exercise 5
a) Write a balanced combustion reaction equation for pentane.

b) Bromine reacts with propane in the presence of light.

i) Why is the propane relatively unreactive?

ii) How is the bromine radical formed?

iii) Write a complete balanced equation for the reaction where two bromine
atoms substitute onto the propane.

c) Write an equation for the elimination reaction of propane.

Compiled by St John’s College Science Department, adapted by Beaulieu College Science Department

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9. Reactions of Haloalkanes
a. Substitution Reactions
Haloalkanes are fairly reactive because of the polarity in the C-X bond.
Substitution reactions are reactions when one atom or molecular fragment is
replaced in a molecule by another. In haloalkanes substitution ractions are faster
than substitution reactions in alkanes due to the added polarity of the C-X bond.

The attacking species can be either the lone pair on H2O or OH and attacks a
positive side of a polar bond. In both cases the effect is to substitute the halogen
with OH-.

Examples of haloalkane substitution in aqueous medium:

CH3Br + OH-  CH3OH + Br-

CH3I + NaOH  CH3OH + NaI

CH3Cl + NaOH  CH3OH + NaCl (Slow due to C-Cl bond strength)

CH3Br + H2O  CH3OH + HBr

The effects of the solvent

Consider the following diagrams showing the dissolution of the hydroxide ion in
water and in ethanol. The intermolecular bonding in both cases involves ion-
dipole type van der Waals bonding.

Hydroxide ion

In an aqueous
solvent (small H2O molecules), the OH- molecules can approach the C-X bond
and substitute.

In an alcohol solvent (larger ethanol molecules) OH- cannot get close enough to
the C-X bond so elimination occurs.

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b. Elimination Reactions
Elimination reactions dominate between a haloalkane and hydroxide when the
solvent is changed from water to ethanol.

+ OH–(ethanol) + H2O + X

Where X = F, Cl, Br or I

Exercise 6
Consider the reaction of 2-chloro-2-methylbutane reacting with sodium hydroxide.

a) State the conditions that are required to produce an alkene.

b) Draw the displayed structural formula of the organic product formed when
elimination takes place.

c) Name the type of reaction that takes place when the OH- is hydrated.

d) Write down a balanced reaction equation for the substitution process. Use
condensed structural formulae.

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10. Reactions of Alkenes

Alkenes are fairly reactive even though the bond is not polar. The “second bond”
in the double bond is relatively weak and rich in electrons and allows reactions
where attacking species have an ability to accept a lone pair (H +, or H in polar
bond like HCl).

a. Combustion Reactions
Like other hydrocarbons alkenes burn in oxygen forming carbon dioxide and
water. They are not often used as fuels due to their suitability as starting reactants
for many organic reactions. The alkenes have a greater tendency to undergo
incomplete combustion when compared with alkanes due to the double bond.
Incomplete combustion involves the production of carbon monoxide and carbon
rather than carbon dioxide and water.

The following equation represents the complete combustion of pentane.

C5H12 + 8O2  5CO2 + 6H2O

b. Addition Reactions
An addition reaction is a reaction where a double bond opens and new molecular
fragments are added to the molecule at both ends of the double bond without
anything being removed.

Examples of specific types of addition reactions follow:

CH2 = CH2 + HCℓ  CH3-CH2Cℓ (known as hydrohalogenation)

CH2 = CH2 + H-OH  CH3-CH2OH (known as hydration)

CH2 = CH2 + Br2  CH2Br –CH2Br (known as halogenation)

CH2 = CH2 + H2  CH3-CH3 (known as hydrogenation)

These reactions occur easily and in the case of the bromine the reaction causes a
colour change (from brown to colourless). This reaction is used as a test for the
presence of alkenes. Often the rate of halogenation of cyclohexane is compared
with cyclohexene. Which would be slow and why?

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Application of reaction

Cooking oil, normally sunflower oil, contains long carbon chains with many double
bonds. These molecules are known as poly-unsaturated compounds. The double
bond does not allow rotation around the bond and these molecules are rigid.
Rigid long chained molecules do not tangle together and therefore move over
each other easily accounting for the oil like viscosity. Viscosity can be defined as
the fluids resistance to flow. On hydrogenation a percentage of the double bonds
become single bonds and the molecule becomes less rigid as rotation can take
place around the single bond. Hydrogenated oils become thicker due to
increased tangling and are known as margarines.

Exercise 7

Consider the reaction of HBr with propene.

a) Discuss the type of bond within HBr and identify the polarity of this
molecule.

b) What part of propene makes it reactive towards the HBr?

c) Write a balanced chemical equation for this reaction.

d) What possible product would form if water was used as a solvent?

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11. Reactions of Alcohols
When considering the polarity of the bonds in alcohols the possibility of reactivity
is evident.

 2–
O

+R H +

 The lone pair on the O atom can attack atoms than can accept a lone pair (e.g.
H+ or the positive side of a polar bond as with carboxylic acids C=O)
 Halide can attack Alkyl (R)
 Polarity of O-H results in intermolecular hydrogen bonds.

a. Combustion
Like other hydrocarbons alcohols burn in oxygen forming carbon dioxide and
water. They are often blended with octane and can be manufactured through
fermentation of plant sugars like sucrose, extracted from sugar cane. The
following reaction represents the complete combustion of ethanol.

CH3CH2OH + 3O2  2CO2 + 3H2O

b. Elimination Reactions
The elimination of water from an alcohol is known as a dehydration reaction and
requires a acid catalyst. The reaction equation follows:

CH3CH2OH  CH2= CH2 + H2O

Exercise 8:

a) The dehydration reaction of 2-butanol (butan-2-ol) using hot pumice and

aluminium oxide produces two possible structural isomers.

b) Draw displayed formulae of the two possible isomers and name each.

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12. Esterification
c. H2SO4 catalyst
Carboxylic acid + alcohol ester + water
Heat

H H H H H + H20
O      O
CH3C HO  C C  C  C  C  H CH3C H H H H H
OH      OC C C CCH
H H H H H H H H H H

ethanoic acid pentanol  pentyl ethanoate + H2O

(Banana smell)

From acid

O
CH3  C
OR From alcohol

R  parent name  oate

Exercise 9

a) Write a balanced chemical equation for the reaction of ethan-1-ol with

propanoic acid.

b) Consider the following ester, Pentyl propanoate.

i) Name of the alcohol reacted to produce this ester.

ii) Name the carboylic acid reacted to produce this ester.

iii) What is the function of the sulphuric acid?

iv) Name the molecule that is condensed out of this reaction.

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13. End of Chapter Examples
1. Aspirin is used as a pain-killer and is found in the bark of the Willow tree.
The structure of aspirin is shown. OH

C
O

O C CH3

What functional groups are present in aspirin.

i Alcohol

ii Carboxylic acid

iii Ester

A) i only

B) i and ii only

C) ii only

D) ii and iii only

2. The correct IUPAC name for the organic molecule with the following
structural formula is:

OH

CH3  C  CH2  CH2  CH  CH2  CH3
 
H CH2  CH2 CH3

A) 3-propyl heptan-6-ol

B) 5-propyl heptan-2-ol

C) 4-ethyl octan-7-ol

D) 5-ethyl octan-2-ol

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3. (IEB Paper II 1999)
The boiling point of decane (C10H22) is 174°C. At the same atmospheric
pressure the boiling point of butane is -0,5 °C. The reason that decane has
a higher boiling point than butane is because decane …
A has more hydrogen atoms
B has stronger hydrogen bonds between molecules
C is a branched hydrocarbon
D has stronger London type van der Waals forces between the
molecules

4. Consider the fermentation reaction:

zymase
C6H12O6  Product 1 + Product 2

The enzyme zymase breaks the sugar, glucose, into two products. The
two products formed are:

A CO and CH3OH
B CO2 and CH3CH2OH
C C and H2O
D CO2 and CH3OH

5. Compound A can be oxidised by acidified potassium dichromate to

form a carboxylic acid. The functional group of compound A is:

A - OH B - COOH

C -CH2CH2- D - COO-

6. A number of organic compounds are listed below in the form of their

molecular or condensed structural formulae.

A CH3CH2CH2CH3

B CH3CH2CH2Cl

C C2H6

D CH3COOH

E C2H4

F CH3OH

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Select from the list:

a) An acidic substance.

b) An unsaturated hydrocarbon.

c) Two compounds that can react together to form an ester.

Now, using the list, answer the following questions:

d) Write down the structural formula of an isomer of compound A

e) Write the molecular formula of the two compound(s) that would form if
compound C reacted with Cl2 gas under the action of sunlight.

f) Write down the structural formula of the compound formed when E reacts
with water under suitable conditions in an addition reaction.

7. Consider the following table of boiling points for alkanes and alcohols.

a) Explain the general increase in boiling point moving down from methane to
hexane and from methanol to 1-hexanol.

b) Draw the functional group of the alcohols.

c) Define functional group.

d) Explain why the alcohol, with the same number of carbon atoms, has a
larger boiling point compared to the alkane.

Alcohols can be made by the fermentation of sugar from plants. These sugars are
produced during photosynthesis. The photosynthesis reaction can be
summarised by the following chemical equation:

6CO2 + 6H2O → C6H12O6 + 6O2

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Alcohols can be used as fuels as their combustion reactions are exothermic.

e) Write the balanced chemical equation for the combustion of 1-propanol.

f) When alcohol is produced from plant sugars it is considered to be

renewable. When burnt as a fuel it is considered to be carbon neutral.
What is meant by the term carbon neutral?

g) When 1-propanol is passed over heated aluminium oxide granules, as

represented in the diagram below, a reaction takes place. (Aluminium
oxide does not take part in the reaction).

i) Write an equation for the reaction that takes place.

ii) Name the type of organic reaction taking place.

iii) Suggest why the liquid propan-1-ol needs to be soaked into ceramic
fibre or glass wool?

iv) Draw the structural formula of the organic product of this reaction.

v) Consider the table of boiling points above. Estimate a boiling point

of the organic product of this reaction.

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 vi) The organic product of this reaction can undergo a number of
reactions. Describe two reactions that this organic product will
undergo.

8. Taken from DBE.

Organic chemistry is the study of carbon and the chemistry of its compounds.
One of the simplest ways of representing this chemistry is to draw reaction
pathways as below.

Consider the following sequence of organic reactions and then answer the
questions that follow. Reactions are labelled from A to F while molecules are
labelled from I to V

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8.1. What is meant by the term ‘homolegous series’?
8.2. Identify the homolegous serues to which the following molecules belong:
a) II
b) III
c) IV
8.3. Name the general and specific types of reactions labelled A, C, D and E in
the rection sequence provided.

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8.4. Consider reaction B. To form this molecule labelled IV, a reaction takes
place between molecule III and another molecule from a different
homolegous series

a) Name the homolegous series to which the other molecule belongs.

To prepare molecule IV in the laboratory, the two reactants are mixed

together in a test tube. A few drops of concentrated sulphuric acid are added
and the test tube is placed in a hot water bath and then heated as shown
below.

b) Why do you think the test tube must be heated in a hot water bath?
c) Sulphuric acid is often used as a catalyst in this reaction. Explain what
is meant by the term catalyst.
d) Name another function of the suphuric acid in this reaction.
e) Where in everyday life, would molecules of this newly formed substance
most likely be found?

9. There are two possible types of isomers of organic molecules that have the
molecular formula C4H8O2.

a) Explain what is meant by the term ‘isomer’.

b) Name the homolegous series to which each of these isomers belongs
c) Which of these isomers will have the highest boiling point?
d) Explain your answer in (c) fully.

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14. Some suggested investigations
Name: ___________________________

Some of this practical has been adapted from the University of Cambridge
International Examinations 2006 ©
Safety
 You must wear eye protection throughout these experiments.
 Alcohols are highly flammable.
 Methanol is highly flammable and Toxic.
 Sodium dichromate(VI) is highly toxic and irritant.
 Dilute sulphuric acid (1 mol dm1 ) is irritant.
 Concentrated sulphuric acid and glacial ethanoic acid are corrosive.

Instruction for Students:

Each group should fill the small 100 cm 3 beaker with water to clean the teat
pipettes. Dry them with garage roll. You must not contaminate the bench
chemicals with dirty equipment. Don’t take too much chemical. Discard excess
chemical in the waste deposit bottles and not back into the bench chemicals.

Experiment 1: Addition VS Substitution

Aim: To compare the reactions of cyclohexane and cyclohexene with bromine.
 Add a few drops of approximately 2% solution of bromine in an inert solvent
to approximately 2 cm3 of liquid cyclohexane and liquid cyclohexene, in
separate test-tubes.
 Compare colours of the solutions.
 Place the test-tube containing the alkane and bromine in inert solvent in the
sunlight and leave for a while.
 Observe the appearance of the solution.
H H H H
H H H
H
H
H
H H
+ Br2 H Br

H
+ HBr
H
H H H H
H H H H

H H H H
H
H H H
Br
H
+ Br2 H
H
H H
Br
H H
H
H H H H

a) Which reaction takes place at the greatest rate?

b) Suggest why the one reactant is more reactive than the other with bromine.

c) Why is the alkane placed in the sunlight?

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Experiment 2: (Substitution of haloalkanes)

To compare the rates of reaction of chloro, bromo, and iodobutane with water.

 Mark 3 test-tubes from the rack of 6 as chloro, bromo and iodo.

 Add three drops of 1-chlorobutane to the first test-tube, three drops of 1-
bromobutane to the second test-tube and three drops of 1-iodobutane to the
third test-tube.
 Add 2 cm3 of ethanol to each of the labeled test-tubes to act as a solvent.
 Add 2 cm3 amounts of 0,02 mol/dm-3 silver nitrate solution in three separate
unlabeled test tubes that remain in the rack of 6.
 Prepare the 100cm3 beaker as a water bath by heating 50 cm3 of water on the
spirit burner stand.
 Add the 2 cm3 portions of silver nitrate solution, simultaneously and as quickly
as possible, to each of the solutions in the three labeled test-tubes
 Place the labeled test-tubes into the beaker which acts as a heating bath.
 Record the relative times when the various precipitates appear

Compound Relative time for precipitate to appear/s

1-chlorobutane
1-bromobutane
1-iodobutane

a) Write down a chemical reaction to illustrate the reaction between a

haloalkane and water.

Consider the following data:

Bond Bond polarity (difference in Bond energy (kJ/mol-1)

electronegativity)
C―Cl 0,5 346
C―Br 0,3 290
C―I 0,0 228

b) Which factor (bond polarity or bond energy) appears to be more important

when considering the relative rates of reaction of the three haloalkanes?
Explain.

Experiment 3 (Elimination of a haloalkane)

Place approx. 2 cm3 of 20% KOH in ethanol in a boiling-tube and add 0,5 cm3 of
2-chloro-2- methylpropane. Push a
plug of ceramic/glass fibres into
the mixture and arrange the test-tube for
the collection of a gas. Heat gently and

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collect two or three test-tubes of gas. Test the gas for flammability and also test
with bromine water.

a) Write down your observations for this experiment:

b) Name the type of reaction taking place between the bromine and the
gaseous product formed.

c) Write a combustion reaction for the product formed.

Experiment 4 Elimination Reaction of an Alcohol

NB: Wear safety glasses.

 Place the spirit burner in the hole in the front left of the board and not under
the stand. Fill it but do not light it at this point.
 Erect the retort stand next to the spirit burner.
 Clamp the medium sized test-tube so that it lies almost horizontally and
with the middle of the test-tube above the spirit burner, as shown in the
diagram.

Ethanol
soaked Aluminium
glass wool oxide

Water

 Soak some glass wool with ethanol and push it down to the bottom of the
test-tube.
 Carefully place two spatula quantities of aluminium oxide powder in the
middle of the test-tube, directly above the heating area.
 Stopper the test-tube with the single-holed stopper and delivery tube.
 Fill, within 1cm from the top, the largest test tube with water and insert the
stopper with two holes.
 Insert the end of the delivery tube into the smallest of the stopper's holes.
Place this large test-tube upright into a hole in the board.
 Light the spirit burner and make sure that constant heating is maintained
until the gas has been collected. This will prevent “suck back”.

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  When the aluminium oxide is hot, invert the large test-tube containing water
into a beaker to collect the gas. If no gas is produced it may be necessary
to slide the medium test-tube forwards, so that the alcohol in the glass wool
is also heated periodically. If this is done move the test-tube back to the
position where the aluminium oxide gets direct heat.
 When sufficient gas has been collected remove the large test-tube from the
beaker and remove the stopper. Replace the two holed stopper with a
solid stopper. Do not allow the end of the delivery to drop into the beaker
of water as water can be sucked back into the test-tube containing zinc.

a) Write a balanced chemical equation for the elimination reaction

 Test the gas which is collected by adding a small amount of bromine water.
Immediately, after this follow by inserting a lighted splint.

b) Write an equation for the reaction where bromine acts as a test for the

alkene produced.

c) What type of reaction is this?

d) Write an equation for the combustion reaction of the alkene.

Experiment 5. Combustion
Place about 1 cm3 of ethanol in a small crucible and ignite using a burning splint.
Place a test-tube half-full of cold water directly above the flame for a small fraction
of a second. Record your observations.

a) What test could be done to confirm the identity of the product produced on
the boiling tube.
b) Write an equation for this combustion reaction.

Experiment 6. Formation of an Ester

Caution: Collect the concentrated sulphuric acid from your teacher. Do not use
the diluted H2SO4 which is available on the bench.

In a medium test-tube from the rack of 6, make a mixture of 10 drops of ethanol

(or isobutyl),
5 drops of methanoic acid or propanoic acid and 3 drops of concentrated
sulphuric acid. The concentrated sulphuric acid must be collected from your
teacher. Half fill a 100 cm3 beaker with hot water and keep the mixture warm for
5 minutes. Start experiment 9 during this period. Add about a spatula quantity of

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solid sodium carbonate followed by approximately 20cm 3 of water. This will
neutralise any remaining acid and allow you to smell the sweet aroma.

a) What smell is produced?

b) What is the function of the sulphuric acid?

c) What type of reaction occurs between the alcohol and a carboxylic acid? ---
d) Write a balanced equation for this reaction.

The flow charts on the next pages can be used to practice the different

types of reactions (Thanks to K Mc Neil)

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Your own notes:

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