BASIC CONCEPTS OF
ORGANIC CHEMISTRY
Prepared by Dr. Zahoor Islam
Pharm.D, RPh, MPhil, Ph.D. Scholar
Youtube: Zahoorislamofficial
Email:
[email protected] OBJECTIVES
Recognize the importance of organic compounds.
Compare properties of organic and inorganic
compounds
Describe classification of organic compounds.
Differentiate the types of Hydrocarbons (Saturated
and unsaturated Hydrocarbons).
Describe the molecular composition of carbohydrates,
proteins, fats, Nucleic acid.
List the functional groups that is alcohol, ethers
aldehydes, ketones, acids, esters, amines, amino
acids, and amides.
Write equations for the formations of alkene, alkanes,
aldehydes, ketones, acids, esters, amines and amides.
Discuss the biologic importance of various aldehydes,
ketones, acids, esters, amines, amides.
Distinguish between primary, secondary and
tertiary amines.
Explain the structure of amino acid (amino acid ).
Discuss isomerism with at least two examples.
Organic Chemistry- The study
of carbon & carbon compounds
Organic compounds are the
primary constituents of all
living organisms.
Draw an electron dot diagram of carbon.
Χ●
●
Χ
C
Χ●
●
Χ
Carbon is able to form 4 covalent
bonds (4 valence electrons) with
other carbon or other elements.
II. CHARACTERISTICS OF
ORGANIC COMPOUNDS
Theyare nonpolar compounds – they
do not dissolve in polar solvents like.
Water
O-
H
H+
+
*remember the rule –
“likes dissolve likes”
4) They have low melting points –
due to weak intermolecular forces.
C-C ● ● ● C-C
STRONG STRONG
weak
5) They react slower than ionic
compounds – due to strong
covalent bonds between atoms.
Structural Formulas –
A 2D model shows bonding patterns and
shapes of molecules
Carbon is found in the center H
H C H
The short line – represents a
H
pair of electrons.
EACH
ORGANIC
H
1. Methane: CH4
H C H
H H
2. Chloroform: CHCl3
Cl C Cl
Cl H H
3. Ethane: C2 H6
Remember : Carbon H C C H
has 4 bonding sites. H H
Types Of Bonds
Single Bond – single covalent bond in
which they share 1 pair of electrons. (2 e-)
● ●
C C ● C ● ● C ●
● ●
Double Bond – carbon atoms may
share 2 pairs of electrons to form a
double bond.
● ●
●●
C C ●
C ●● C●
Triple Bond – carbon atoms may share
3 pairs of electrons to form a triple bond.
C C ●●
●C ●● C●
●●
Types Of Compounds
Saturated Compound – organic
compounds in which carbon atoms
are bonded by SINGLE bonds.
ex. Methane: CH4
H
H C H
H
Types Of Compounds
Unsaturated Compound – compounds
where carbon atoms have double or
triple bonds.
ex. ethene: C2H4
H H
H C C H
HOMOLOGOUS SERIES OF
HYDROCARBONS
Organic compounds can be
classified into groups with related
structures and properties.
***As size of molecule increases the
boiling and freezing points increase.
HYDROCARBONS ARE ORGANIC
COMPOUNDS THAT CONSIST OF ONLY
CARBON AND HYDROGEN ATOMS.
H H H
H C H H C C H
H H H
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single
● Saturated hydrocarbons
ALKANES = CNNH2N+2
2N+2
• A saturated hydrocarbon contains 5
carbons. What is the formula?
C5H2(5)+2 =C5H12
A saturated hydrocarbon contains
20 carbons. What is the formula?
C20H2(20)+2 = C20H42
Saturated = Single
ALKANES
CH4 = methane
C2H6 = ethane
C3H8 = propane
C4H10 = butane
C5H12 = pentane
The smaller the compound the Lower Boiling
point and Melting point is (less bonds to break)
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NAMING ORGANIC COMPOUNDS
Organic compounds are named according to the
IUPAC (international union of pure & applied
chemistry) system of nomenclature.
Alkanes – end in ane
Alkenes – end in ene
Alkynes – end in yne
ALKENES – CNH2N
SERIES OF UNSATURATED
HYDROCARBONS HAVING ONE
DOUBLE BOND (C=C)
Also called ethylene
series (IUPAC name
is ethene)
General formula
CnH2n
ALKENES
C H4 = Ethene
2
C H6 = Propene
3
C H8 = Butene
4
C H10 = Pentene
5
Tofind the number of
hydrogens, double the
number of carbons.
1-BUTENE
This is 1-butene, because the double
bond is between the 1st and 2nd carbon
from the end.
PENTENE
This is 1-pentene. The double bond is
on the first carbon from the end.
This is not another isomer of pentene.
This is also 2-pentene, just that the
double bond is closer to the right end.
ISOMERISM
Isomerism is the phenomenon in which more
than one compounds have the same
chemical formula but different chemical
structures.
Chemical compounds that have identical
chemical formulae but differ in properties
and the arrangement of atoms in the
molecule are called isomers.
For example: Ethyl alcohol and dimethyl
ether are isomers of each other as both the
compounds have the same molecular
formula – C2H6O or C2H5OH while different
structural formulae.
ETHYL ALCOHOL VERSES DIMETHYL
ETHER
ALKYNES –
A SERIES OF UNSATURATED
HYDROCARBONS THAT CONTAIN 1
TRIPLE BOND.
Also called the acetylene series
General formula CnH2n-2
C C
ALKYNES
• C2H2 = Ethyne
• C3H4 = Propyne
• C4H6 = Butyne
• C5H8 = Pentyne
ALKYL GROUPS – HAVE ONE LESS
HYDROGEN THAN THE CORRESPONDING
ALKANE.
CH is methyl – one less H
3
than methane, CH4
H
H C H
H
Draw methyl
C2H5 is ethyl – one less H than ethane C2H6
Condensed
Formula:
CH22CH33
Ethane
C3H7 is propyl – one less H than propane C3H8
propane
BENZENE – A SERIES OF
CYCLIC UNSATURATED
HYDROCARBONS.
General formula CnH2n-6
Benzene – C6H6 the simplest in the family
H
C
H
H
C C
H C C H
C
H
IUPAC NAMING
BRANCHED
HYDROCARBON
CHAINS
SOMETIMES THE HYDROCARBON CHAINS ARE NOT
STRAIGHT AND SOMETIMES THEY HAVE OTHER
ELEMENTS ATTACHED TO THEM. HERE IS HOW
THEY ARE NAMED:
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
Step 1: Find the longest continuous chain
of carbons.
All bonds in the chain of carbons
are single bonds so ending is…ane.
There are 7 continuous carbons, so the
parent chain is heptane.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
4 5 6 7
1 2 3
CH2 CH3 CH3
CH3
Step 2:
Number the carbons in the main
sequence starting with the end that will give
the attached groups the smallest #.
This chain is numbered from right to left because
there is a substituent closest to the right.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
Step 3 : Add numbers to the names of the groups to
identify their positions on the chain.
- these numbers become prefixes to the parent
chain. yl
ethane
In this ex. the positions are:
C2H6
5
2 - methyl, 3 - methyl, 4- ethyl
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
Step 4: Use prefixes to indicate the appearance of a
group more than once in the structure.
Di = twice
Tri = three times
Tetra = four times
Penta = five times
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
This chain has 2 methyl groups so
dimethyl is used.
Step 5: List the alkyl groups in alphabetical
order.
In this ex. dimethyl is listed before the
ethyl.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
Step 6: Use punctuation
- use commas to separate numbers
-hyphens to separate numbers with
words.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
The name of this compound is:
2,3-dimethyl – 4-ethyl heptane
CH3 CH3
CH3 - CH2 – CH – CH2 – CH - CH3
6 5 4 3 2 1
Step 1: 6 carbons hex =
All single bonds = ends in ane
So parent chain is hexane
Step 2: start numbering from right to left
Step 3: 2 -methyl and 4 -methyl
CH3 CH3
CH3 - CH2 – CH – CH2 – CH - CH3
6 5 4 3 2 1
2,4 dimethyl hexane
When naming with a double/triple bond-
start # carbons closest to the bond.
CH3 CH3
C 1 C2 C3 C4 C5
3,4 dimethyl, 2-pentene
NOW START WITH NAME AND DRAW THE
STRUCTURE.
3-ethylhexane
C C C C C C
CH2
CH3
You can place H’s all around or just leave as is.
H C H
yl
H C H ethane
C2H6
H 5
2,2,4-trimethylpentane
CH3
C C C C C
CH3 CH3
OTHER ORGANIC COMPOUNDS
Functional Groups – specific groupings of atoms that give
characteristic properties to organic compounds.
halides F (fluoro-)
Cl (chloro-)
Br (bromo-)
I (iodo-)
What group do these belong to?
Halogens
Alcohols -OH hydroxyl
Organic acids -COOH carboxyl
Aldehydes O -CHO carbonyl
Ketones
-C-
Ethers -O- O
Esters -C-O
Amines -N- O
Amides -C-NH
HALIDES
Cmpds that are formed
when any halogen
(F,Cl,Br,I) replaces an
H atom in an alkane.
The functional
group is the halide
(F,Cl,Br,I)
HALIDES
They are named by citing the location of the halogen
attached to the chain
Halides are binary compounds made up of any other
element and a halogen.
Drop the “ine” and add “o”
F
2- fluoropropane
ALCOHOLS
Are organic compounds in which one or more of
the hydrogens is replaced with an – OH group.
- OH group is called the hydroxyl group
MONOHYDROXYL ALCOHOLS
-HAVE ONE –OH GROUP
H
R C OH
H
Shortcut way to represent a primary alcohol
R-OH
R stands for REST of the molecule
IUPAC NAMING OF ALCOHOLS
Replace the final “e” with “-ol”
● methane methanol CH3OH
● ethane ethanol C2H5OH
● propane propanol C3H7OH
● butane butanol C4H9OH
● pentane pentanol C5H11OH
EX. 2-PROPANOL
H OH H
H C C C H
H H H
1 2 3
ORGANIC ACIDS – HAVE THE FUNCTIONAL
GROUP -COOH
R-COOH
O
Carboxyl
R C
group OH
IUPAC NAMING OF ORGANIC ACIDS
Replace the final “e” with “-oic ”acid
H
Methanoic acid - HCOOH O H C H
R C H
OH
ALDEHYDES- CONTAIN THE
FUNCTIONAL GROUP -CHO
R-CHO O
R C
H
IUPAC NAMING OF ALDEHYDES-
Replace the final “e” the ending “al”
First member of the aldehyde family is methanal
-its common name is formaldehyde
Used to
2 O preserve
H C 3 biological
1 samples
4 H
Try this one:
Ex.) C2H4 + Br2 C2H4 Br2
This is a addition Reaction
What process makes…
saponification
combustion
fermentation
addition
polymerization
Condensation
polymerization
AMINES CLASSIFICATION
Amines are classified as primary, secondary, or tertiary
by the number of carbons bonded to the nitrogen atom.
Primary amine has one carbon bonded to the nitrogen.
Secondary amine has two carbons bonded to the
nitrogen
Tertiary amine has three carbons bonded to the nitrogen
THANK YOU FOR YOUR
TIME
