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Chapter 4 Introduction of Organic
Chapter 4 Introduction of Organic
Chapter 4 Introduction of Organic
INTRODUCTION
TO
ORGANIC CHEMISTRY
CHAPTER 11 :
INTRODUCTION TO
ORGANIC CHEMISTRY
11.1 Introduction
11.2 Empirical molecular and structural formulas
11.3 Functional groups and homologous series
11.4 Classification of carbon atoms in organic molecules
11.5 Isomerism
11.6 Reactions in organic compound
11.1 INTRODUCTION
CH3 CHCOOH
CH4
NH2
methane alanine
(a component of natural gas) (amino acid-a protein component)
OCOCH3 CH3
N
CO2CH3
COOH
OCO
dichlorodiphenyltrichloroetane
(DDT- a pesticide component)
CH2 NH S
C
N
O
COOH
4-hydroxyphenylazobenzene
(a kind of dye)
CH3
O
H3C N
N
N
O N
CH3
H 2N C NH 2
Urea
(a component in urine,
also used as fertilizer)
therefore,
Solution :-
relative molecular mass
n= empirical formula mass
60.0
= =2
12.0 2.0 16.0
= (CH2O)2
= C2H4O2
Example 2 :
Element C H
Mass (g) 85.7 14.3
Moles (n) 85.7 14.3
= 7.142 = 14.3
12.0 1.0
Smallest ratio 7.142 14.43
7.142 7.142
=1 =2
a) Condensed Structure
b) Expanded Structure
c) Skeletal Structure
d) 3-Dimensional formula
e) Ficher Projection
The structural theory of organic chemistry
C O H Cl
Carbon-carbon bonds
C C C C C C
CH3CHCH2CH3 or CH3CH(Cl)CH2CH3
C4H9Cl
Cl
Condensed structure
b) Expanded Structure
Example :
H H H H
C4H9Cl
H C C C C H
H Cl H H
Expanded structure
c) Skeletal Structure
Example :
1. CH3CH(Cl)CH2CH3 =
Cl
2. H2C CH2
=
H2C CH2
3. CH2=CHCH2OH =
OH
Practice Exercise :
2. (CH3)2CHCH2CH2CH(CH3)CH2CH3
Example : Br Indication :-
bonds that lie in the
(Bromoethane) H plane of the page
C H
bonds that lie behind
the plane
H
bonds that project out
of the plane of the
paper
Br H H
OR OR
C C C
H H H Br H H
H H Br
e) Fischer Projection
2 – butanol , CH3CH(OH)CH2CH3
CH3 CH3
HO H OR
H OH
CH2CH3 CH2CH3
11.3 FUNCTIONAL GROUPS AND
HOMOLOGOUS SERIES
CH3OH (methanol)
} The different by –CH
2
CH CH OH (ethanol)
3 2
CH CH CH OH (propanol)
} The different by –CH 2
3 2 2
4. There is a trend in the physical properties of the
members of any homologous series.
aromatic
ring methylbenzene
depending on the
number of carbon
atoms bonded to it
A primary carbon – directly bonded to one other
carbon atom
(has 1 adjacent carbon atom)
Example :
1oH
H C H
CH3
1o carbon
A secondary carbon – directly bonded to two other
carbon atoms
(has 2 adjacent carbon atoms)
Example :
2o H
H
H C CH3
CH3
2o carbon
A tertiary carbon – directly bonded to three other
carbon atoms
(has 3 adjacent carbon atoms)
Example :
CH3
3o H H C CH3
CH3
3o carbon
A quarternary carbon – directly bonded to four other
carbon atoms
(has 4 adjacent carbon atoms)
Example :
CH3
H3C C CH3
CH3
4o carbon
Similarly, a hydrogen atom is also classified as
primary, secondary or tertiary depending on the
type of carbon to which it is bonded.
H C C Cl
H H 2° C
H H H
1° alkyl chloride
H C C C H
H Cl H
3 C
°
H CH3 H
2° alkyl chloride
H C C C H
H Cl H
3° alkyl chloride
Classification of alcohols
H C C OH
H H
2° C
1° alcohol H H H
H C C C H
H OH H
3° C
H CH3 2° alcohol
H
H C C C H
H OH H
3° alcohol
Classification of amines
H3 C N H CH3
N bonded to
two alkyl group
H
A primary (1°) A secondary (2°)
amine amine
H3 C N CH3
Isomerism
structural isomerism
Two types different order of attachment
of of atoms
isomerism
stereoisomerism
different spatial arrangement of
atoms in molecules
Structural isomers are different compounds with
the same molecular formula but differ in the order
of attachment of atoms
Structural isomerism
Example :
CH3CH2CH2CH2CH3
CH3
C5H12 :
CH3CHCH2CH3 CH3-C-CH3
CH3 CH3
b) Positional isomerism
These isomers have a substituent group in
different positions in the same carbon skeleton
Example :
1-chloropropane Cl
2-chloropropane
1,2-dimethylbenzene
CH3
CH3
1,4-dimethylbenzene
CH3
1,3-dimethylbenzene
c) Functional group isomerism
O O
propanal propanone
a) Geometric isomerism
cis-2-butene trans-2-butene
cis-1,2-dimethylcyclohexane trans-1,2-dimethylcyclohexane
Cl Cl
iv) Cl H
H H
H Cl
cis-1,3-dichlorocyclopentane trans-1,3-dichlorocyclopentane
If one of the doubly bonded carbons has 2 identical
groups, geometric isomerism is not possible.
Examples :
2-methyl-2-butene 1-chloro-2-methylpropene
cis-trans isomers have similar chemical properties
but different physical properties
P
PQRS
C*
Q S *designates chiral centre
R
Enantiomers are a pair of mirror-image molecules
that are not superimposable (must have one or more
chiral carbons)
Examples :
i) 2-butanol, CH3CHCH2CH3 :-
OH
CH2CH3 CH2CH3
C* C
H3C H CH3
H
OH OH
enantiomers
ii) 2-hydroxypropanoic acid, CH3CHCOOH :-
OH
COOH COOH
H OH HO H
CH3 CH3
enantiomers
A racemic mixture or racemate is an equimolar
mixture of enantiomers which is optically inactive
because the two components rotate plane-polarized
light equally (same degree of rotation but in opposite
direction– so they can cancel each other’s rotation)
COOH COOH
H NH2 H2N H Four pairs of
A B diastereomers
H OH HO H
are identified :
CH3 CH3
enantiomers A and C ;
A and D ;
COOH COOH B and C ;
H NH2 H2N B and D
H
C HO H H OH
D
CH3 CH3
enantiomers
Meso compound is a stereoisomer that has more
than one chiral centres and that is superimposable
on its mirror image because of the presence of an
internal plane of symmetry, hence it is optically
inactive (does not cause a rotation of plane-polarized
light)
Example : Tartaric acid , HOOCCH(OH)CH(OH)COOH
COOH COOH
P Q
H OH HO H
plane of symmetry
H OH HO H
COOH COOH
rotate 180o
COOH
identical
H OH
plane of symmetry
H OH
COOH
At first glance, P and Q are assumed to be enantiomers
It is a meso compound
COOH COOH
R S
H OH HO H
*not a plane of symmetry
OH H H OH
COOH COOH
rotate 180o
COOH
different
HO H
*not a plane of symmetry
H OH
COOH
R and S are related as mirror images and are not
superimposable even if rotated 180o
CH3 CHO
Cl H HO H
H OH plane of symmetry
Cl H HO H
CH3 CHO
11.6 REACTIONS OF ORGANIC COMPOUNDS
Homolytic cleavage
Heterolytic cleavage
a) Homolytic Cleavage
X • X X• + X • ≡ 2X•
•
free radicals
b) Heterolytic Cleavage
A •• - + B+ A is more
anion cation electronegative
A •• B
A+ + B •• - B is more
cation anion electronegative
Carbocations and free radicals are intermediates in
organic reactions.
a) Carbocation
(CH3)3C — Cl (CH3)3C+ + Cl-
carbocation anion
Example :
free radicals
uv
Cl – Cl Cl • + Cl •
C C C• + •C
H3C H • CH3 + •H
11.6.3 Relative Stabilities of
Carbocations and Free Radicals
Carbocation Stability:
H H R R
H C H < R C H < R C H < R
+ C R
+ + +
methyl primary secondary tertiary
cation (1°) (2°) (3°)
Increasing stability
Likewise, the stability of free radical increases as
more alkyl groups are attached to the carbon atom
with unpaired electron
H H R R
H C H < R C H < R C H < R C R
Increasing stability
11.6.4 Reagents and Sites of Organic Reactions
a) Electrophile (E+)
+ - + - + -
C=O C–X C – OH
carbonyl haloalkanes hydroxyl
compound
b) Nucleophile (Nu-)
• Addition
• Substitution
• Elimination
• Rearrangement
1.Addition reaction
Example :
room
CH3CH=CH2 + Br2 CH3CHBrCH2Br
temperature
electrophile
b) Nucleophilic Addition
Example :
O OH
H+ CN-
CH3 C CH 3 + HCN CH3 C CH3
+
CN
2. Substitution Reaction
Example :
uv light
CH3CH3 + Cl2 CH3CH2Cl + HCl
b) Electrophilic Substitution
Example :
Br Br
Fe
+ Br2 Br + HBr
catalyst
electrophile
c) Nucleophilic Substitution
Example :
CH3CH2Br + OH-(aq) CH3CH2OH + Br-(aq)
nucleophile
3. Elimination Reaction
Example :
Conc. H2SO4
CH3CH2OH CH2= CH2 + H2O
4. Rearrangement Reaction
Example :
H
H C C R
tautomerisme H C C R
H OH
H O