chapter 4 introduction of organic
TRANSCRIPT
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CHAPTER 11 :
INTRODUCTIONTO
ORGANIC CHEMISTRY
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CHAPTER 11 :CHAPTER 11 :
INTRODUCTION TOINTRODUCTION TOORGANIC CHEMISTRYORGANIC 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
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11.1 INTRODUCTION
Organic chemistry is the study ofcarbon compounds
Generally, the components of organic compound are :
C, H, O, N, S, X (halogen) and P
Carbon compounds constitute the central chemicals of
all things on this planet. Carbon compounds include
deoxyribonuicleic acids (DNAs) the giant molecules
that contain the genetic information for all living species
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Organic and Inorganic Compound
Organic compound Inorganic compound
were defined as
compounds that
could be obtained
from living
organisms
were those that
came from
nonliving sources
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Examples of organic compounds :-
CH4
methane
(a component of natural gas)
OCOCH3
COOH
CH3 CHCOOH
NH2
Methyl salicylic acid
(aspirin-a drug)
alanine
(amino acid-a protein component)
NCH3
CO2CH3
OCO
cocaine
(a pain killer)
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CH2 C
O
NH
O
S
N
COOH
penicillin (an antibiotic)
Cl CH Cl
CCl3
dichlorodiphenyltrichloroetane(DDT- a pesticide component)
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N OHN
4-hydroxyphenylazobenzene(a kind of dye)
Caffeine(found in coffee and tea)
N
N
O
CH3
C H3
N
N
C H3
O
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C NH2NH2
O
Urea(a component in urine,
also used as fertilizer)
Deoxyribonucleic acid (DNA)(carries genetic informationof living organisms)
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11.2 EMPIRICAL, MOLECULAR AND
STRUCTURAL FORMULAE
Empirical formula is the formula that shows the
simplest ratio of number ofelements present in a
molecule
Molecular formula is a formula that shows the
actual number ofatoms of each element in a
molecule. Example : C2H4 , C2H4O2
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Molecular formula = (empirical formula)n
where n is a whole number
therefore,
massformulaempiricalmassmolecularrelative
n =
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Example 1 :
If the relative molecular mass of a substance with empiricalformula CH2O is 60.0, what is the molecular formula of the
substance?
Solution :-
massformulaempiricalmassmolecularrelative
n =
0.160.20.12
0.60
= = 2
Molecular ormula = (empirical ormula)n
= (CH2
)2
= C2H
4
O2
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A sample of hydrocarbon contains 85.7 % carbon and
14.3 % hydrogen by mass. Its molar mass is 56.
Determine the empirical formula and molecular formula
of the compound.
Example 2 :
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Solution :-
Element C H
Mass (g) 85.7 14.3
Moles (n) 85.7
12.0
14.3
1.0
Smallest ratio 7.1427.142
= 1
14.437.142
= 2
= 7.142 = 14.3
@ Empirical formula = CH2n (empirical molar mass)= molar massn ( 12 x 1 + 1 x 2 ) = 56
n = 4Molecular formula = C4H8
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Structural formula is a formula that shows
how the atoms of a molecule are bonded to
one another
Representation of structural formula :-
a) CondensedStructure
b) ExpandedStructure
c) SkeletalStructure
d) 3-Dimensional formula
e) Ficher Projection
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The structural theory of organic chemistry
Two central premises are fundamental :
1.The atoms of the elements in organic compoundscan form a fixed number of bonds. The measureof this ability is called valence.
Carbon tetravalent (C atoms form 4 bonds)
Oxygen divalent
Hydrogen & halogens monovalent
C
Carbon atoms aretetrahedral
O
Oxygen atoms aredivalent
H Cl
Hydrogen and halogenatoms are monovalent
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2.A carbon atom can use one or more of itsvalences to form bonds to other carbon atoms
Carbon-carbon bonds
C C
Single bond
C C
Double bond
C C
Triple bond
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a) Condensed Structure
In condensed formulae all the hydrogen atoms
that are attached to a particular carbon are
usually written immediately after that carbon
In fully condensed formulae all atoms that are
attached to a carbon are written immediately
after that carbon
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Example :
C4H9ClCH3CHCH2CH3 or CH3CH(Cl)CH2CH3
Condensed structure
Cl
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b) Expanded Structure
Expanded structures indicate the way in which
the atoms are attached to each other and are not
representations of the actual shapes of the
molecules.
Example :
C4H9ClC C C C
H H
H H HCl
H H H H
Expanded structure
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c) Skeletal Structure
This structure shows only the carbon skeleton
The hydrogen atoms that are assumed to bepresent, are not written.
Other atoms such as O, Cl, N and etc. are shown
Example :
CH3CH(Cl)CH2CH3
Cl
=1.
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H2C CH 2
H2C CH 2
2.
=
CH2=CHCH2OH3. =OH
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Practice Exercise :
Rewrite each of the following structures using skeletalformula :-
O
CH3CH
2CH
2C CH
3
(CH3)
2CHCH
2CH
2CH(CH
3)CH
2CH
3
CH2= CHCH2CH2CH = CHCH3
O
CH3CH
2CH ( CH
3) CH
2C OH
1.
2.
3.
4.
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d) 3 - Dimensional formula(wedge - dashed wedge - wedge)
Describes how the atoms of a molecule are arrangedin space
Example :
C
Br
H
H
H(Bromoethane)
C
Br
H
H
H
C
H
BrH
H
C
H
H
B rH
Indication :-
bonds that lie in theplane of the pagebonds that lie behindthe plane
bonds that project out
of the plane of thepaper
OR OR
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e) Fischer Projection
Vertical lines represent bonds that project behindthe plane of paper
Horizontal lines represent bonds that project out of
the plane of paper
The intersection of vertical and horizontal linesrepresent a carbon atom, that is stereocentre
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Example :
2 butanol , CH3CH(OH)CH2CH3
CH3
HO
CH2
CH3
H
CH3
H
CH2
CH3
OHOR
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11.3 FUNCTIONAL GROUPS AND
HOMOLOGOUS SERIES
A functional group is an atom or group of
atoms in an organic molecule which characterizedthe molecule and enables the molecule to react
in specific ways (determines its chemical properties)
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Functional groups are important for three reasons :
1. They are the units by which we divide organiccompounds into classes
2.They are sites of chemical reaction; a particularfunctional group, in whatever compound it is found,undergoes the same types of chemical reactions
3.Functional groups serve as a basic for namingorganic compounds
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Homologous series is series of compoundswhere each member differs from the next member
by a constant CH2 unit (14 mass unit)
Members of a homologous series are calledhomologs
A homologous series has four features:
1. All the members of a particular homologous serieshave the same general formula.
Example : General formula of alcohol is CnH2n+1OH,where n=1, 2, 3 etc
For n=1 CH3OH (methanol)
For n=2 C2H5OH (ethanol)
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2. All the members of a particular homologous serieshave the same functional group. Thus, they have
the same chemical reactions and can be made bythe same general methods
Example : All alcohols contain OH group
they react with carboxylic acids to give esters
they can be prepared, for instance, by heatingdilute sodium hydroxide solution with an
appropriate alkyl halide
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3. The successive members of any homologous seriesdiffer by CH2
Example : For alcohol group.
The first few alcohols are :
CH3OH (methanol)
CH3CH2OH (ethanol)
CH3CH
2CH
2OH (propanol)
} The different by CH2} The different by CH2
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4. There is a trend in the physical properties of themembers of any homologous series.
As the molecules increase in size, there is agradual change in physical properties, e.g. theirboiling points increase
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Some important functional groups in organiccompounds :-
HomologousHomologous
SeriesSeries
FunctionalFunctional
GroupGroup
GeneralGeneral
FormulaFormula
IUPACIUPAC
nomenclaturenomenclature
PrefixPrefix-- --suffixsuffix
ExampleExample
alkanealkane nonenone CCnnHH2n+22n+2 --aneane CHCH44
methanemethane
alkenealkene C = CC = C
(double(double
bond)bond)
CCnnHH2n2n --eneene CHCH22=CH=CH22
etheneethene
alkynesalkynes CC || CC
(triple(triple
bond)bond)
CCnnHH2n2n--22 --yneyne CHCH || CHCH
ethyneethyne
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HomologousHomologous
SeriesSeries
FunctionalFunctional
GroupGroup
GeneralGeneral
FormulaFormula
IUPACIUPAC
nomenclaturenomenclature
PrefixPrefix-- --suffixsuffix
ExampleExample
arenearene CCnnHH2n2n--66 --benzenebenzene
alcoholalcohol OHOH
(hydroxyl)(hydroxyl)
CCnnHH2n+12n+1OHOH alkanolalkanol CHCH33CHCH22OHOH
ethanolethanol
etherether OROR(alkoxy)(alkoxy)
CCnnHH2n+22n+2OO alkoxyalkanealkoxyalkane CHCH33OCHOCH33methoxymethanemethoxymethane
haloalkanehaloalkane XX
(halogen)(halogen)
CCnnHH2n+12n+1XX haloalkanehaloalkane CHCH33CHCH22ClCl
chloroethanechloroethane
aromatic
ring
CH3
methylbenzene
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HomologousHomologous
SeriesSeries
FunctionalFunctional
GroupGroup
GeneralGeneral
FormulaFormula
IUPACIUPAC
nomenclaturenomenclature
PrefixPrefix-- --suffixsuffix
ExampleExample
aldehydealdehyde CCnnHH2n2nOO alkanalalkanal CHCH33C=OC=O
ketoneketone CCnnHH2n2nOO alkanonealkanone CHCH33C=OC=O
carboxyliccarboxylicacidacid
CnHCnH2n2nOO22 alkanoic acidalkanoic acid CHCH33C=OC=O
C
O
H
carbonylH
ethanal
C
O
carbonylCH3
propanone
C OH
O
carboxyl
OHethanoic
acid
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HomologousHomologous
SeriesSeries
FunctionalFunctional
GroupGroup
GeneralGeneral
FormulaFormula
IUPACIUPAC
nomenclaturenomenclature
PrefixPrefix-- --suffixsuffix
ExampleExample
acylacyl
chloridechloride
CCnnHH2n+12n+1
COClCOCl
alkanoylalkanoyl
chloridechloride
CHCH33C=OC=O
esterester CCnnHH2n2nOO22 alkylalkyl
alkanoatealkanoate
CHCH33COOCHCOOCH33
amideamide CCnnHH2n+12n+1
CONHCONH22
--amideamide CHCH33CONHCONH22
amineamine --NHNH22 CCnnHH2n+12n+1
NHNH22
--amineamine CHCH33NHNH22
C
O
Cl
acylCl
ethanoyl
chloride
C
O
O C
ester
C
O
NH2
ethyl
ethanoate
amideethanamide
amino methanamine
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11.4 CLASSIFICATION OF CARBON ANDHYDROGEN ATOMS IN ORGANIC
MOLECULES
Carbon atom classified primary (1o)
secondary (2o)
tertiary (3o)
quarternary (4o)
depending on the
number of carbonatoms bonded to it
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A primary carbon directly bonded to one other
carbon atom(has 1 adjacent carbon atom)
C
H
H
CH3
H
Example :
1o carbon
1oH
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A secondary carbon directly bonded to two other
carbon atoms(has 2 adjacent carbon atoms)
C
H
CH3
H CH3
Example :
2o carbon
2o H
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A tertiary carbon directly bonded to three other
carbon atoms(has 3 adjacent carbon atoms)
C
CH3
CH3
H CH3
Example :
3o carbon
3o H
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A quarternary carbon directly bonded to four other
carbon atoms(has 4 adjacent carbon atoms)
CCH3
CH3
CH3
CH3
Example :
4o carbon
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Similarly, a hydrogen atom is also classified as
primary, secondary or tertiary depending on the
type of carbon to which it is bonded.
1 hydrogen atom bonded to a 1 C atom
2 hydrogen atom bonded to a 2 C atom
3 hydrogen atom bonded to a 3 C atom
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Classification of haloalkanes (alkyl halides)
Alkyl halides are classified based on the carbon atom
to which the halogen is directly attached.
1 alkyl halide the halogen atom is bonded to a
primary carbon atom
2 alkyl halide the halogen atom is bonded to asecondary carbon atom
3 alkyl halide the halogen atom is bonded to atertiary carbon atom
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H C
H
H
C
H
H
Cl
H C
H
H
C
H
C
H
H
HCl
H C
H
H
C C
H
H
HCl
CH3
1 alkyl chloride
1 C
2 alkyl chloride
2 C
3 alkyl chloride
3 C
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Classification of alcohols
Alcohols are classified based on the carbon atom
to which the hydroxyl group is directly attached.
1 alcohol the hydroxyl group is attached to a
1 carbon atom
2 alcohol the hydroxyl group is attached to a2 carbon atom
3 alcohol the hydroxyl group is attached to a3 carbon atom
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H C
H
H
C
H
H
OH
H C
H
H
C
H
C
H
H
HOH
H C
H
H
C C
H
H
HOH
CH3
1 alcohol
1 C
2 C
2 alcohol
3 alcohol
3 C
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Classification of amines
Amines are classified based on the number of alkylgroups or carbon atoms that are directly attached
to the nitrogen atom
1 amine N is bonded to one alkyl group
2 amine N is bonded to two alkyl groups
3
amine N is bonded to three alkyl groups
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H3
C N
H
H
H3
C N H
CH3
H3C N
CH3
CH3
N bonded toone alkyl group
A primary (1)amine
N bonded totwo alkyl group
A secondary (2)amine
N bonded to three
alkyl group
A tertiary (3)amine
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ISOMERISM
Structural/Constitutional Isomerism Stereoisomerism
Isomerism
Chainisomerism
Positionalisomerism
Functionalgroup
isomerism
Geometricisomerism
Opticalisomerism
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Isomerism is the existence of different compounds
with the same molecular formula but different
structural formulae
Isomers different compounds that have same
molecular formula
Two types ofisomerism
structural isomerism
stereoisomerism
different order of attachmentof atoms
different spatial arrangement of
atoms in molecules
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Structural isomerism
Chain/skeletal
isomerism
Structural isomers are different compounds with
the same molecular formula but differ in the order
of attachment of atoms
Positional
isomerism
Functional
groupisomerism
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The isomers differ in the carbon skeleton(different carbon chain)
a) Chain/skeletal isomerism
They possess the same functional group andbelong to the same homologous series
Example :
C5H12 :
CH3CH2CH2CH2CH3
CH3CHCH2CH3
CH3
CH3-C-CH3
CH3
CH3
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1,2-dimethylbenzene
iii) C8H10 CH3CH3
CH3
CH3
1,3-dimethylbenzene
CH3
CH3
1,4-dimethylbenzene
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c) Functional group isomerism
These isomers have different functional groups
and belong to different homologous series withthe same general formula
Different classes of compounds that exhibit
functional group isomerism :-
General formulaGeneral formula Classes of compoundsClasses of compounds
CnH2n+2O alcohol and ether
CnH2nO aldehyde and ketone
CnH2n alkene and cycloalkane
CnH2nO2 carboxylic acid and ester
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Example :
i) C2H6O CH3CH2OH
ethanol
CH3OCH3
dimethyl ether
ii) C3H6O CH3CH2C-H
O
propanal
CH3C-CH3
O
propanone
iii) C3H6O2 CH3CH2C-OH
O
propanoic acid
CH3C-O-CH3
O
methyl ethanoate
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Stereoisomerism
Geometric Isomerism Optical Isomerism
a) Geometric isomerism
occurs only in two classes of compounds :
Alkenes & cyclic compound
(because of rigidity in molecules)
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Geometric isomers (also called cis-trans isomers)
are stereoisomers that differ by groups being
on the same side (cis-isomer) or opposite
sides (trans-isomer) of a site of rigidity in a molecule
The requirements for geometric isomerism :
i) restricted rotation about a C=C,double bond, inalkenes or a C-C single bond in cyclic compounds
ii) each carbon atom of a site of restricted rotation hastwo different groups attached to it
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Examples :
H3C CH3
H H
C C=
i)
cis-2-butene
H3C
C=C
CH3
H
H
trans-2-butene
ii) H3C CH2CH3
C= C
H CH3
trans-3-methyl-2-pentene
H3C CH3
C= CH CH2CH3
cis-3-methyl-2-pentene
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iii)
HH
CH3 CH3
cis-1,2-dimethylcyclohexane
H
HCH3
CH3
trans-1,2-dimethylcyclohexane
Cl
Cl
H
H
iv)
Cl
Cl
H
H
cis-1,3-dichlorocyclopentane trans-1,3-dichlorocyclopentane
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If one of the doubly bonded carbons has 2 identical
groups, geometric isomerism is not possible.
Examples :
CH3CH2i)
C = C
H
HH3C
2-methyl-2-butene
Hii)
C= C
CH3
CH3Cl
1-chloro-2-methylpropene
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cis-trans isomers have similar chemical properties
but different physical properties
They differ in melting and boiling points and
solubility due to different polarity of the molecules
cis-isomers polar molecules
trans-isomers non-polar
Melting point: trans- isomer > cis-isomer Boiling point: cis-isomer > trans- isomer
Stability: trans-isomer > cis-isomer
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b) Optical isomerism
If a beam of light is passed through a piece of
polarizer prism, the emergent light vibrates in a
single plane, hence it is called aplane-polarized
light
Opticallyactive compounds have the ability to
rotate plane-polarized light
The angle of rotation can be measured with an
instrument called polarimeter
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Schematic representation of a polarimeter containingan optically active sample :
clockwise rotation plus sign (+) / dextrorotarory
anticlockwise rotation minus sign (-) / levorotorary
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The requirements for optical isomerism :-
i) molecule contains a chiral carbon or chiral centre(carbon atom with 4 different groups attached to it)
ii) molecule is not superimposable with its mirror image
A representation of a chiral molecule with
3-dimensional formula :-
P
CQ
R
S* P{Q{R{S
*designates chiral centre
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Enantiomers are apair of mirror-image molecules
that are notsuperimposable (must have one or more
chiral carbons)
Examples :
i) 2-butanol, CH3CHCH2CH3
OH
C*
CH2CH3
H3C
OHH
C
CH2CH3
CH3HOH
enantiomers
:-
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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 others rotation)
A pair of enantiomers have identical chemical and
physical properties but differ in the direction of
rotation of plane-polarized light
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A compound with n chiral centers can have a
maximum of2n stereoisomers
If a molecule contains two or more chiral centers,
diastereomers may exist
Diastereomers are stereoisomers that are not
mirror images of each other
All physical properties of diastereomers are usually
different from one another
Example :
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Example :
The 4 stereoisomers of 2-amino-3-hydroxybutanoicacid CH3CH-CHCOOH are shown below using
OH NH2Fischer projection formula:-
COOH COOH
CH3 CH3
HH
HH
NH2 H2NOH HO
enantiomers
COOH
NH2H
H
HO
CH3
COOH
H
H
OH
H2N
enantiomers
CH3
A B
C D
Four pairs ofdiastereomersare identified :
A and C;A and D ;B and C;B and D
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Meso compoundis a stereoisomer that has more
than one chiral centres and that issuperimposableon its mirror image because of the presence of an
internal plane ofsymmetry, hence it is optically
inactive (does not cause a rotation of plane-polarizedlight)
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Example : Tartaric acid , HOOCCH(OH)CH(OH)COOH
COOH
OH
OH
H
H
COOH
COOH
COOH
HO
HO
H
H
COOH
COOH
H
H
OH
OH
plane of symmetry
plane of symmetry
rotate 180o
P Q
identical
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At first glance, Pand Q are assumed to be enantiomers
But if compound Q is rotated 180o in the plane ofthe paper, it is actually identical to compound P,therefore Pand Q are superimposable mirror images
Pand Q are thesame compound
It is a meso compound
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COOH
OH
OH
H
H
COOH
COOH
COOH
R S
COOH
COOH
HHO
H OH*not a plane of symmetry
*not a plane of symmetry
rotate 180o
different
H OH
HHO
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R and S are related as mirror images and are notsuperimposable even if rotated 180o
Thus R and Sconstitute an enantiomeric pair
There are 2 pairs of diastereomers :
Pand R & Pand S
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Further examples of meso compounds:
CH3
CH3
Cl
Cl
H
H
CHO
CHO
HO
HO
H
HH OH plane of symmetry
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11.6 REACTIONS OF ORGANIC COMPOUNDS
11.6.1 Types of CovalentBond Cleavage/Fission
All chemical reactions involved bond breaking andbond making
Two types of covalent bond cleavage :-
Homolytic cleavage
Heterolytic cleavage
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a) Homolytic Cleavage
Occurs in a non-polar bond involving two atoms of
similar electronegativity
A single bond breaks symmetrically into two equal
parts, leaving each atom with one unpaired electron
Free radicals are formed in homolytic cleavage
X X X + X 2X
free radicals
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b) Heterolytic Cleavage
Occurs in a polar bond involving unequal sharingof electron pair between two atoms of differentelectronegativities
A single bond breaks unsymmetrically and both the
bonding electrons are transferred to the moreelectronegative atom
Cation and anion are formed in heterolytic cleavage
A BA
-
+ B+
A is moreelectronegative
A+ + B- B is more
electronegative
cationanion
anioncation
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Carbocations and free radicals are intermediates inorganic reactions.
They are unstable and highly reactive
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11.6.2 Reaction Intermediates
a) Carbocation
Also called carbonium ion
A very reactive species with apositive charge
on a carbon atom
Carbocation is formed in heterolytic cleavage
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Example :
(CH3)3C ClH H
(CH3)3C+
carbocation
+ Cl-
anion
Chlorine is more electronegative than carbon andthe CCl bond is polar
The CCl bond breaks heterolitically and both thebonding electrons are transferred to chlorine atomto form anion and carbocation
b) F R di l
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b) Free Radical
A very reactive species with an unpaired electron
Formed in homolytic cleavage
Cl Cl
Example :
uv Cl
free radicals
+ Cl
C C C + C
H3C H CH3 + H
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11.6.3 Relative Stabilities ofCarbocations and Free Radicals
Carbocation and free radical primary
secondary
tertiary
depending on the number of carbon atoms directlybonded to the :-
positively charged carbon atom (for carbocation)
carbon atom with unpaired electron (for free radical)
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The stability of carbocation increases with thenumber of alkyl groups present
The alkyl groups are electron-releasing relative tohydrogen, thus help to stabilize the positive chargeon the carbocation
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Lik i h bili f f di l i
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Likewise, the stability of free radical increases asmore alkyl groups are attached to the carbon atomwith unpaired electron
Free RadicalStability :
H C H < R C H < R C H < R C R
H H RR
methylradical primary(1) secondary(2) tertiary(3)
Increasing stability
11 6 4 Reagents and Sites of Organic Reactions
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11.6.4 Reagents andSites of OrganicReactions
a) Elec trophile (E+
)
Means electron loving
An electron-deficientspecies and electron-pair
acceptorthat attacks a part of a molecule wherethe electron density is high
An electrophile can be either neutralorpositivelycharged
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Examples of electrophiles :-
1.cations such as H+, H3
O+, NO2+, Br+ etc.2.carbocations.3.Lewis acids such as AlCl3, BF3 etc.4.oxidizing agents such as Cl2, Br2 and etc
Examples of electrophilic sites in organic molecules :-
molecules with low electron density around apolar bond such as :-
H+ H- H+ H- H+ H-C = O C X C OH
carbonyl haloalkanes hydroxyl
compound
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b) Nucleophile (Nu-)
Means nucleus loving
An electron-rich species and electron-pair donorthat attacks a part of a molecule where the electron
density is low
A nucleophile can be either neutralor negativelycharged
E l f l hil
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Examples of nucleophiles :-
1. anions such as OH-
, RO-
, Cl-
, Cn-
etc.2. carbanions. (species with ve charge on C atoms)3. Lewis bases which can donate lone pair electrons
such as NH3, H2O etc.
Examples of nucleophilic sites in organic molecules :-
molecules with high electron densityaround thecarbon-carbon multiple bond such as :-
-C=C- (alkenes) , -C|C-(alkynes),
(benzene ring) and etc.
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11.6.5 Types of OrganicReactions
The four main types of organic reactions are:
Addition
Substitution
Elimination
Rearrangement
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a) ElectrophilicAddition
Initiated by an electrophile, which attacks anucleophilic site of a molecule
Typical reaction of unsaturated compounds suchas alkenes and alkynes
Example :
CH3
CH=CH2
+ Br2
CH3
CHBrCH2
Brroom
temperature
electrophile
b) l hili ddi i
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b) NucleophilicAddition
Initiated by a nucleophile, which attacks anelectrophilic site of a molecule
Typical reaction ofcarbonyl compounds
Example :
CH3 C CH 3 + HCN
O
CH3 C CH3
OH
CN
H
H+
H+ CN-
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2. Substitution Reaction
A reaction in which an atom orgroup in a molecule is replacedby
another atom or group
a) Free-radicalSubstitution
b) ElectrophilicSubstitution
c) NucleophilicSubstitution
) F di l S b tit ti
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a) Free-radicalSubstitution
Substitution which involves free radicals asintermediate species
Example :
CH3CH3 + Cl2 CH3CH2Cl + HCluv light
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b) ElectrophilicSubstitution
Typical reaction ofaromatic compounds
The aromatic nucleus has high electron density,thus it is nucleophilic and is tend to electrophilic
attack
Example :
+ Br2Fe
catalystBr + HBr
electrophile
BrH
BrH
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c) NucleophilicSubstitution
Typical reaction of saturated organic compoundsbearing polar bond as functional group, such ashaloalkane and alchohol
Example :
CH3CH2Br + OH-(aq) CH3CH2OH + Br
-(aq)
nucleophile
HH
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3. Elimination Reaction
A reaction in which atoms or groups are removedfrom adjacent carbon atoms of a molecule to forma multiple bond(double or triple bond)
E
limination reaction results in the formation ofunsaturated molecules
CH3CH2OH CH2= CH2 + H2OConc. H2SO4
(
Example :
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