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ORGANIC
COMPOUNDS
Lecture 7
12.5 Reactions of Organic
Compounds
Learning Outcomes:
At the end of the lesson the students
should be able to :
Explain covalent bond cleavage:
homolytic
heterolytic
Types of Covalent Bond
Cleavage/Fission
X : X
X• + X•
free radicals
X• •X
b) Heterolytic cleavage
A + + B: -
cation anion
B is more
electronegative.
Reaction Intermediates
a) Carbocation
b) Carbanion
c) Free Radical
C C ●C + ●C
iii)
H3C H H3C ● + ●H
Lecture 7
12.5 Reactions of Organic
Compounds
Learning Outcomes:
At the end of the lesson the students
should be able to:
State the relative stabilities of primary,
secondary and tertiary free radicals,
carbocations and carbanions.
Explain the inductive effect of alkyl group
towards the stability of carbocations and
carbanions.
Define electrophile and nucleophile.
Relative Stabilities of Carbocations,
Carbanions and Free Radicals
H H R R
H C H < H C R <H C R < R C R
+ + + +
Methyl Primary Secondary Tertiary
cation 10 20 30
Increasing stability
Carbanion Stability
H H R R
H C H < H C R < H C R < R C R
- - - -
Methyl Primary Secondary Tertiary
anion 10 20 30
Increasing stability
Free-radical stability
Increasing stability
Reagents and sites of organic
reactions
A) Electrophile
Means ‘electron loving’.
An electron-deficient species and
accepting electron from an attacking
nucleophile.
Can be either neutral or positively
charged
Examples of electrophiles :
cations such as H+, H3O+, NO2+ etc.
carbocations.
Lewis acids such as AlCl3, FeCl3, BF3 etc.
oxidizing agents such as Cl2, Br2 and etc.
electrophilic sites are molecules with
low electron density around a polar bond
Examples:
i) δ + δ - ii)
δ + δ -
-C = O (carbonyl) ; -C – X (haloalkanes)
iii)δ+ δ -
-C – OH (hydroxy compounds)
b) Nucleophile
means ‘nucleus loving’
An electron-rich species and
electron-pair donor.
A nucleophile can be either neutral
or negatively charged.
Examples of nucleophiles :
a) Electrophilic Addition
b) Nucleophilic Addition
a)Electrophilic Addition
Initiated by an electrophile accepting
electron from an attacking nucleophile.
Typical reaction of unsaturated compounds
such as alkenes and alkynes.
Example :
Initiated
by a nucleophile, which
attacks an electrophilic site of a
molecule.
– Typical reaction of carbonyl compounds.
O CN
δ −
CH3 C CH3 + HCN CH3 C CH3
δ +
OH
II) Substitution Reaction
A reaction in which an atom or group in
a molecule is replaced by another atom
or group.
+ Br2 Fe Br + HBr
catalyst
electrophile
c) Nucleophilic Substitution
Typical reaction of saturated organic
compounds bearing polar bond as functional
group, such as haloalkane with alcohol.
Example :
δ +δ −
CH3CH2Br + OH-(aq) Δ CH3CH2OH + Br-(aq)
nucleophile
III) Elimination Reaction
– An atoms or groups are removed from
adjacent carbon atoms of a molecule to form
a multiple bond (double or triple bond).
– Results in the formation of unsaturated
molecules.
– Example :
Example : H
tautomerisme
H C C R H C C R
H OH H O
Exercises