CHEMISTRY

Advanced Subsidiary Level - 2015

Unit 02 :

ORGANIC MECHANISMS

Dimuthu Sandaruwan
Acquire Institute, Negombo

Mechanisms required:
1.free radical substitution

-methane with chlorine

2. electrophilic addition -alkenes with hydrogen bromide

-alkenes with bromine
-alkenes with sulphuric acid
3. nucleophilic substitution

4. elimination

-haloalkanes with hydroxide ions

-haloalkanes with cyanide ions
-haloalkanes with ammonia

-hydrogen halides from haloalkanes

Remember:All curly arrows must originate from a lone pair or a bond

The lone pair must be shown
All free radicals must be shown clearly with a dot

Breaking of bonds

Homolytic bond breaking

Heterolytic bond ssion

Page 01

Mechanism of Chlorination of methane

Cl - Cl

Iniciation

2Cl

- -

H-C-H

Cl

CH3 + HCl

CH3

Cl - Cl

CH3Cl + Cl

- -

Cl

H-C-H

Cl

CH2Cl + HCl

Propergation
CH2Cl

Cl - Cl

CH2Cl2 + Cl

- -

Cl

H-C-H

Cl

CHCl2 + HCl

Cl
CHCl2

Cl - Cl

CHCl3 + Cl

- -

Cl

Cl-C-H

Cl

CCl3

+ HCl

Cl - Cl

CCl4

+ Cl

Cl
CCl3

Termination

CH3

Cl

CH3Cl

CH3

CH3

CH3CH3

CH3

CHCl2

CH3CHCl2

Page 02

Electrophilic Addition reaction

H-C-C-H

+ HX

- -

C-C

- -

01). Alkenes with Hydrogen Bromide

- -

- -

- -

Br

H-C-C-H

H-C-C-H

C-C

Mechanism

Br

Br -

- -

- -

Br - Br

Br

- -

Br
H
C -C
H
H
H

Mechanism
H
H
C

- -

H-C-C-H

+ X2

C-C

H-C-C-H

02). Alkenes with Bromine

Br H

Br

OH

H-C-C-H

+ H2SO4

- -

-C
C-

- -

03). Alkenes with Sulphuric Acid

H-C-C-O
H H

- -

+ -H

- -

H-C-C-H

- -

H2SO4

- -

- -

Mechanism
H-C-C-O- H
H H

HSO4

Page 03

Nucleophilic Substitution Reactions

04). haloalkanes with hydroxide ions

OH-

Mechanism

CH3CH2- OH

- -

- -

H-C-C-X

- -

- -

CH3CH2-Br

H-C-C-OH

OH-

05). haloalkanes with cyanide ions

H-C-C-X

CN

- -

CH3CH2- CN + X

- -

Mechanism

CN-

- -

- -

CH3CH2-X

H-C-C-CN

06). haloalkanes with ammonia

Page 04