Mechanism Summary for A-level AQA Chemistry

H H H H H H H H
H H
+
C C H C C H H C C H H3C C C CH3 +
H3C C C CH3
H H Br δ+
Br δ+ Br Br H H
:Br - δ- :Br -
Br δ- Br
H H

H3C C C CH3

H H H H Br H
+
H3C C C H H3C C C H
δ+ H
H -:OSO
2OH H H H H
OSO 2OH
δ- CH3 C C H
H H CH3 C C H

H3C C C H Br H
H :OH-
OSO 2OH

H
H H H H H
H3C C CH3 CH3 +
H3C C H C C CH3 H C C CH3

O H +
O H H
:

H H H H H H
H H
+
H C C H H C C H H C C H
C C
+
H H H H H O H H O
O
H H
H

H H STEP ONE Initiation

δ+ δ- Essential condition: UV light
H3C C Br H3C C OH + :Br -
Br2 2Br
.
-HO:
H H
STEP TWO Propagation
CH3CH3 + Br
. HBr + CH3CH2
.

CH3CH2 + Br2
. CH3CH2Br + Br
.
H H
δ+ δ- STEP THREE Termination
H 3C C Br H 3C C CN + :Br -
CH3CH2 + Br
. . CH3CH2Br
-NC:
H H
CH3CH2 + CH3CH2
. . CH3CH2CH2CH3
Reaction 1 with ammonia forming primary amine

H H
+
H3C C Br H3C C NH3 Br -
H
H
3HN:

H H
+
H3C C NH2 H3C C NH2 + NH4Br
:NH3
H H H

Reaction 2 forming secondary amine

The amine formed in the first reaction has a lone pair of electrons on the
nitrogen and will react further with the haloalkane.
H
+
H3C C Br H3C CH2 NH2 CH2 CH3 Br -
H
:

CH3CH2NH2
+
H3C CH2 NH CH2 CH3 H3C CH2 NH CH2 CH3 + NH4Br
:NH3
Diethylamine
H

Reaction 3 forming a tertiary amine

H CH3
CH2
H3C C Br +
H3C CH2 NH CH2 CH3
H
:

H3C CH2 NH CH2 CH3

CH3
CH2 CH3
+ CH2
H3C CH2 N CH2 CH3
:NH3 H3C CH2 N CH2 CH3
H triethylamine

Reaction 4 forming a quaternary ammonium salt

H

H3C C Br CH3
CH2
H +
H3C CH2 N CH2 CH3
:

H3C CH2 N CH2 CH3 CH2

CH2 CH3
CH3 Tetraethylammonium ion
 Mechanism Summary for A-Level AQA Chemistry

Nucleophilic Addition Mechanism Nucleophilic Addition Mechanism

H+ from water or weak acid
O
δ-
O:
- H+ δ-
H+ from sulphuric acid
O
O:
- H+
δ+
C H3C C CH3
+
H3C CH3 Cδ H3C C CH3
H
:H- H3C CH3
CN
O H :CN- O H
H3C C CH3 H3C C CH3
H CN

Nucleophilic Addition –Elimination Mechanism Nucleophilic Addition –Elimination Mechanism

O δ- :O- δ- :O
-
O
CH3 C δ+ + +
H3C C OH CH3 C δ+
H3C C OCH2CH3
Cl Cl
:OH Cl H
Cl H
: OCH CH
O 2 3
H O
CH3 C H
C
OH H3C OCH2CH3

Nucleophilic Addition –Elimination Mechanism Nucleophilic Addition –Elimination Mechanism

δ- : O- δ-
O : O-
O
+ CH3 Cδ+ +
CH3 C δ+ H3C C NH2 H3C C NHCH2CH3
Cl
Cl Cl H :NHCH CH Cl H
: NH3 O
2 3
O
H
C C
H3C NH2 H3C NHCH2CH3

Electrophilic Substitution Electrophilic Substitution

Equation for Formation of electrophile Equation for Formation of the electrophile.
HNO3 + 2H2SO4 NO2+ + 2HSO4- + H3O+ AlCl3 + CH3COCl CH3CO+ AlCl4-

NO 2 O O
+ C CH3
H C CH3
H

NO 2 O
C
+ H+ CH3

H+ + HSO4- H2SO4
Reaction Summary for A-level AQA Chemistry

Nu Add
Nu Add

NuSub
NuSub

NuSub

Nu Add

Esters and
amides can be
hydrolysed by
NaOH and acids

ester
 Aromatic synthetic routes

NO2
conc nitric acid + NH2
conc sulphuric acid
NH CH3
Sn and HCl CH3Cl
reduction Nu sub
Electrophilic
substitution

CH3COCl
acyl chloride in the presence Nucleophilic add-el
of anhydrous aluminium
chloride catalyst
Electrophilic substitution O
NH C CH3
O H
C O
CH3
C CN
Nu Add
CH3

Nu Add
H
O
OH
CH
CH3 C CH2 NH2

CH3

O
H3C CH O C CH3