f Mechanism Summary for A-level AQA Chemistry

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HE

H H H H H H H H
r H H
+
2504 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 #"
 mmmmm
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


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H
H H H H H
H3C C CH3 CH3 +
H3C C H C C CH3 H C C CH3
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 alllene alcohol

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 
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 H H
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 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
.

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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
 
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$)&-2&6*3&/2( 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

Oδ
- :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 
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 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
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Nu Add
CH3
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CH3

  

 
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H3C CH O C CH3


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