Mechanism Summary for AS AQA Chemistry

Nucleophilic Substitution of halogenoalkanes Nucleophilic Substitution of halogenoalkanes

with aqueous hydroxide ions. with cyanide ions.
H H H H
δ+
δ- δ+ δ- -
H3C C Br H3C C OH + :Br - H 3C C Br H 3C C CN + :Br
- -
NC:
HO: H
H H H

Nucleophilic Substitution of halogenoalkanes with ammonia

Elimination of halogenoalkanes with ethanolic
H H H :Br -
hydroxide ions
δ+ δ- +
CH3 CH2 C Br CH3 CH2 C N H H H H H
3HN:
H H CH3 C C H CH3 C C H
H
:NH3
+ Br - + H2O
Br H
H :OH-
CH3 CH2 C NH2 + NH Br
4

Electrophilic Addition of alkenes with bromine Electrophilic Addition of alkenes with hydrogen
bromide
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 Br Br δ+
Br δ+ H H
:Br - δ- :Br -
Br
Br δ-
H H

Electrophilic Addition of alkenes with sulfuric acid H3C C C CH3

H H Br H
H H
+
H3C C C H H3C C C H
δ+ H Free Radical Substitution of alkanes with bromine
H -
:OSO2OH
OSO 2OH STEP ONE Initiation
δ- Essential condition: UV light
H H
Br2  2Br
.
H3C C C H
H STEP TWO Propagation
OSO 2OH .
CH3CH3 + Br  HBr + CH3CH2
.
.
CH3CH2 + Br2  CH3CH2Br + Br
.

STEP THREE Termination

.
CH3CH2 + Br  CH3CH2Br
.
.
CH3CH2 + CH3CH2  CH3CH2CH2CH3
.
Acid catalysed elimination mechanism: alcohols alkenes
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
The H+ comes from the conc H2SO4 or conc H3PO4

Acid catalysed addition mechanism for hydration of ethene

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 H+
O
H+ H H
H
The H+ comes from the conc H3PO4
AS Reactions- Summary
diol
poly(alkene) KOH aqueous
heat under reflux
nucleophilic substitution
high pressure
catalyst
dihalogenoalkane
alkene

alkane
1 H2SO4
conc H2SO4 or 2 H2O warm
conc H3PO4 Electrophilic
Acid catalysed Br2, Cl2 UV light
Addition
Free radical
Elimination
Substitution

KOH aqueous
heat under reflux
alcohol nucleophilic substitution halogenoalkane
KCN in ethanol/ water Alcoholic NH3
mixture heat under reflux heat under pressure
nucleophilic substitution nucleophilic substitution

nitrile amine

aldehyde ketone

If primary alcohol or aldehyde

K2Cr2O7/H+
heat under reflux
+ excess oxidising agent
Oxidation

carboxylic acid