Mechanism Summary for AS AQA Chemistry

Nucleophilic Substitution of Haloalkanes

Nucleophilic Substitution of Haloalkanes

with aqueous hydroxide ions.

H

with cyanide ions.

H

H3C

-HO:

Br

H3C

H3C

OH + :Br -

-NC:

Br

H3C

CN + :Br

Nucleophilic Substitution of Haloalkanes with ammonia

H
CH3 CH2

+
C

3HN:

Br

CH3 CH2 C

Elimination of Haloalkanes with ethanolic

hydroxide ions

:Br -

CH3 C

:NH3
Br

CH3 C

+ Br - + H2O

H
CH3 CH2 C

:OHNH2 + NH Br
4

Electrophilic Addition of Alkenes with hydrogen

bromide

Electrophilic Addition of Alkenes with Bromine

H

H
C

Br

Br +
Br

:Br

Br

Br

H3C

CH3

H3C

:Br -

Electrophilic Addition of Alkenes with sulphuric acid

H3C

CH3

Br

H3C

H3C

Br

H
C

Free Radical Substitution of Alkanes with Bromine

+
H

-:OSO

OSO 2OH
H3C

CH3

2OH

STEP ONE Initiation

Essential condition: UV light
Br2
2Br

STEP TWO Propagation

H
OSO 2OH

CH3CH3 + Br
HBr + CH3CH2

CH3CH2 + Br2
CH3CH2Br + Br

STEP THREE Termination

CH3CH2 + Br
CH3CH2Br

CH3CH2 + CH3CH2
CH3CH2CH2CH3

N Goalby

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diol
poly(alkene)

KOH aqueous
heat under reflux
nucleophilic substitution

high pressure
catalyst

dihaloalkane

alkene
alkane
1 H2SO4
2 H2O warm
Electrophilic
Addition

conc H2SO4 or
conc H3PO4
Elimination

alcohol

Br2, Cl2 UV light

Free radical
Substitution

KOH aqueous
heat under reflux
nucleophilic substitution

haloalkane

KCN in alcohol
heat under reflux
nucleophilic substitution

nitrile

aldehyde

ketone

If primary alcohol or aldehyde

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

carboxylic acid
N Goalby

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Alcoholic NH3
heat under pressure
nucleophilic substitution

amine