esterification

elimination
R C H C H H

oxidation Cr2O72- / H+(aq) / reflux
R CH 2 OH R C H O

oxidation Cr2O72- / H+(aq) reflux
R C OH O

R1OH / c.H2SO4 catalyst reflux H+(aq) / H2O hydrolysis
R C

O

Al2O3(s) / 300rC or c.H2SO4 / reflux followed by H2O

alkene

alcohol

NaBH4 reduction

O

aldehyde

carboxylic acid

R1

ester

substitution HBr(aq) room temp addition NaOH(aq) reflux

substitution acylation NaBr(s) / c.H2SO4 reflux substitution SCl2O reflux NaCN in aqueous ethanol solution reflux substitution R1OH room temp

addition R CH 2

O
R

O

Br

halogenoalkane H2(g)/Ni 150rC 5 atm

nitrile

CH 2

CN

R

C

c.NH3(aq) room temp acylation

R

C NH2

Cl acyl chloride
hydrolysis

primary amide

substitution Br2(l) sunlight substitution c. NH3(aq) heat in a sealed tube
R CH2 NH2 R CH 2

acylation R1NH2 room temp
O

H+(aq)/H2O reflux
COOH

R CH3 alkane

amine

carboxylic acid (reacts as above)

R

C NH R1

secondary amine

Notes:

1.

The formation of a nitrile from a halogenoalkane is a carbon-carbon bond forming reaction. The carboxylic acid formed from the nitrile has an extra carbon atom in the side-chain. All the other reactions are simple functional group interconversions.

.

The halogenoalkane shown will only be a minor product of the reaction from the alkene. The main product will be the isomer with the r atom attached to the second carbon atom.
 

3.

You may wish to add other reactions to this toolkit. For example the formation of a secondary = and its subsequent oxidation to the ketone. alcohol from an alkene

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