1. NaCN in aqueous ethanol solution
esterification
oxidation
oxidation
elimination
R1OH / c.H2SO4 catalyst
reflux
ester
alkene
Cr2O72- / H+(aq) / reflux
aldehyde
Cr2O72- / H+(aq)
reflux
carboxylic acid
Al2O3(s) / 300C
or c.H2SO4 / reflux
followed by H2O
alcohol
H+(aq) / H2O
NaBH4
reduction
hydrolysis
substitution
substitution
acylation
HBr(aq)
room temp
NaOH(aq)
reflux
NaBr(s) / c.H2SO4
reflux
substitution
R1OH
room temp
addition
SCl2O
reflux
NaCN in aqueous ethanol solution
reflux
addition
acyl chloride
primary amide
c.NH3(aq)
room temp
halogenoalkane
nitrile
H2(g)/Ni
150C
5 atm
substitution
acylation
substitution
hydrolysis
acylation
Br2(l)
sunlight
substitution
R1NH2
room temp
c. NH3(aq)
heat in a sealed tube
H+(aq)/H2O
reflux
secondary amine
alkane
amine
carboxylic acid
(reacts as above)
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.
2. The halogenoalkane shown will only be a minor product of the reaction from the alkene.
The main product will be the isomer with the Br 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 alcohol from an alkene RCH=CHR1 and its subsequent oxidation to the ketone.