esterification

oxidation oxidation
elimination
R1OH / c.H2SO4 catalyst O
R H O O
Cr2O72- / H+(aq) / reflux Cr2O72- / H+(aq)
C C Al2O3(s) / 300C R C R C reflux R C
R CH2 OH
H reflux OH
H H or c.H2SO4 / reflux H (aq) / H2O
+
O R1
alcohol NaBH4
alkene followed by H2O aldehyde carboxylic acid ester
reduction hydrolysis

substitution substitution
acylation
HBr(aq) NaOH(aq) NaBr(s) / c.H2SO4 substitution
room temp reflux R1OH
reflux
room temp
addition SCl2O
reflux

NaCN in aqueous O O
addition
ethanol solution c.NH3(aq)
R CH2 Br R CH2 CN R C R C
halogenoalkane reflux nitrile Cl room temp NH2
H2(g)/Ni acyl chloride acylation primary amide
substitution
150C
5 atm substitution
hydrolysis
acylation
Br2(l) substitution
sunlight R1NH2
c. NH3(aq) H+(aq)/H2O
room temp
heat in a sealed tube reflux
O
R CH3 R CH2 NH 2 R CH2 COOH R C
alkane amine carboxylic acid
(reacts as above) 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.
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.