substitution

1
esterification
oxidation
oxidation
elimination
Cr2O72- / H(aq) / reflux
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
addition
H2(g)/Ni 150?C 5 atm
acylation
substitution
substitution
hydrolysis
acylation
substitution
Br2(l) sunlight
R1NH2 room temp
c. NH3(aq) heat in a sealed tube
H(aq)/H2O reflux
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 RCHCHR1 and its subsequent
oxidation to the ketone.