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Nitrile function
to increase carbon chain length
haloalkane
NUCLEOPHILIC SUBSTITUTION
Haloalkane + KCN —> nitrile
normal nucleophilic substitution.
aldehyde
NUCLEOPHILIC ADDITION
aldehyde + NaCN + H2SO4 —> hydroxynitrile
ketone
NUCLEOPHILIC ADDITION
ketone + NaCN + H2SO4 —> hydroxynitrile