An organic compound ( A ) has characteristic odour. On treatment with NaOH, it forms compounds ( B ) and ( C ). Compound ( B ) has molecular formula C7H 8Owhich on oxidation gives back ( A ). The compound ( C ) is a sodium salt of an acid. When ( C ) is treated with soda-lime, it yields an aromatic compound ( D ). Deduce the structures of ( A ), ( B ), ( C ) and ( D ). Write the sequence of reactions involved.
• The molecular formula of ( B ) C7H8O indicates that it might be bezyl alcohol 
, and C which is a sodium salt of an acid is Na salt of benzoic acid which is 
which on reaction with sodalime i.e. a mixture of (CaO+NaOH) gives benzene 
which is compound ( D ) . and from all the summed up informations the parent compound ( A ) with a characteristic odour should be benzaldehyde 
.
• The first step-this is basically a cannizaro reaction of benzaldehyde which undergoes self-oxidation and reduction (i.e. disproportionation) on reaction with strong alkali NaOH and produces 
on reduction and 
on oxidation.
• Next bezyl alcohol on oxidation gives 
back.
• And 
on reaction with sodalime gives 
which is an aromatic compound.
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