JEE MainChemistryAldehydes and Ketones
An unknown nitrile A reacts with phenylmagnesium bromide in the presence of dry ether, followed by acidic hydrolysis, to form an intermediate ketone P . Ketone P is then subjected to Clemmensen reduction using Zn-Hg and concentrated HCl to yield n-propylbenzene. The IUPAC name of the starting nitrile A is:
Options
- APropanenitrile
- BBenzonitrile
- CButanenitrile
- DEthanenitrile
Correct answer
A. Propanenitrile
Step-by-step solution
The final product is n-propylbenzene ( C ₆ H ₅- CH ₂- CH ₂- CH ₃ ). This is formed by the Clemmensen reduction of ketone P . Since the Grignard reagent used is phenylmagnesium bromide ( C ₆ H ₅ MgBr ), the phenyl group in the final product comes from the Grignard reagent. Therefore, the carbonyl carbon of ketone P must be the one attached to the phenyl ring. Thus, ketone P is propiophenone ( C ₆ H ₅- CO - CH ₂- CH ₃ ). Propiophenone is formed by the nucleophilic addition of phenylmagnesium bromide to a nitrile, fol