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NEET CHEMISTRYHard

The major product H of the given reaction sequence is: CH3CH2COCH3HCNG95%H2SO4,ΔHCH_3-CH_2-CO-CH_3 \xrightarrow{HCN} G \xrightarrow{95\% H_2SO_4, \Delta} H

A

CH3-CH=C(CH3)-COOH

B

CH3-CH=C(CH3)-CN

C

CH3-CH(OH)-C(CH3)(OH)-COOH

D

CH3-CH=C(CH3)-CONH2

Step-by-Step Solution

The reaction proceeds in two main stages:

  1. Cyanohydrin Formation: The reaction of Butanone (CH3CH2COCH3CH_3-CH_2-CO-CH_3) with HCN is a nucleophilic addition reaction. The cyanide ion (CNCN^-) attacks the carbonyl carbon, forming a cyanohydrin intermediate (G): 2-hydroxy-2-methylbutanenitrile. G:CH3CH2C(OH)(CH3)CNG: CH_3-CH_2-C(OH)(CH_3)-CN
  2. Hydrolysis and Dehydration: Heating with concentrated (95%) H2SO4H_2SO_4 performs two functions:
  • Hydrolysis: The nitrile group (CN-CN) is hydrolysed to a carboxylic acid group (COOH-COOH).
  • Dehydration: The acid acts as a dehydrating agent, removing a water molecule (the OH-OH group and a hydrogen from an adjacent carbon). According to Zaitsev's rule, the major product is the more substituted alkene. Thus, hydrogen is removed from the CH2CH_2 group (C3) rather than the CH3CH_3 group, forming a double bond between C2 and C3.

The final product H is 2-Methylbut-2-enoic acid (CH3CH=C(CH3)COOHCH_3-CH=C(CH_3)-COOH).

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