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NEET CHEMISTRYAldehydes, Ketones and Carboxylic AcidsHard

Question

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).

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Aldehydes, Ketones and Carboxylic Acids. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAldehydes, Ketones and Carboxylic Acidsproductreactionsequencechchcochxrightarrowhcn

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