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NEET CHEMISTRYMedium

Reaction of a carbonyl compound with one of the following reagents involves nucleophilic addition followed by the elimination of water. The reagent is:

A

a Grignard reagent

B

hydrazine in presence of feebly acidic solution

C

hydrocyanic acid

D

sodium hydrogen sulphite

Step-by-Step Solution

The reaction of aldehydes and ketones with ammonia derivatives (H2NZH_2N-Z) is a characteristic nucleophilic addition-elimination reaction.

  1. Mechanism: The nitrogen atom of the nucleophile attacks the carbonyl carbon (nucleophilic addition) to form a tetrahedral intermediate. This intermediate then loses a molecule of water (elimination) to form a compound with a >C=NZ>C=N-Z double bond.
  2. Hydrazine: Hydrazine (NH2NH2NH_2NH_2) reacts with carbonyl compounds in a feebly acidic medium to eliminate water and form hydrazones. >C=O+H2NNH2H+>C=NNH2+H2O>C=O + H_2N-NH_2 \xrightarrow{H^+} >C=N-NH_2 + H_2O
  3. Other Options:
  • Grignard reagent: Undergoes nucleophilic addition to form an alkoxide, which yields an alcohol upon hydrolysis (no water elimination in the addition step).
  • Hydrocyanic acid (HCN): Undergoes nucleophilic addition to form cyanohydrins (no water elimination).
  • Sodium hydrogen sulphite: Undergoes nucleophilic addition to form bisulphite addition products (no water elimination).
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