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Question 38

Given below are two statements:
Statement I:

under Clemmensen reduction conditions will give

Statement II:

under Wolff-Kishner reduction condition will give

In the light of the above statements, choose the correct answer from the options given below:

Statement I: True

  • Reactant: A keto-amide ($$\text{H}_2\text{N-C}(=\text{O})-\text{CH}_2-\text{CH}_2-\text{C}(=\text{O})-\text{CH}_3$$).
  • Reagent: Clemmensen reduction utilizes zinc amalgam in concentrated hydrochloric acid ($$\text{Zn(Hg)} / \text{HCl}$$).
  • Reaction:
    1. The strongly acidic medium ($$\text{HCl}$$) hydrolyzes the primary amide group ($$\text{-CONH}_2$$) into a carboxylic acid group ($$\text{-COOH}$$).
    2. The ketone group ($$\text{-C=O-}$$) is reduced to a methylene group ($$\text{-CH}_2-$$).
  • Product: Pentanoic acid ($$\text{HOOC-CH}_2-\text{CH}_2-\text{CH}_2-\text{CH}_3$$), which matches the product shown in Statement I.

Statement II: False

  • Reactant: A halo-ketone ($$\text{Cl-CH}_2-\text{CH}_2-\text{CO-CH}_3$$).
  • Reagent: Wolff-Kishner reduction uses hydrazine and a strong base ($$\text{NH}_2\text{NH}_2 / \text{KOH}$$) at high temperatures.
  • Reaction: While the carbonyl group is targeted for reduction to an alkane, the presence of a strong base ($$\text{KOH}$$) induces a highly favorable competing side reaction—dehydrohalogenation (elimination of $$\text{HCl}$$). Instead of obtaining the simple reduced haloalkane ($$\text{Cl-CH}_2-\text{CH}_2-\text{CH}_2-\text{CH}_3$$), elimination reactions dominate, making the statement false.
  • Statement I is true.
  • Statement II is false.

Correct Answer: [C] Statement I is true but Statement II is false

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