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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro129

Select the correct choices of method for converting the carbonyl group into in the substrate named.

  1. AClemmensen reduction (Zn-Hg, conc. ) of 4-methoxyacetophenone to 1-ethyl-4-methoxybenzene
  2. BClemmensen reduction of 4-tert-butoxyacetophenone with the tert-butyl ether kept intact
  3. CWolff-Kishner reduction (KOH, heat) of ethyl 4-oxopentanoate to ethyl pentanoate with the ester kept intact
  4. DWolff-Kishner reduction of 4-chloroacetophenone to 1-chloro-4-ethylbenzene

Answer: A, D

An aryl methyl ether survives hot conc. HCl, and an aryl chloride survives KOH/hydrazine, so (A) and (D) are suitable. The tert-butyl ether is cleaved by conc. HCl, so (B) fails. The ester is saponified by hot KOH, so (C) fails.
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