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Question:

Which of the following on heating with aqueous KOH produces acetaldehyde?

CH3COCl

CH2ClCH2Cl

CH3CHCl2

CH3CH2Cl

Solution:

The reaction of CH3CH2Cl with aqueous KOH involves nucleophilic substitution. However, this reaction does not produce acetaldehyde.

CH3CHCl2 on reaction with aqueous KOH undergoes hydrolysis. The reaction proceeds through a carbocation intermediate that undergoes rearrangement to produce acetaldehyde.

CH3CHCl2 + KOH → CH3CH(OH)Cl → CH3CHO + HCl

Therefore, CH3CHCl2 produces acetaldehyde on heating with aqueous KOH.

Hence, option C is correct.