Skip to content
doubtly
Topic: Aldehydes and ketones: HCN, NH3 derivatives, Grignard, oxidation, reduction (Wolff-Kishner, Clemmensen)· Organic Compounds Containing Oxygen

Identify product (A) in the following reaction :3-(3-acetylphenyl)-substituted cyclohexyl methyl ketone: a cyclohexane ring bearing an acetyl group, joined to a benzene ring bearing an acetyl group (meta), [conc. HCl]Zn-Hg (A) + 2H_2O

Identify product (A) in the following reaction :

3-(3-acetylphenyl)-substituted cyclohexyl methyl ketone: a cyclohexane ring bearing an acetyl group, joined to a benzene ring bearing an acetyl group (meta), \(\xrightarrow[\text{conc. HCl}]{\text{Zn-Hg}}\) (A) + 2H\(_2\)O

reactant structure, reagent and four structure options

1. both acetyl groups reduced to methyl groups, CH\(_3\) (structure)

2. both acetyl groups reduced to ethyl groups (structure)

3. both acetyl groups reduced to CH(OH)CH\(_3\) (structure)

4. both acetyl groups reduced to CH\(_2\)OH, i.e. HOCH\(_2\)- (structure)

1 answer

Best answer

Answer: 2. both acetyl groups reduced to ethyl groups (structure)

Key idea: Zn-Hg/conc. HCl is the Clemmensen reduction, which converts \(\mathrm{>C=O}\) into \(\mathrm{>CH_2}\).

Each acetyl group \(\mathrm{-COCH_3}\) becomes \(\mathrm{-CH_2CH_3}\) (ethyl); the loss of the two oxygens appears as 2 \(\mathrm{H_2O}\). The rings are unaffected. The product has two ethyl groups: option 2. Option 1 would need loss of a carbon; options 3 and 4 are alcohols, which Clemmensen does not give.

Doubtly AI · 30 Oct 2026 AI-generated · not yet verified Report
Was this answer helpful?

Your answer

Log in or create a free account to answer this question.