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

The product formed in the following chemical reaction is :2-(methyl-substituted) cyclohexanone bearing CH_2-C(=O)-OCH_3 and CH_3 groups [C_2H_5OH]NaBH_4 ?

The product formed in the following chemical reaction is :

2-(methyl-substituted) cyclohexanone bearing \(CH_2-C(=O)-OCH_3\) and \(CH_3\) groups \(\xrightarrow[C_2H_5OH]{NaBH_4}\) ?

keto-ester cyclohexanone reacting with NaBH4/C2H5OH and four product structures

1. Cyclohexane ring with OH, \(CH_3\) and \(CH_2-CH(OH)-OCH_3\) substituents

2. Cyclohexanone ring with \(CH_3\) and \(CH_2-CH_2-OH\) substituents

3. Cyclohexane ring with OH, \(CH_3\) and \(CH_2-CH(OH)-CH_3\) substituents

4. Cyclohexane ring with OH, \(CH_3\) and \(CH_2-C(=O)-OCH_3\) substituents

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Answer: 4. Cyclohexane ring with OH, \(CH_3\) and \(CH_2-C(=O)-OCH_3\) substituents

Key idea: \(\mathrm{NaBH_4}\) is a mild reducing agent. It reduces aldehydes and ketones but does not reduce esters.

The ketone C=O of the ring is reduced to a secondary alcohol (OH), while the ester group \(\mathrm{-CH_2COOCH_3}\) stays unchanged. So the product is the ring bearing OH, \(\mathrm{CH_3}\) and \(\mathrm{CH_2COOCH_3}\).

The other options show the ester reduced or altered, which \(\mathrm{NaBH_4}\) cannot do.

Doubtly AI · 30 Oct 2026 AI-generated · not yet verified Report
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