Question:

Arrange the following in increasing order of their reactivity towards HCN: Di-tert-butyl ketone, Acetaldehyde, Acetone.

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Addition of HCN to a carbonyl is a nucleophilic addition.
Updated On: Jun 16, 2026
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Solution and Explanation

Concept: Addition of HCN to a carbonyl is a nucleophilic addition. Reactivity falls when (a) more alkyl groups push electron density onto the carbonyl carbon (lowering its positive charge) and (b) bulky groups block the approach of the nucleophile (steric hindrance). Aldehydes are more reactive than ketones.
Answer: Increasing order of reactivity towards HCN is: Di-tert-butyl ketone < Acetone < Acetaldehyde. Reason: di-tert-butyl ketone has two very bulky tert-butyl groups that both crowd the carbonyl carbon and push in electron density, so it is least reactive. Acetone (a ketone with two small methyl groups) is more reactive. Acetaldehyde, being an aldehyde with only one methyl group and a hydrogen, has the least crowding and the most positive carbonyl carbon, so it is most reactive.
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