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A Levels Chemistry (9701)•9701/13/O/N/21
Question 26 from 9701/13/O/N/21

Explanation

Cyanohydrin Formation Mechanism Steps:

  • Acetone (CH3COCH3) is a ketone that undergoes nucleophilic addition with HCN.
  • CN⁻ attacks the electrophilic carbonyl carbon, forming a tetrahedral alkoxide intermediate.
  • The alkoxide abstracts a proton from HCN, yielding the cyanohydrin CH3C(OH)(CN)CH3 and regenerating CN⁻.
  • This shows CN⁻ acts catalytically, as it is regenerated and not net consumed.

Why D is correct:

  • Cyanide ion (CN⁻) catalyzes the reaction by serving as the nucleophile in addition and being regenerated via proton transfer from HCN, per the standard base-catalyzed mechanism.

Why the others are wrong:

  • A: The product CH3C(OH)(CN)CH3 has two identical CH3 groups attached to the central carbon, so no chiral center.
  • B: The reaction is nucleophilic addition (CN⁻ attacks carbonyl), not electrophilic.
  • C: While the intermediate contains -CN, the statement's wording implies the product forms an intermediate with -CN, which is unclear and not accurate.

Final answer: D

Topic: Carbonyl compounds

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