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A Levels Chemistry (9701)•9701/11/O/N/18
Question 40 from 9701/11/O/N/18

Explanation

Cyanohydrin Formation via Nucleophilic Addition

Steps:

  • Recognize the reaction as cyanohydrin synthesis, where HCN (with KCN as catalyst) adds to a carbonyl group, treating ethanol as context for ethanal (acetaldehyde) analog.
  • CN⁻ nucleophile attacks the electrophilic carbonyl carbon, breaking the C=O π bond.
  • The carbon of CN bonds to the carbonyl carbon, forming a new C–C σ bond.
  • Protonation of the alkoxide yields the cyanohydrin, with no breakage of C–H or C–N bonds.

Why B is correct:

  • In cyanohydrin formation, the product structure RCH(OH)CN includes a new C–C bond between the original carbonyl carbon and the CN carbon, per nucleophilic addition mechanism.

Why the others are wrong:

  • A: The C–H bond in HCN remains intact; H⁺ adds to oxygen without breaking substrate C–H.
  • C: The C≡N triple bond in cyanide persists unbroken throughout the addition.
  • D: Option incomplete; no bonding change specified.

Final answer: B

Topic: Carbonyl compounds

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