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A Levels Chemistry (9701)•9701/11/M/J/22
Question 26 from 9701/11/M/J/22

Explanation

Reaction types in alcohol to nitrile conversion

Steps:

  • First step (X): CH3CH2OH to CH3CH2Br replaces OH with Br using reagent like HBr or PBr3; Br⁻ acts as nucleophile attacking the carbon, displacing H2O.
  • Second step (Y): CH3CH2Br to CH3CH2CN replaces Br with CN using KCN; CN⁻ acts as nucleophile attacking the carbon, displacing Br⁻.
  • Both are SN2 mechanisms typical for primary alkyl compounds.
  • Eliminate options with free-radical (alkane halogenation) or electrophilic substitution (aromatic rings).

Why B is correct:

  • Option B matches both steps as nucleophilic substitution, where a nucleophile bonds to an electrophilic carbon, displacing a leaving group (per SN2 definition).

Why the others are wrong:

  • A: Free-radical substitution applies to alkanes like chlorination of methane, not alcohol conversion; electrophilic substitution is for benzene derivatives.
  • C: Second step is nucleophilic (CN⁻ attacks), not electrophilic substitution.
  • D: Identical to C, so second step incorrectly labeled electrophilic.

Final answer: B

Topic: Organic synthesis

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