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A Levels Chemistry (9701)•9701/11/O/N/20
Question 24 from 9701/11/O/N/20

Explanation

Nucleophilic substitution with cyanide to extend carbon chain

Steps:

  • Butanoic acid (C3H7CO2H) requires adding one carbon to the propyl chain from 1-iodopropane (C3H7I).
  • Primary alkyl iodides undergo SN2 substitution with nucleophiles to replace I.
  • CN- from ethanolic KCN acts as nucleophile, forming propanenitrile (C3H7CN).
  • Hydrolysis of the nitrile in the second stage yields butanoic acid.

Why C is correct:

  • Ethanolic KCN delivers CN- for SN2 reaction, converting C3H7I to C3H7CN per the general formula R-X + KCN → R-CN + KI.

Why the others are wrong:

  • A: Aqueous NaOH substitutes to form propan-1-ol (C3H7OH), not extending the chain.
  • B: Ethanolic ammonia substitutes to form propan-1-amine (C3H7NH2), yielding an amine.
  • D: Ethanolic NaOH favors elimination to propene or substitution to propan-1-ol, not chain extension.

Final answer: C

Topic: Organic synthesis

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