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A Levels Chemistry (9701)•9701/12/M/J/19
Question 24 from 9701/12/M/J/19

Explanation

Primary alcohol from carboxylic acid reduction yielding single dehydration product

Steps:

  • LiAlH4 reduces carboxylic acids (RCOOH) to primary alcohols (RCH2OH), so W is primary: options A or C.
  • Dehydration of primary alcohols with conc. H2SO4 follows Zaitsev's rule, forming alkenes via E1 mechanism with possible carbocation rearrangements.
  • Butan-1-ol (A) forms a secondary carbocation, yielding but-1-ene and but-2-ene (multiple products).
  • Propan-1-ol (C) has no rearrangement possible, yielding only propene (CH3CH=CH2).

Why C is correct:

  • Propan-1-ol is the primary alcohol from propanoic acid reduction that dehydrates to a single alkene (propene) due to only one beta-hydrogen position and no stable alternative carbocation.

Why the others are wrong:

  • A: Dehydration gives mixture of but-1-ene and but-2-ene via rearrangement.
  • B: Secondary alcohol, not from carboxylic acid reduction; dehydration gives but-1-ene and but-2-ene.
  • D: Secondary alcohol, not from carboxylic acid reduction; though dehydration gives only propene, it violates the reduction condition.

Final answer: C

Topic: Hydroxy compounds

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