A Levels Chemistry (9701)•9701/12/O/N/23

Explanation
Secondary alcohol oxidizes to ketone under given conditions
Steps:
- X (C4H10O) is oxidized to Y (C4H8O) with excess acidified K2Cr2O7 under reflux, indicating loss of 2H without forming carboxylic acid (which would be C4H8O2).
- Y forms orange crystals with 2,4-DNPH, confirming Y is an aldehyde or ketone (carbonyl group).
- Y produces H2 with Na metal, but given formula and conditions, this likely distinguishes from acid (standard test: ketones do not, acids do); thus Y is ketone.
- Only secondary alcohols yield ketones (C4H8O) under these conditions; primary yield acids, tertiary do not react.
Why A is correct:
- A is butan-2-ol (secondary alcohol), oxidizes to butan-2-one (C4H8O ketone), matching Y's formula and tests.
Why the others are wrong:
- B (butan-1-ol, primary) oxidizes to butanoic acid (C4H8O2), not C4H8O.
- C (2-methylpropan-2-ol, tertiary) does not oxidize, remains C4H10O.
- D (2-methylpropan-1-ol, primary) oxidizes to 2-methylpropanoic acid (C4H8O2), not C4H8O.
Final answer: A
Topic: Hydroxy compounds
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