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

Explanation
Carbonyl X is a symmetrical ketone that forms an achiral cyanohydrin and fails Fehling's test.
Steps:
- Carbonyl compounds react with HCN/NaCN to form cyanohydrins; aldehydes and ketones both do this.
- Fehling's reagent tests positive only for aldehydes (oxidizable to carboxylic acids), not ketones.
- X does not react with Fehling's, so X is a ketone (eliminate A and C, both aldehydes).
- Among ketones, propanone (D) forms an achiral cyanohydrin (CH3-C(OH)(CN)-CH3, identical substituents on central carbon), unlike butanone (B, chiral cyanohydrin with CH3 and CH2CH3 groups).
Why D is correct:
- Propanone is a symmetrical ketone (CH3COCH3); its cyanohydrin has a plane of symmetry, making it achiral, and ketones do not reduce Fehling's reagent.
Why the others are wrong:
- A. Butanal is an aldehyde; reacts with Fehling's.
- B. Butanone is an unsymmetrical ketone; forms chiral cyanohydrin.
- C. Propanal is an aldehyde; reacts with Fehling's.
Final answer: D
Topic: Carbonyl compounds
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