A Levels Chemistry (9701)•9701/13/O/N/21

Explanation
Vicinal diol identification via iodoform and oxidative cleavage Steps:
- Yellow precipitate with alkaline iodine indicates positive iodoform test, requiring CH3CH(OH)- group in the alcohol.
- Substance Z gives red-brown precipitate with Fehling's solution, confirming Z is an aldehyde.
- Oxidation yields a mixture including Z, indicating oxidative cleavage of a 1,2-diol to carbonyl compounds, one being an aldehyde.
- Only option A, CH3CH(OH)CH2OH (propane-1,2-diol), is a vicinal diol with the required CH3CH(OH)- structure.
Why A is correct:
- CH3CH(OH)CH2OH undergoes iodoform reaction due to CH3CH(OH)- and cleaves oxidatively to CH3CHO and HCHO, both aldehydes (Z reduces Fehling's).
Why the others are wrong:
- B: CH3CH(OH)CH2CH2OH is a 1,3-diol (non-vicinal); no cleavage, oxidation yields ketone primarily, not aldehyde mixture.
- C: CH3CH(OH)CH2CH3 is secondary alcohol only; oxidizes to butanone (ketone), no aldehyde.
- D: CH3OCH2CH2CH3 is an ether; lacks OH group, fails both tests.
Final answer: A
Topic: Hydroxy compounds
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