Q12 · CSIR-NET Chemistry, June 2013
Paper: CSIR-NET June 2013 · Subject: Organic Chemistry · Chapter: Natural Products · Topic: Natural Products – General · Marks: 2 · Difficulty: Hard
$\alpha$-Pinene on reaction with dilute alkaline $\mathrm{KMnO_4}$ produces a diol, which on further oxidation with chromium trioxide gives product A, which undergoes a positive haloform test. The compound A is
(a)
(b)
(c)
(d)
Answer
Answer: C ✓ checked by 4AB · confidence high
Explanation
Dilute KMnO₄ hydroxylates the α-pinene double bond to pinanediol; CrO₃ cleaves the diol to the keto acid pinonic acid (c), whose acetyl group gives a positive iodoform test.
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