Q14 · CSIR NET Chemistry, June 2012
Paper: CSIR NET June 2012 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · Marks: 2 · Difficulty: Medium
The major product formed in the following reaction is: 
1. DIBAL (1 eq.) 2. $\mathrm{CH_2{=}CHMgBr}$ 3. PCC
1. DIBAL (1 eq.) 2. $\mathrm{CH_2{=}CHMgBr}$ 3. PCC(a)
(b)
(c)
(d)
Answer
Answer: A ✓ checked by 4AB · confidence high
Explanation
DIBAL reduces the lactone to the lactol; vinyl Grignard adds to the masked aldehyde, opening it to a diol; PCC oxidises the ring alcohol to the cyclohexanone and the allylic alcohol to the vinyl ketone (a).
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