The major product formed in the following reaction is: i. I₂, pyridine iii. NaBH₄, CeCl₃· 7H₂O · ABC26OR0384
Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · Exam: CSIR NET DEC 2018 · Marks: 2 · Difficulty: Medium
The major product formed in the following reaction is: 
i. $\mathrm{I_2}$, pyridine 
iii. $\mathrm{NaBH_4}$, $\mathrm{CeCl_3\cdot 7H_2O}$
i. $\mathrm{I_2}$, pyridine iii. $\mathrm{NaBH_4}$, $\mathrm{CeCl_3\cdot 7H_2O}$(a)
(b)
(c)
(d)
Answer
Answer: C ✓ checked by 4AB · confidence high
The source book printed A; on checking, C is correct — see the explanation.
Explanation
I₂/pyridine α-iodinates the enone; Stille coupling with vinyltributyltin installs the vinyl group at C-2; Luche reduction (NaBH₄/CeCl₃) reduces the ketone 1,2 to the allylic alcohol 2-vinylcyclohex-2-en-1-ol (c).
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