(E)-3-bromo-3-hexene when treated with CH₃O⁻ in CH₃OH gives · ABC26OR0627

Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Exam: GATE 2000-2022 · Marks: 2 · Difficulty: Easy

(E)-3-bromo-3-hexene when treated with $\mathrm{CH}_{3}\mathrm{O}^{-}$ in $\mathrm{CH}_{3}\mathrm{OH}$ gives
(a)3-hexyne
(b)2-hexyne
(c)2, 3-hexadiene
(d)2, 4-hexadiene
Answer
Answer: C ✓ checked by 4AB · confidence medium
Explanation
In (E)-3-bromo-3-hexene the vinylic H on C-4 is cis to Br, so anti E2 to the alkyne is impossible; methoxide instead removes the allylic C-2 H, giving the allene 2,3-hexadiene (c).

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