In the following carbocation, $\mathrm{H} / \mathrm{CH}_{3}$ that is most likely to migrate to the positively charged carbon is

JEE Advanced · 2009 · 12 Apr 2009 · Paper 2 · General Organic Chemistry

In the following carbocation,

H / CH_{3}

that is most likely to migrate to the positively charged carbon is

(A) $CH_{3}$ at C-4
(B)H at $C - 4$
(C) $CH_{3}$ at C-2
(D)H at $C - 2$ ✓ Correct

Answer: (D)

Solution

In carbocation rearrangements, migration occurs to form the most stable carbocation. The H at C-2 is most likely to migrate because this migration leads to a more stable tertiary carbocation with the positive charge on a carbon bearing an OH group, which can stabilize the charge through resonance.

JEE Advanced · 2009 · 12 Apr 2009 · Paper 2 · Single correct option

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