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In the following carbocation, $H/CH_3$ that 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 $

1 Answer

In the carbocation, H- shift occurs from $c-2$ to $c-3$ because :
(i) the positive charge developed on $c-2$ is m conjugation with the -OH group.
(ii) also the $CH_3$ group at $c-2$ shows + I effect and stabilized the positive charge.
So, $H\;at\;C-2 $
Hence d is the correct answer.
answered Feb 24, 2014 by meena.p

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