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Question
Write the mechanism (using curved arrow notation) of the following reaction :

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Solution

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Write the mechanism of the following reaction :

Write the mechanism of the following reaction :

When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place:
\[\begin{array}{cc}
\phantom{...................................}\ce{Br}\\
\phantom{..................................}|\\
\ce{CH3 - CH - CH - CH3 ->[HBr] CH3 - C - CH2 - CH3}\\
|\phantom{.........}|\phantom{...................................}|\phantom{...........}\\
\ce{CH3}\phantom{...}\ce{OH}\phantom{...............................}\ce{CH3}\phantom{.......}\\
\end{array}\]
Give a mechanism for this reaction.
(Hint: The secondary carbocation formed in step II rearranges to a more
stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.)
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