Question

Quest In the following carbocation,$\frac{H}{C{H}_3}$ that is most likely to migrate to the positive charged carbon is:

$\stackrel{1}{H_{3}C}-\underset{OH}{\underset{|}{\stackrel{H}{\stackrel{|}{C^2}}}}-\underset{H}{\underset{|}{\stackrel{3^{+}}{C}}}-\underset{C{H}_3}{\underset{|}{\stackrel{H}{\stackrel{|}{C^4}}}}-C{H}_3$

• A.
• B.
• C.
• D.

Answer 1

The correct option is D

Due to mesomeric effect (+) of -OH group the electron density on benzene ring increases.

Therefore, an electrophile can easily attack there

In the given carbocation, $H^{+}$ migrates from $c_2$ to $c_3$.

as (I) changes to (II) $\leftrightarrow H_{3}C-\underset{OH}{\underset{+||}{C}}\underset{\left(II\right)}{\underset{H}{\underset{|}{\stackrel{H}{\stackrel{|}{C}}}}}\underset{C{H}_3}{\underset{|}{\stackrel{H}{\stackrel{|}{C}}}}C{H}_3$

It is no longer a carbocation (more stable).