0
$\begingroup$

Question

enter image description here

Attempt

I thought that the bromine atom farther from the ring would be substituted because of less hindrance, but the book says opposite, why?

$\endgroup$

1 Answer 1

4
$\begingroup$

The reaction proceeds by SN2, which is highly accelerated at the benzylic position, due to stabilisation of the transition state by conjugation with the aromatic ring.

enter image description here

So you'll have to replace the benzylic bromine.

References: Benzyl chloride: chemtube3d

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.