0
$\begingroup$

Why does $\ce{-NH_2}$ shows more +M effect that $\ce{-NHR}$ and $\ce{-NR_2}$? My first conclusion was totally opposite of the reality. I thought, as the alkyl groups are attached to the Nitrogen the lone lone pair on nitrogen should be easily available. But it doesn't seem to be happening. What is the actual cause?

$\endgroup$
2
$\begingroup$

It is because the bulky alkyl groups provide repulsion to the lone pair such that their orientations change. Due to the change in orientation the %s character changes and the lone pair becomes less available. This is not the case with hydrogen.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

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