2
$\begingroup$

My mechanism for this conversion is an intramolecular attack sn2 to displace Cl- anion. OH- can then attack this aziridinium intermediate, but will the nucleophile not attack preferentially at the most substituted site (where greatest positive charge resides i.e. tertiary center)? This gives the incorrect product?

enter image description here

$\endgroup$

1 Answer 1

2
$\begingroup$

Steric factors are more important here. The positive charge resides on the N and the nucleophile attacks the least hindered site hence the product is as drawn.

$\endgroup$

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.