Why does LiAl4/NH4Cl on an amide not produce a secondary alcohol?

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

csx

Membership Revoked
Removed
10+ Year Member
Joined
May 8, 2013
Messages
1,074
Reaction score
204
rather is just gets completely reduced....why?

Members don't see this ad.
 
Usually, if you use LiAlH4 to reduce any carboxylic acid derivative, you will get its respective alcohol. However, one exception is for amides because when you try to reduce the amide using LAH, the NH2 is a horrible leaving group, and it can't leave. Thus, the OH leaves instead and you form an amine.
 
  • Like
Reactions: 1 user
Top