Claisen - 12-2-2011 at 06:18
In Hofmann degradation reaction of amides, the base employed (OH-) abstracts a proton from the -NH2 group where as in the base catalysed hydrolysis of
amides, the amide undergoes a nucleophilic attack by the base.
What actually governs the reaction of OH-?
madscientist - 12-2-2011 at 12:27
With amides, deprotonation doesn't yield a reaction, hence it's unimportant. With the Hofmann rearrangement, deprotonation is part of the reaction
pathway. Also, the bromine on the nitrogen helps stabilize the anion, making deprotonation more favorable.
Claisen - 12-2-2011 at 12:40
I did not understand your first sentence.
The reaction initiates only after the deprotonation i.e. it is the first step, why is it unimportant?
madscientist - 12-2-2011 at 13:35
Crap - I meant to say "With hydrolysis of amides..." Sorry! 
Claisen - 12-2-2011 at 15:11
Thanks for your help!!