Amide

[chiddler]

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What are ways to remove the amine group from an amide?

Does SOCl2 work? Or is that only with carboxylic acids? Acid?

 

[SaintJude]

Kaplan mentions only hydrolysis.
Reagents : Strong acid (e.g. H2SO4) or strong base (e.g. NaOH) / heat. Amides are the most stable carboxylic acid derivatives and that's why they require such extreme conditions.

You know this, but the acidic conditions will protonate the oxygen, so the carbonyl becomes more susceptible to nucleophilic attack. The product of this rx is a carboxylic acid and ammonia.

More info on rx:
http://www.mhhe.com/physsci/chemistry/carey5e/Ch20/ch20-3-4-1.html

 

[chiddler]

very cool, thanks very much. two questions wrong because didn't know about acid :'(