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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: kims on November 23, 2008, 08:23:30 PM

Title: base catalyzed amide hydrolysis?
Post by: kims on November 23, 2008, 08:23:30 PM

how is this possible? in a protein, for an aspartate, the side chain, can get hydrolyzed right. but how. is the hydroxyl group a strong enough nucleophile to attack the carbonyl carbon? I thought the nitrogen is donating electrons strongly, and its not like you can protonate the nitrogen in basic solution. What's going on?