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Hydrolysing amides

There are two ways of doing this. The first one is protonating the C=O to make it more electrophillic.


The second is brute force by OH-:


Both methods require vigorous conditions - high acid/base concentration, high heat, and long reaction times. Secondary and tertiary amides hydrolyse even more slowly.

A secret weapon to force the hydrolysis of a tertiary amide is to use a very strong base such as Potassium tert-butoxide. This deprotonates the tetrahedral intermediate:


It may be difficult to make an amine anion leave, but something has to, and O2- or a carbanion are much harder to push off.

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