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Unformatted text preview: intermediate, which (c) eliminates to reform the carbonyl moiety. Basic catalyzed esterification of carboxylic alcohols using alcohols does not work due to acid-base chemistry, i.e. deprotonation of the carboxylic acid. The conversion of esters to carboxylic acids is known as ester hydrolysis. Under acidic conditions, the mechanism is simply the reverse of the Fischer esterification. Ester hydrolysis can also be conducted using aqueous base. The mechanism for basic hydrolysis or saponification was discussed in class. It is another example of an acyl substitution. Accordingly, the mechanism involves the same 3 fundamental steps described above. Using methanol, compare and contrast the mechanisms for acid catalyzed ketal formation and acid catalyzed esterification....
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- Spring '08