Neucleophilic Acyl substitution of unsymmetrical Acid Anhydrides


by sodaboy7
Tags: acid, acyl, anhydrides, neucleophilic, substitution, unsymmetrical
sodaboy7
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#1
Oct19-11, 10:40 PM
P: 81
Consider the following reaction:

RCOO-COR + R'-OH → RCOO-R' + RCOOH (where -R is an alkyl group)

In above reaction the acid anhydride and an alcohol forms ester and carboxylic acid.
The acid anhydride used in this case is a symmetrical on that is containing only one alkyl group (R). My question is that if it is unsymmetrical (say R1COO-COR2), which alkyl group will form ester and which alkyl group will form carboxylic acid. That is will ester formed will have R1 or R2 ?
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