Neucleophilic Acyl substitution of unsymmetrical Acid Anhydrides

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The discussion centers on the reaction between an acid anhydride and an alcohol, resulting in the formation of an ester and a carboxylic acid. The initial example involves a symmetrical acid anhydride, leading to a straightforward outcome. However, the focus shifts to unsymmetrical acid anhydrides, represented as R1COO-COR2. The key question is which alkyl group, R1 or R2, will be incorporated into the ester and which will form the carboxylic acid. It is noted that the alcohol attacks the more reactive carbonyl carbon, influenced by the presence of electron-withdrawing groups and steric factors. For instance, if R is a methyl group (CH3) and R' is an ethyl group (CH3CH2), the ester formation is favored from the carbonyl carbon associated with the less sterically hindered alkyl group, leading to a preference for the methyl carbonyl in this scenario.
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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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sodaboy7 said:
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 ?
Alcohol attack to more reactive carbonyl carbon which produced ester, reactivity of carbonyl carbon towards electron withdrawing group attached or less steric alkyl group. If R= CH3 and R'= CH3CH2 , ester formation preferred R carbonyl...
 
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