An acid anhydride can be formed under equilibrium conditions by reacting an ester with a carboxylic acid, as shown below. Reasonable yield is achieved if the equilibrium can be shifted by exploiting Le Châtelier's principle. -R" HO + + R ОН R' `OR" R `R' (a) Provide a complete, detailed mechanism for this reaction. (b) In general, the above equilibrium favors the reactants. However, if the ester that is used is the one shown here, then the equilibrium favors the products. Explain why. R' O.

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An acid anhydride can be formed under equilibrium conditions by reacting an ester with a carboxylic acid, as shown
below. Reasonable yield is achieved if the equilibrium can be shifted by exploiting Le Châtelier's principle.
-R"
HO
+
+
R
ОН
R'
`OR"
R
`R'
(a) Provide a complete, detailed mechanism for this
reaction.
(b) In general, the above equilibrium favors the
reactants. However, if the ester that is used is
the one shown here, then the equilibrium favors
the products. Explain why.
R'
O.
Transcribed Image Text:An acid anhydride can be formed under equilibrium conditions by reacting an ester with a carboxylic acid, as shown below. Reasonable yield is achieved if the equilibrium can be shifted by exploiting Le Châtelier's principle. -R" HO + + R ОН R' `OR" R `R' (a) Provide a complete, detailed mechanism for this reaction. (b) In general, the above equilibrium favors the reactants. However, if the ester that is used is the one shown here, then the equilibrium favors the products. Explain why. R' O.
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