When alcohol reacts with symmetrical acid anhydride to form ester. We have the following reaction,
enter image description here
But if the acid anhydride used is unsymmetrical how can we identify the major product? For example in the following reaction which is ester is the major product? enter image description here I tried searching the internet for the mechanism of this reaction but was able to find none. Any help would be appreciated.

  • 1
    $\begingroup$ My feeling is that it will be determined by which R group confers more hindrance to the carbonyl group. If there isn't much difference then you will get close to a 1:1 mixture $\endgroup$
    – Waylander
    Sep 8 at 12:53
  • $\begingroup$ @Waylander Do you know which bond of the alcohol will break, C-O or O-H? Is it similar to the reaction of alcohols with carboxylic acid? $\endgroup$
    – Asher2211
    Sep 8 at 13:06
  • 1
    $\begingroup$ O-H will break. It is similar to the reaction of an alcohol with an acyl chloride or activated ester. The other product is the carboxylic acid $\endgroup$
    – Waylander
    Sep 8 at 13:33

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.