Question:

Propose a detailed mechanism for the reaction of propanone with two mole equivalent of methanol.....

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in the presence of an acid catalyst. Also include resonance structures of both the substrate and the intermediate

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  1. I shall give you the basic idea. Why dont you try it out yourself? If you still dont get, you can then ask again.

    First step is nucleophilic attack by the alcohol on the carbonyl carbon to generate the hemiacetal, which in most cases is highly unstable.

    Then, in presence of the dry acid catalyst, the OH is protonated to form a carbocation. This will not rearrange (Think why). This is then readily attacked by another molecule of alcohol to give the final product - an acetal.

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