Most reactions that can be done under acidic conditions can also be done under b

Question

Most reactions that can be done under acidic conditions can also be done under basic conditions – for example, conversion of a ketone into a ketal.

That said, the reason Fischer esterifications require acid catalysis is that protonating the acid makes the electrophile (the carbonyl carbon) a better electrophile.

We could presumably make the nucleophile (an alcohol) a better nucleophile, which is usually done through deprotonation.

Explain why reacting an alkoxide with a carboxylic acid will not result in a Fischer esterification. What happens instead and why?

Explanation / Answer

Alkoxide is better base than a better nucleophile, it will first seek or react with a proton rather than

act as a nucleophile so it will not lead to esterification .

The reacftion that occurs is the acid base reaction,

RO-   +   R-COOH -------->    RO-H    + R-COO-

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