What is the mechanism for the acid-catalyzed esterification of formic acid and 2-butanol?
1 Answer
Dec 22, 2016
Here is a likely mechanism. It's worth noting that you may have an elimination side product. Can you imagine how step 4 might branch off to form the side product?
(The intermediate there is a poor nucleophile by virtue of its bulk, but has two electron-donating groups that facilitate Lewis basic behavior. Surprisingly, that branched step also leads to formation of the major product!)
- I assume you know how to write a proton transfer mechanistic step, from protonated 2-butanol to formic acid's carbonyl oxygen (which has the highest electron density on formic acid). If you don't, it is demonstrated in reverse on step 6.
- The 2-butanol can nucleophilically attack the carbonyl carbon, since it's been activated by the acid catalysis and is more electrophilic.
- Proton transfer pt 1.
- Proton transfer pt 2.
- Tetrahedral collapse. Either hydroxyl group could have been protonated; I just chose the one that makes the mechanism look more like the one you see in my textbook (Bruice).
- Deprotonation of the carbonyl oxygen to yield the product.
It is hydronium that exists at the end of the mechanism, rather than protonated 2-butanol, because a protonated alcohol generally has a lower