Question

What does tautromerization mean?

Answer 1

Tautomers are constitutional isomers that interconvert readily. The interconversion process represents tautomerization.

Explanation:

The best example of tautomerization is the keto-enol tautomerization; certainly this process is exploited by organic chemists to form `C-C` bonds.

`RC(=O)CH_2R'rightleftharpoonsRC(-OH)=CHR'`

Here a `C-H` bond has been broken, and both `C=C` and `O-H` bonds have been formed (under most circumstances this equilibrium lies strongly to the left). Because the enolic proton is reasonably acidic it can be deprotonated to give the enolate, `RC(-O^-)=CHR'`, which is a resonance isomer of the carbanion, `RC(=O)-C^(-)HR'`.