What does tautromerization mean?

1 Answer
Aug 27, 2016

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'.