What does tautromerization mean?

1 Answer
anor277
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'#.

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