What are "tautomers"tautomers?

1 Answer
anor277
Mar 5, 2016

Tautomers are special cases of constitutional isomers that readily interconvert by (typically) the formal migration of an hydrogen atom or a proton

Explanation:

The classic case of tautomerism is given by hydrogen transfer between ketones and enols:

R(O=)C-CH_2R' rightleftharpoons R(HO)C=CHR'

As written, the equilibrium lies strongly to the left. Certain circumstances can drive the equilibrium to the right, as is the case of C-C bond formation with diethyl malonate.

Lactams, amides, and amines can undergo related proton transfer to give other examples of tautomerism.

If you wanted to label a ketone with deuterium, ""^2H, how could use the reaction above to effect the labelling given quantites of D_2O?

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