Ester enolates - PowerPoint PPT Presentation

Keto-enol tautomerization

Keto-enol tautomerization. enolization “normal” aldehydes and ketones K eq = ~ 10 -8. Stabilized aldehydes and ketones.  -diketones K eq = ~ 10. Mechanism for acid-catalyzed enolization. Mechanism for acid-catalyzed enolization. Reactions of enols:  -halogenation. An example.

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21.8 Barbiturates

21.8 Barbiturates. O. COCH 2 CH 3. H 2 N. H 2 C. C. O. COCH 2 CH 3. H 2 N. O. Barbituric acid is made from diethyl malonate and urea. +. O. COCH 2 CH 3. H 2 N. H 2 C. C. O. COCH 2 CH 3. H 2 N. O. O. H. N. C. C. O. H 2 C. N. C. O. H.

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21.9 Michael Additions of Stabilized Anions

21.9 Michael Additions of Stabilized Anions. O. O. C. C. ••. H 3 C. C. OCH 2 CH 3. –. H. O. O. C. C. ••. C. OCH 2 CH 3. CH 3 CH 2 O. –. H. Stabilized Anions. The anions derived by deprotonation of  -keto esters and diethyl malonate are weak bases.

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