© 2000 Prentice Hall. All rights reserved.

Dr. Glaser's Visualization Center
To accompany Bruice, Organic Chemistry, 3/e, Chapter 19

Theme Molecule Name Chemical Formula
Keto-Enol Tautomerism keto form of acetone (S) H3C-CO-CH3
Keto-Enol Tautomerism enol form of acetone (S) H2C=C(OH)-CH3
Keto-Enol Tautomerism keto form of acetylacetone (S) H3C-CO-CH2-CO-CH3
Keto-Enol Tautomerism enol form of acetylacetone (S) H3C-C(OH)=CH-CO-CH3
Enolate Ions and Their Formation enolate of acetone (S) H2C=C(O-)-CH3
Enolate Ions and Their Formation lithium diisopropylamide (LDA) (S) LiN[CH(CH3)2]2
Halogenations of Carbonyl Compounds alpha-chloro acetaldehyde (S) Cl-H2C-C(O)-H
Halogenations of Carbonyl Compounds alpha-chloro acetic acid (S) Cl-H2C-C(O)-OH
Kolbe Schmitt Carboxylation aspirin (S) C9H8O4
Aldol Reaction beta-hydroxy aldehyde (S) H3C-CH(OH)-CH2-CHO
Claisen Condensation beta-keto ester (S) H3C-C(O)-CH2-CO-OCH3
Enzymes (from PDB) aldolase (S) enzyme

[a] Unless otherwise noted, structures were optimized at the correlated ab initio level MP2(full)/6-31G*.
[b] The structures of the enolate anions were optimized at the correlated ab initio level MP2(full)/6-31+G*.
[c] The structure of aspirin was optimized at the ab initio level RHF/6-31G*.
[d] Structures marked pdb were obtained from the protein data bank.