Organic Chemistry by Brown, Iverson, Anslyn, Foote | Mayya's Study Guide | Chapter 19

Chapter 19: Enolate Anions and Enamines

Table of Contents:

1. Formation and Reactions of Enolate Anions: An Overview

2. Aldol Reaction

3. Claisen and Dieckmann Condensations

4. Enamines

5. Acetoacetic Ester Synthesis

6. Malonic Ester Synthesis

7. Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

8. Crossed Enolate Reactions Using LDA

9. Mayya'sTricks For Chapter 19

Enols and Enolate Ions

Keto-Enol Tautomers In Acid And Base

Aldol Reaction

Aldol reaction is one of the most important reactions in this chapter and in semester 2 of organic chemistry. This reaction can occur under basic or acidic conditions.

Under Basic conditions

Mechanism for Base Catalyzed Aldol Condensation

Under Acidic conditions

Mechanism for Acid Catalyzed Aldol Condensation

Mayya's Trick: How to predict the product of Aldol Condensation

1. Draw two molecules of the starting material and align =O of one with alpha carbon of the other

2. Get rid of =O and connect the carbon that had =O with the alpha carbon on another molecule through a double bond

Trick: How to predict the product of Aldol Condensation

There is also Crossed and Intramolecular Aldol Reactions. Crossed aldol is when instead of attacking itself, the enol or enolate attack another molecule of ketone or aldehyde. Intramolecular aldol is when one end of the molecule attacks another end of the molecule, forming a ring.

Mayya's Trick on how to predict reactants if the product of aldol condensation is given

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