Chapter 22 Additions and Condensations of Enolate Ions

Alpha Substitution

Condensation Reactions

Base-Catalyzed Keto-Enol Tautomerism

Acid-Catalyzed Keto-Enol Tautomerism

Racemization

Energy Diagram of Enolate Reaction with an Electrophile

Alpha Halogenation of Ketones

Mechanism of Haloform Formation

Bromoform Reaction

Iodoform Reaction with a Secondary Alcohol

Mechanism of Acid-Catalyzed a-Halogenation

Hell-Volhard-Zelinsky Reaction

Hell-Volhard-Zelinski Reaction: Step 1

Hell-Volhard-Zelinski Reaction: Step 2

Alkylation of Enolate Ions

Mechanism of Enolate Formation

Alkylation of an Enamine

Acylation of Enamines

Aldol Condensation

Mechanism of Base-Catalyzed Aldol Condensation

Aldol Condensation of Acetone

Chapter 23 Carbohydrates and

Nucleic Acids

Structures of Glucose and Fructose

Classicfication of Monosaccharides

D and L Series of Sugars

Degradation of an Aldose

The D Family of Aldoses

Erytho and Threo Diastereomers

Dissymetric Molecules

Epimers

Mechanism of Cyclic Hemiacetal Formation

Glucose Conformations

Fructose

Anomers of Glucose

Anomers of Fructose

Mutarotation

Base-Catalyzed Epimerization of Glucose

Base-Catalyzed Enediol Rearrangement

Oxiation of Aldoses Using Bromine Water

Nitric Acid Oxidation

Tollens Test

Nonreducing Sugars

Aglycones

Ether Formation

Ester Formation

Osazone Formation

Ruff Degradation

Kiliani-Fischer Synthesis

Periodic Acid Cleavage of Carbohydrates

Disaccharides

b-Glucosidic Linkage

a Glucosidic Linkage

Linkage of Two Anomeric Carbons: Sucrose

Cellulose

Amylose

Amylose Helix

Amylopectin

RNA Polymer

Cytidine, Uridine, Adenosine, and Guanosine

Common Ribonucleotides

Phosphate Linkages

Common Deoxyribonucleosides

Base Pairing in DNA and RNA

Strands of DNA

Double Helix

Replication