A. What is an Organic Molecule?

1.1-1.8

Lewis Structures (review)

1.17

Structural Formulas

1.9-1.15

Molecular Geometry: Quantum Mechanical Model (review)

2.1-2.2

Hydrocarbons ("the skeleton")

2.3-2.4

Polar and Non-Polar Compounds

2.5-2.12

Functional Groups ("the organs")

2.13-2.15

Physical Properties and Intermolecular Forces

B. Organic Reactions: General Principles

3.1

Organic Reaction Mechanisms

3.2-3.15

Acid-Base Reactions

C. Stereochemistry I: Conformational Analysis

4.1-4.2, 4.7-4.9

Conformational Analysis of Alkanes

4.10-4.15

Conformational Analysis of Cycloalkanes

D. Stereochemistry II: Chirality

5.1

Isomerism

5.2-5.6

Chirality and Enantiomers

5.7, 7.2

Nomenclature:R/S and E/Z systems

5.8-5.9

Optical Activity

5.11-5.14

More Than One Stereocenter: Enantiomers and Diastereomers

5.15-5.18

More about chirality.Separation of Enantiomers

E. How to Make Organic Molecules? Nucleophilic Substitution and Elimination Reactions

6.1-6.4

Nucleophilic Substitution Reactions

6.5-6.8

The Mechanism of SN2 Reactions

6.9-6.12

The Mechanism of SN1 Reactions

6.13

SN1 vs. SN2

6.14,7.10-7.12

Functional Group Transformations via Substitution

E. How to Make Organic Molecules? Nucleophilic Substitution and Elimination Reactions (continued)

6.15-6.17

Elimination Reactions: E1 & E2

6.18-6.19

Substitution vs. Elimination

7.3-7.8

Making Alkenes via Elimination Reactions

7.9

Making Alkynes via Elimination Reactions

11.14

SN1 and SN2 reactions with epoxides

F. Addition to Alkenes and Alkynes; Alcohols and Ethers

7.13-7.14

Addition to Alkenes: Hydrogenation

8.1-8.6

Addition to Alkenes: Markovnikov's Rule

8.7-8.11

Hydroboration-Oxidation: Anti-Markovnikov syn Hydration

8.12-8.14, 8.18-8.19

Electrophilic addition of halogens to alkenes and alkynes

8.16-8.18, 8.20, 11.13

Oxidation of Alkenes and Alkynes, Alkene epoxidation

11.4-11.12

Alcohols and Ethers: Reactivity and Synthesis