Complete Segment Index | Organic Chemistry Reference Lectures | Haverford College

Complete Segment Index

Lecture 1 — Introduction

1.01 Foreword
1.02 Methane
1.03 Saturated Hydrocarbons
1.04 Structure — Isomers

Lecture 2 — Conformation

2.01 Ethane
2.02 Propane
2.03 n-Butane
2.04 n-Pentane

Lecture 3 — Constitution

3.01 Review
3.02 Butane and Isobutane
3.03 C5H12 Hydrocarbons
3.04 C6H14 Hydrocarbons
3.05 C7H16 Hydrocarbons

Lecture 4 — Configuration

4.01 Enantiomerism
4.02 Introduction to CIP
4.03 CIP Mechanics
4.04 Diastereoisomerism — 3,4-Dimethylheptane
4.05 Achiral Diastereoisomers — 3,4-Dimethylhexane
4.06 A More Complicated Case — 3,4,5-Trimethylheptane

Lecture 5 — Hydrocarbon Rings

5.01 Introduction to Rings
5.02 Strain Energy
5.03 Dimethyl Cyclopropanes
5.04 Dimethyl Cyclobutanes
5.05 Cyclohexane Chair Conformation
5.06 Dimethyl Cyclohexanes

Lecture 6 — Stereotopism

6.01 Constitutionally Distinguishable Groups
6.02 Homotopic Groups
6.03 Enantiotopic Groups
6.04 Diastereotopic Groups
6.05 Stereotopism in 3,5-Dimethylheptane
6.06 Re and Si Faces and Spaces
6.07 Stereotopism in Ethanol

Lecture 7 — Carbon Bonding

7.01 Hydrogen Molecule
7.02 Csp3 Bonding — Methane
7.03 Csp2 Bonding — Ethylene
7.04 Csp2 Bonding — Ethylene, Continued
7.05 Csp Bonding — Acetylene
7.06 Allene (1,2-Propadiene)
7.07 Tau Bonds ("Bent Bonds")
7.08 E/Z Nomenclature

Lecture 8 — Bonding in Carbon Polyene Systems

8.01 1,3-Butadiene
8.02 1,3,5-Hexatriene
8.03 The Special Case of Benzene
8.04 The Generalized Concept of Aromaticity
8.05 Hexatriene-Cyclohexadiene Interconversion
8.06 Butadiene-Cyclobutene Interconversion

Lecture 9 — Basic Ideas of Thermodynamics and Kinetics

9.01 Simple Application of Gibbs' Equation
9.02 Simple Application of Eyring's Equation
9.03 Thermodynamic vs. Kinetic Control of a Reaction

Lecture 10 — Functionality

10.01 The Concepts Primary, Secondary, Tertiary

Lecture 11 — Acidity and Basicity

11.01 Aqueous Acids and Bases — pKA
11.02 The Lewis Nucleophile-Electrophile Definition
11.03 Avoiding Error When Invoking Aqueous Acids and Bases
11.04 Potential Delocalization of an Anion Affects Acidity
11.05 Kinetic vs. Thermodynamic (Equilibrium) Acidity
11.06 Nucleophilicity vs. Basicity

Lecture 12 — Oxidation and Reduction — Forms of Writing Reactions

12.01 Balancing Redox Reactions
12.02 Reduction of Alkenes — Forms of Writing Reactions
12.03 Oxidation of Alkenes to Oxiranes (Epoxides)
12.04 Oxidation of Alkenes to 1,2-Diols (Cis-Oxidation)
12.05 Diastereoselectivity in Redox Reactions
12.06 Enantioselectivity in Redox Reactions

Lecture 13 — Bimolecular Nucleophilic Substitution and Elimination Reactions

13.01 Bimolecular Nucleophilic Substitution
13.02 The SN2 Mechanism
13.03 The Special Case of Primary Halide Synthesis
13.04 Steric Effects on the SN2 Mechanism
13.05 The E2 Mechanism Competes with SN2
13.06 Stereochemistry of the E2 Reaction
13.07 Synthesis of Isopropyl Methyl Ether

Lecture 14 — Unimolecular Nucleophilic Substitution and Elimination Reactions

14.01 The SN1 Mechanism
14.02 Carbocations
14.03 Synthesis of tert-Butyl Methyl Ether
14.04 The E1 Mechanism
14.05 Summary of Nucleophilic Substitution Reactions

Lecture 15 — Electrophilic Addition to Alkenes

15.01 Addition of HX to Alkenes
15.02 Acid Catalyzed Polymerization of Alkenes
15.03 Epoxidation of cis-2-Butene
15.04 Epoxidation of trans-2-Butene
15.05 Bromination of Alkenes
15.06 Stereochemistry of Bromine Elimination vs. Addition
15.07 Electrophilic Aromatic Substitution

Lecture 16 — Introduction to the Carbonyl Group

16.01 Introduction to Carbonyl Bonding and Reactivity
16.02 Introduction to Carbonyl Nomenclature
16.03 Reaction of the Carbonyl Group with Electrophiles and with Nucleophiles
16.04 Nucleophilic Addition to the Carbonyl Group vs. Nucleophilic Substitution at Carbonyl

Lecture 17 — Alcohol Synthesis via Nucleophilic Addition to the Carbonyl Group

17.01 Oxidation Reactions of Alcohols to Carbonyl Derivatives
17.02 Reduction of Aldehydes and Ketones to Alcohols with LiAlH4 and NaBH4
17.03 Grignard Reagents — Nucleophiles for Carbonyl Addition
17.04 A General Synthesis of Alcohols
17.05 Synthesis of 3-Hexanol
17.06 Synthesis of 3-Methyl-3-Hexanol
17.07 Diastereoselective Alcohol Syntheses and the Possibility of Enantioselective Alcohol Syntheses

Lecture 18 — Further Nucleophilic Addition Reactions to the Carbonyl Group

18.01 Hydrates
18.02 Acetals and Ketals
18.03 Imines, Oximes, Hydrazones
18.04 Addition of Cyanide Anion to the Carbonyl and Imine Functionalities — a-Hydroxy- and a-Amino-Acids

Lecture 19 — Nucleophilic Substitution at the Carbonyl Group

19.01 Carboxylic Acids — Formation and Activation
19.02 Esters — Formation
19.03 Esters — Hydrolysis and Transesterification
19.04 Reactions of Esters with Grignard and Hydride Reagents
19.05 Amides — Formation
19.06 Amides — Hydrolysis
19.07 Nitriles and Their Hydrolysis to Amides and Carboxylic Acids — Tautomers

Lecture 20 — Consequences of Hydrogen Acidity at Carbonyl a-Carbon — Aldol and Related Reactions

20.01 Enolate and Enol
20.02 Tau Bond Interpretation of Enolate Formation
20.03 Aldol Condensation
20.04 Aldol Condensation, Continued
20.05 Claisen (Ester) Condensation — Dieckmann Condensation
20.06 Alkylation and Decarboxylation of b-Ketoesters
20.07 Uses of the Claisen
20.08 Michael Reaction
20.09 Robinson Annulation

Lecture 21 — Brief Introduction to Carbohydrates

21.01 Glucaric Acid is Chiral
21.02 Ruff Degradation — Arabaric Acid is Chiral
21.03 Kiliani Synthesis — Glucose and Mannose are C-2 Epimers
21.04 Mannaric Acid is Chiral — Osazones
21.05 Emil Fischer's Solution to the Glucose Problem
21.06 Glucose Exists Predominantly in a Glucopyranose Ring
21.07 Proof of Structure of 2,3,4,6-Tetramethylglucose
21.08 How to Transform the Glucopyranose Structure into its Proper and Conventional Chair Conformational Rendering
21.09 Furanose Rings
21.10 Disaccharides — Lactose
21.11 Polysaccharides — Cellulose and Starch

Lecture 22 — Important General Subjects for Review

22.01 The Concept of Retrosynthetic Analysis
22.02 Writing Mechanisms in Organic Chemistry — The Notational Device of "Curved-Arrow Pushing"
22.03 A Concluding Word