5.12 | Spring 2003 | Undergraduate

Organic Chemistry I

Lecture Handouts

This section contains notes used to supplement the lectures for the course. Some lecture notes apply to multiple class sessions. The Readings column refers to relevant sections in the course textbook, L. G. Wade, Jr. Organic Chemistry, 5th ed. The first half of the lectures were given by Dr. Sarah Tabacco, while the second half of the lectures were given by Prof. Barbara Imperiali.

First Half of the Semester

1 General Class Information. Review of Lewis Bonding Theory Sarah Tabacco (PDF) Ch. 1
2 Resonance Sarah Tabacco   Ch. 1
3 Review of Molecular Orbital Theory, Hybridization/LCAO Sarah Tabacco (PDF) Ch. 2
4 Acidity Sarah Tabacco (PDF) Ch. 1
5 Bond Lengths and Strengths/Alkanes Sarah Tabacco (PDF) Ch. 3
6 Conformational Analysis Sarah Tabacco   Ch. 3
7 Cycloalkanes Sarah Tabacco   Ch. 3
8 Cyclohexane Sarah Tabacco   Ch. 3
9 Stereochemistry Sarah Tabacco (PDF) Ch. 5
10 Stereochemistry Sarah Tabacco   Ch. 5
11 Free Radical Reactions: Thermo/Kinetics Sarah Tabacco (PDF) Ch. 4
12 Free Radical Reactions: Thermo/Kinetics Sarah Tabacco (PDF) Ch. 4
13 Alkyl Halides/SN2 Sarah Tabacco (PDF) Ch. 6
14 SN2/SN1 Sarah Tabacco   Ch. 6
15 SN1/E1 Sarah Tabacco   Ch. 6
16 E1/E2 Sarah Tabacco   Ch. 6
17 E2 Sarah Tabacco   Ch. 6
18 Structure and Synthesis of Alkenes Sarah Tabacco   Ch. 7

Second Half of the Semester

19-21 The Alkene Double Bond: A Focus of Reactivity.
Polar and Concerted Addition Reactions. Hydrogenation, Addition of HX (Markovnikov Addition), Halogenation. Epoxidation, Hydroboration (Anti-Markovnikov Addition), Osmylation and Ozonolysis. Alkene Polymerization.
Barbara Imperiali (PDF) 7.1, 7.2, 7.7, 8.1, 8.2, 8.3-8.5, 8.8, 8.10-8.11, 8.12-8.15, 8.16
22-24 ALKYNES: Structure and Bonding.
Introduction to the Alkyne Triple Bond.

ALKYNES: Synthesis and Reactions. Alkylation of Acetylide Anions (A Carbon Nucleophile). Addition Reactions to Alkynes, Hydrogenation, Halogenation and HX. Hydration of Alkynes, Tautomerization.

Barbara Imperiali (PDF) 9.1-9.5, 9.6, 9.7, 9.9
25-26 ALCOHOLS: Structure, Synthesis and Reactions. Structure and Bonding. Acidity (brief review)Synthesis of Alcohols (methods to date and new strategies). Organometallic Reagents, Reactivity and Basicity. Reaction of Carbonyl Compounds with Grignard and Organolithium Reagents. REDOX Relationships amongst Alcohols, Aldehydes and Ketones and Carboxylic acids. Alcohols as Nucleophiles (Formation of Alkoxides) and Electrophiles (Formation of Osylates). Esterification. Barbara Imperiali (PDF) 10.1-10.6, 10.7, 10.8, 10.9-10.12, 11.1-11.3, 11.5-11.9, 11.12, 11.14
27-28 AROMATIC COMPOUNDS: Structure and Reactions.
2, 3, and 4 Pi Electron Systems. Benzene - The Prototypic Aromatic System. What is “Aromaticity”? Huckel’s Rule. Identifying Aromatic Systems. Charged and Neutral Species. Polycyclics and Heterocyclic. Reaction Chemistry of Aromatic Compounds - Electrophilic Aromatic Substitution: Halogenation, Nitration, Sulfonylation and Friedel-Crafts Alkylation and Acylation.
Barbara Imperiali (PDF) 15.1-15.4, 16.1-16.10, 16.13, 17.1-17.5, 17.10-17.11
29-31 Directing Effects in Electophilic Aromatic Substitution. Nucleophilic Aromatic Substitution. Strategies in the Synthesis of Multisubstituted Benzene Derivatives.

CARBONYL COMPOUNDS: Summary of Various Types of Carbonyl Compounds - Aldehydes and Ketones, Carboxylic Acids and Carboxylic Acid Derivatives (Acid Chlorides, Acid Anhydrides, Esters and Amides).

Barbara Imperiali (PDF) 17.6-17.9, 17.12, 18.1-18.4
32 Synthesis of Aldehydes and Ketones Barbara Imperiali    
33 Reactions of Carbonyl Compounds with the Carbonyl Group as an Electrophile with H, C, N and O Nucleophiles. Barbara Imperiali    
34 Carbonyl Reactivity at the Alpha C-H (Enols and Enolates) Barbara Imperiali    
35 Wrap Up Barbara Imperiali    

Course Info

As Taught In
Spring 2003
Learning Resource Types
Problem Sets with Solutions
Lecture Notes