5.12 | Spring 2003 | Undergraduate

Organic Chemistry I


1   Lecture 1
Review of Lewis Bonding (PDF)
Lecture 2 
2 Lecture 3
Molecular Orbital Theory, Hybridization (PDF) Problem Set #1 Due
Lecture 4
**Acidity (PDF)
Lecture 5 
Bond Lengths and Strengths/Alkanes (PDF)
3 Lecture 6
Conformational Analysis 
Review Session Problem Set #2 Due
Lecture 7
Exam 1 (during class period)
4 Lecture 8
Lecture 9 
Lecture 10
Stereochemistry (PDF)
5 Lecture 11 
Free Radical Reactions, Thermodynamics and Kinetics Problem Set #3 Due

Lecture 12 
Free Radical Reactions, 
Thermodynamics and Kinetics (PDF)
Lecture 13 
Alkyl Halides/SN2 (PDF)
6 Lecture 14 
Substitution Reactions of Alkyl Halides SN2/SN1 Problem Set #4 Due

Lecture 15
Substitution and Elimination Reactions of Alkyl Halides SN1/E1
Exam 2 (during class period)
7 Lecture 16 
Elimination Reactions of Alkyl Halides E1/E2 (PDF)
Lecture 17 
Elimination Reactions of Alkyl Halides E2
Lecture 18 
Structure and Synthesis of Alkenes
8 Lecture 19 
The Alkene Double Bond: A Focus of Reactivity. Polar and Concerted Addition Reactions. (PDF) Problem Set #5 Due

9   Lecture 20 
Hydrogenation, Addition of HX (Markovnikov Addition), Halogenation.
Lecture 21
Epoxidation, Hydroboration (Anti-Markovnikov Addition), Osmylation and Ozonolysis Alkene Polymerization. Problem Set #6 Due

10 Lecture 22 
ALKYNES: Structure and Bonding. Introduction to the Alkyne Triple Bond. (PDF)
Lecture 23
Alkylation of Acetylide Anions (A Carbon Nucleophile)
Lecture 24 
Addition Reactions to Alkynes, Hydrogenation, Halogenation and HX. Hydration of alkynes. Tautomerization. Problem Set #7 Due

11 Exam 3 (during class period) Lecture 25 
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. (PDF)
Lecture 26 
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 Tosylates). Esterification.
12   Lecture 27 
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. (PDF)
Lecture 28 
Reaction Chemistry of Aromatic Compounds – Electrophilic Aromatic Substitution: Halogenation, Nitration, Sulfonylation and Friedel-Crafts Alkylation and Acylation. Problem Set #8 Due

13 Lecture 29 
Directing Effects in Electophilic Aromatic Substitution (PDF)
Lecture 30 
Nucleophilic Aromatic Substitution. Strategies in the Synthesis of Multisubstituted Benzene Derivatives.
14     Lecture 31 
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). Problem Set #9 Due

15 Exam 4 (during class period) Lecture 32 
Synthesis of Aldehydes and Ketones
Lecture 33 
Reactions of Carbonyl Compounds with the Carbonyl Group as an Electrophile with H, C, N and O Nucleophiles.
16 Lecture 34 
Carbonyl Reactivity at the Alpha C-H (Enols and Enolates)
Lecture 35 
17 Final Exam (Duration 3 Hours)    

Course Info

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