Organic Chemistry PDF

Organic Chemistry I

Course Highlights

This course features a full set of problem sets with solutions, along with lecture handouts and other materials used by students in the course.

Course Description

5.12 is an introduction to organic chemistry, focusing primarily on the basic principles to understand the structure and reactivity of organic molecules. Emphasis is on substitution and elimination reactions and chemistry of the carbonyl group. The course also provides an introduction to the chemistry of aromatic compounds.

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.

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

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