Section 1: Reviewing General Chemistry

Section 2: Acids and Bases

Instructor's Notes for Section 2

Bronsted-Lowry, Lewis Acids/Bases

Equilibrium, pKa

What makes one acid more acidic than another

Five factors that affect strength of conjugate base, 1) Electronegativity

Practice Homework for Section 2

Practice Homework for Section 2 (Key)

Quiz for Section 2

Quiz for Section 2 (Key)

Section 3: Alkanes and Cycloalkanes

Instructor's Notes for Section 3

Classification of Hydrocarbons, Alkanes

Naming Alkanes, Complex Groups

Examples of Alkanes

Cycloalkanes

Functional groups, Alkyl Halides, Ethers

Alcohols, Amines

Physical properties, Intramolecular Forces, Melting point, Boiling point, Solubility

Conformations of Acyclic Alkanes and Cyclohexanes

Conformations of Open Chain Compounds - Ethane

Conformations Analysis of Butane

Cycloalkanes: cyclopropane, cyclobutane, cyclopentane, cyclohexane

Chair conformation of cyclohexane, Monosubstituted cyclohexane

Disubstituted cyclohexane, cis and trans isomerism)

Practice Homework for Section 3

Practice Homework for Section 3 (Key)

Quiz for Section 3

Quiz for Section 3 (Key)

Section 4: Isomers

Instructor's Notes for Section 4

Isomers, Structural (or Constitutional) Isomers, Constitutional vs Conformational Isomers

Stereoisomers

E or Z configuration

Chirality

R and S configuration

Optical Activity

Diasteromers

Multiple Chirality Centers

Fisher Projections Pt1

Fisher Projections Pt2

Quiz for Section 4

Practice Homework Section 4

Practice Homework for Section 4 (Key)

Quiz for Section 4

Quiz for Section 4 (Key)

Section 5: Alkenes

Instructor's Notes for Section 5

Degree of Unsaturation or Index of Hydrogen Deficiency (IHD)

Calculating DU

From DU – Drawing Structures from Molecular Formula

Naming Alkenes

Naming Alkenes – Examples

Classification of Alkenes, cis- and trans-

Classification of Alkenes, E or Z

Reaction Coordinate Diagrams, Exergonic vs Endergonic Reactions

Reaction Coordinate Diagram for the Addition of HBr to 2-Butene

Practice Homework for Section 5

Practice Homework for Section 5 (Key)

Quiz for Section 5

Quiz for Section 5 (Key)

Section 6: Reactions of Alkenes

Instructor's Notes for Section 6

Hydrohalogenation

Hydrohalogenation: regiochemistry, stereochemistry and Markovnikov’s Rule

Double Slap Mechanisms, Oxymercuration–demercuration of Alkenes Part 1

Oxymercuration–demercuration of Alkenes Part 2

Oxymercuration–demercuration of Alkenes Part 3

Halogenation Part 1

Halogenation Part 2

Halogenation Part 1

Halohydrin Formation Part 1

Halohydrin Formation Part 2

Epoxidation

Dihydroxylation with osmium tetraoxide

Permanganante

Ozonolysis Part 1

Ozonolysis Part 2

Catalytic Hydrogenation

Carbenes Part

Practice Homework for Section 6

Practice Homework for Section 6 (Key)

Quiz for Section 6

Quiz for Section 6 (Key)

Section 7: Reactions of Alkynes

Instructor's Notes for Section 7

Naming Alkynes Part 1

Naming Alkynes Part 2

Naming Alkynes Part 3

Hydrohalogenation Part 1

Hydrohalogenation Part 2

Addition of Water to an Alkyne

Hydroboration, Catalytic Hydrogenation, Alkylation

Practice Homework for Section 7

Practice Homework for Section 7 (Key)

Quiz for Section 7

Quiz for Section 7 (Key)

Section 8: Delocalized Electrons

Instructor's Notes for Section 8

Facts about Benzene

Alkene vs Benzene Reactivity, Resonance Energy

Molecular Orbital for cyclic molecules

Aromatic, Nonaromatic and Antiaromatic Terminology

More MO Energy Diagrams Part 1

More MO Energy Diagrams Part 2

More MO Energy Diagrams Part 3

Huckle’s Rule

Examples

Heterocyclic Aromatic Compounds

More Heterocyclic Examples

Polycyclic Aromatic Hydrocarbons, Annulenes, Aromatic and Antiaromatic Ions

Annulenes

Aromatic and Antiaromatic Ions

Diels- Alder Reaction

Stereochemistry of the Diels Alder Reaction – Part 1

Stereochemistry of the Diels Alder Reaction – Part 2

Stereochemistry of the Diels Alder Reaction – Part 3

Stereochemistry of the Diels Alder Reaction – Part 4

Polymers

Practice Homework for Section 8

Practice Homework for Section 8 (Key)

Quiz for Section 8

Quiz for Section 8 (Key)

Section 9a: Substitution Reactions of Alkyl Halides

Instructor's Notes for Section 9a

The SN2 Reaction

SN2 Reactions

Fisher Projections and SN2 Reactions

Mechanism for the SN2 Reaction

Nature of the Leaving Group

Reactivity of the Nucleophile Part 1

Reactivity of the Nucleophile Part 2

Reactivity of the Nucleophile Part 3

Reactivity of the Nucleophile Part 4

Reactivity of the Nucleophile Part 5

Solvent Effects

Structure of the Electrophile

Summary of SN2 Reaction

The SN1 Reaction

SN1 Reactions

SN1 Mechanism Part 1

SN1 Mechanism Part 2, Optical Activity, Solvolysis Reactions, Polar Protic Solvents and SN1 Reactions

SN1 Rates: Effect of Substituents

Summary of SN1 Reaction

Examples of SN2 and SN1 Reactions Part 1

Examples of SN2 and SN1 Reactions Part 2

Intramolecular Reactions

Competing Reactions Part 1

Competing Reactions Part 2

Section 9b: Elimination Reactions of Alkyl Halides

Instructor's Notes for Section 9b

Antiperiplanar Attack, Labeling Carbons and Hydrogens

Zaitsev’s Rule, Hofmann’s Rule

The Antiperiplanar Proton – A True Love Story

Elimination Unimolecular Reactions - E1 and E1 Mechanism

Regiochemistry and selectivity of E1 products (Zaitsev’s Rule)

Potential Energy Reaction Coordinate for E1 Products vs SN1

Dehydration of alcohols: the E1 reaction becomes dominant

Dehydration of alcohols - Mechanism

Practice Problems

Dehydration of Alcohols and Carbocation Rearrangements

Comparison of the SN2 and SN1, E2 and E1 Reactions

Practice Homework for Section 9a & 9b

Practice Homework for Section 9a & 9b (Key)

Quiz for Section 9a & 9b

Quiz for Section 9a & 9b (Key)

Section 10: Alcohols, Epoxides and Ethers

Instructor's Notes for Section 10

Synthesis of Alcohols, Preparation of Alkyl Halide (R-X) from Alcohols

Using LiAlH4 and NaBH4 as Nucleophiles to make Alkanes

Nucleophilic Ring Opening of Epoxides (Oxiranes) to Produce Alcohols

Ring Opening of Epoxides Cont.

Ring Opening of Oxiranes Review, Epoxides Examples

Oxidation Reactions, Oxidizing Agents

Ethers

Williamson Ether Synthesis: Preparation of Alkoxide RO-

Multi-Step Reactions – Examples of Williamson Ether Synthesis, Ethers via SN1,

Phosphorous Oxychloride – a dehydrating agent for alcohols

Practice Homework for Section 10

Practice Homework for Section 10 (Key)

Quiz for Section 10

Quiz for Section 10 (Quiz)

Section 11: Organometallic Compounds

Instructor's Notes for Section 11

Grignard Reaction, Reactivity of organometallic reagents

Nucleophilic Addition of Organometallics (Normal 1,2-Addition), 3o Alcohol, via Grignard Reaction (Normal 1,2-Addition)

Carboxylic Acids, via Grignard Reaction with CO2

Conjugate 1,4-Additions, Normal/Conjugate Examples, Synthesis

The Suzuki Reaction, Examples of the Suzuki Reaction

The Heck Reaction, Examples of Heck Reactions

Practice Homework for Section 11

Practice Homework for Section 11 (Key)

Quiz for Section 11

Quiz for Section 11 (Key)

Section 12: Radicals

Instructor's Notes for Section 12

Radicals, Radical Stability

Radical Generation, Radical Generation via Heat

Mechanism for Monochlorination, Mechanism for Monobromination

Practice Problems

Halogenation Converts an Alkane into a Useful Compound

Addition of HBr in the Presence of Peroxide, Mechanism for the Addition of HBr in the Presence of Peroxide

N-Bromosuccinimide (NBS) is Used to Brominate Allylic Carbons, N-Bromosuccinimide (NBS) Mechanism

Designing a Synthesis 1, 2, and 3

Practice Homework for Section 12

Practice Homework for Section 12 (Key)

Quiz for Section 12

Quiz for Section 12 (Key)

Practice Homework for Section 9a & 9b

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OCHEM I

Practice Homework for Section 9a & 9b