Note from Dr. Black -

Only certain of these excellent slide shows have been copied to our local host (and thus will load very quickly); the others are linked to the WWU site.  These will take longer to load, but the wait is worth it!  We should all be very grateful to Professor Pavia for making these slides publically available; it's clear that a fearsome amount of work went into their generation.

Obviously, the chapter numbers below do not correspond to McMurry, but the chapter titles and slide names should easily guide you to the set you want to see.

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• Downloading and Viewing Instructions

Some of these files are quite large (5-10 Mb) and may require some time to download.

• Chap 1 : Lewis Structures, Condensed Formulas, Alkanes

• Introductory Material
• Lewis Diagrams
• Evaluation of Lewis Diagrams
• Condensed, Line, Polygon Notation
• Alkanes - Constitutional Isomers
• Functional Groups, Classes

• Chap 2 : VSEPR Theory, Orbitals, Hybridization

• VSEPR Theory
• Hybridization I
• Hybridization II
Using your models
• Orbital Arrays and Antibonding Orbitals

• Chap 3 : Nomenclature, Alkanes Reactions, Conformational Isomers

• IUPAC Nomenclature
• Common Groups and Complex Group Nomenclature
• Reactions of Hydrocarbons
• Conformations - Ethane
• Conformations - Butane
• class demo problems

• Chap 4 : Cycloalkane Conformations; Alkenes, Double Bond Geometry

• Small Rings - C3,C4,C5
• Cyclohexane - Chair/Boat/Twist
• Substituted Cyclohexanes
• Rings : Cis and trans
• Steroids
• Terpenes
• Alkenes: cis/trans and E/Z
• Alkenes: Heats of Hydrogenation
• Bicyclic Compounds and Nomenclature

• Chap 5 : Stereochemistry

• Optical Activity and Polarimetry
• Chirality and Stereocenters
• Meso Isomers, Enantiomers and Diastereomers
• Fischer Projections
• Carbohydrates: Nomenclature and Structure
• Stereocenters Other than Carbon

• Chap 6 : Resonance

• Basic Concepts and Analogies
• Pushing Electrons / Anions and Cations
• Pushing Electrons / Neutral Systems / Benzene
• Pi Molecular Orbital Systems
• Two Problems

• Chap 7 : Acids and Bases

• Acid-Base Theory / pKa's of Acids
• pKa's of Bases

• How to Draw a Mechanism

• Chap 8 : Electrophilic Addition Reactions


• Additions I - Alkenes I
• Short Review
• Additions II - Alkenes II
• Additions III - Alkenes III
• Additions IV - Alkynes
• Additions V - Addition Polymers
• Hydrogenation- Review of Chaps 3,4 & 6

• Chap 9 : Elimination Reactions


• Eliminations I - E2
• Eliminations II - E2
• Eliminations III - E1
• Eliminations IV - E1
• Eliminations V - Hofmann, Syn Eliminations, Carbenes
• Eliminations to form Alkynes

• Chap 10 : Nucleophilic Substitution Reactions


• Nucleophilic Substitution I - Intro & Kinetics
• Nucleophilic Substitution II - Stereochemistry
• S_N2 Animation
• Nucleophilic Substitution III - Substrate Structure
• Nucleophilic Substitution IV - Nucleophilicity & Solvents
• Nucleophilic Substitution V - Elimination vs. Substitution
• Tosylates, Brosylates, etc.
• Nucleophilic Substitution VI - Neighboring Groups

• Chap 12 : Nucleophilic Substitution Reactions


• Conversion of Alcohols to Halides & Tosylates
• Ethers, Acetylides, Nitriles and Amines
• Synthesis from Nature

• Chap 11 : Infrared Spectroscopy


• Infrared Spectroscopy I : Basic Theory, Hydrogen Deficiency Index
• Infrared Spectroscopy II : CH , OH and NH
• Infrared Spectroscopy III : CN, CC Triple Bonds
• Infrared Spectroscopy IV : C=O Carbonyl Compounds
• Infrared Spectroscopy V : C=O and C=C Conjugation and Ring Size
• Infrared Spectroscopy VI : C-O Alcohols and Ethers
• Infrared Spectroscopy VII : C-X Halides and C-H oops + How to Use IR Spectra

• Chap 13 : Nuclear Magnetic Resonance Spectroscopy


• NMR Spectroscopy I : Basic Theory, Instrumentation
• NMR Spectroscopy II : Integration, Chemical Shift
• NMR Spectroscopy III : n+1 Rule, Coupling Constants
• NMR Spectroscopy IV : Survey of NMR Spectra
• NMR Spectroscopy V : Survey of NMR Spectra (cont )
• NMR Spectropscopy VI : Aromatics, OH and NH protons
• NMR Spectroscopy VII : Tree Diagrams
• NMR Spectroscopy VIII : Carbon-13 Spectra
• NMR+IR Spectroscopy : Combined Problems (Set 1)
• NMR+IR Spectroscopy : More Combined Problems (Set 2)
• Answers to Combined Problems can be found on the Sample Exams page.

• How to Draw a Mechanism
• Review of Catalytic Hydrogenation
• Review of Synthetic Reactions

• Chap 14 : Alkenes II - Oxidation and Reduction


• Epoxides, Glycols, Cleavage
• Ozonolysis
• Hydrogenation, Hydroboration, Oxymercuration
• Ring Formation: Cyclohexenes and Cyclopropanes
• Multistep Synthesis

• Chap 15 : Organometallic Compounds


• Alkyllithium Reagents, Synthesis of Acids and Alcohols
• Grignard Reagents, Synthesis of Acids and Alcohols
• Reactions of Epoxides, Alkynes, Lithium Dialkylcuprates
• Reaction of Nitriles, Esters, Organocadmium Reagents

• Review of Carbohydrates : Chap 5

• Chap 16 : Aldehydes and Ketones I


• Nucleophilic Addition to C=O
• Hydrates, Acetals, Hemiacetals, Carbohydrates
• Imines, Enamines, Hydrazones, Removal of C=O

• Chap 17 : Aldehydes and Ketones II


• Reduction of Aldehydes and Ketones
• Reduction of Esters and Acid Chlorides
• Oxidation of Alcohols; Synthesis

• Chap 18 : Carboxylic Acids


• Synthesis; Acid Strength

• Chap 19 : Carboxylic Acid Derivatives


• Nucleophilic Acyl Substitution:

Acid Chlorides, Anhydrides, Esters, Amides
• Hydrolysis Reactions, Enamines, Nitriles

Fats and Oils

• Chap 21 : Reactions of a-Hydrogens


• Alkylation and Halogenation Reactions
• Aldol and Claisen Condensations
• Conjugate (Michael) Additions, Robinson Annelation
• Synthesis of Ketones, Acyloin Condensation
• Enols and Enol Content

• Chap 22 : Aromatic Substitution Reactions


• Nomenclature, Electrophilic Aromatic Substitution
• Directivity, Aromaticity, Huckel Rule