CHEM 260

UBC

Course Overview

Lessons & Practice

I. Welcome

1. Course Introduction & Bonding

1.4hr

1.1.1. Lewis Structures and Formal Charges9 min

1.1.2. How to Draw Lewis Structures5 min

1.1.3. Example: Lewis Structures5 min

1.1.4. Example: Lewis Structures5 min

1.1.5. Practice: Lewis Structures2 min

1.1.6. Practice: Lewis Structures5 min

1.2.1. Bonding Models

1.2.2. Practice: Valence Bond Theory/Hybridization3 min

1.3.1. Valence Bond Theory and Hybridization7 min

1.3.2. Example: Valence Bond Theory/Hybridization5 min

1.4.1. Molecular Orbital Theory4 min

1.5.1. VSEPR Theory5 min

1.5.2. Example: VSEPR2 min

1.5.3. Example: VSEPR3 min

1.5.4. Practice: VSEPR4 min

1.6.1. Polar Bonds6 min

1.6.2. Example: Polar Bonds3 min

1.6.3. Example: Polar Bonds 2 min

1.6.4. Practice: Polar Bonds 50 sec

1.7.1. Intermolecular Forces4 min

1.7.2. Melting and Boiling Point Comparison4 min

1.7.3. Example: Intermolecular Forces3 min

1.7.4. Example: Intermolecular Forces2 min

1.7.5. Practice: Intermolecular Forces1 min

1.8.1. Summary Sheet: The Basics

2. Resonance & Stereochemistry

1.5hr

2.1.1. Bonding in Delocalized Systems3 min

2.1.2. Example: Resonance Structures6 min

2.2.1. Summary Sheet: Isomers Flowchart

2.3.1. Constitutional Isomers5 min

2.3.2. Example: Constitutional Isomers4 min

2.3.3. Example: Constitutional Isomers3 min

2.4.1. Conformational Isomers6 min

2.4.2. Example: Conformational Isomers3 min

2.5.1. Geometric or Cis/Trans Isomers6 min

2.5.2. Example: Geometric Isomers4 min

2.5.3. Practice: Geometric Isomers 2 min

2.6.1. Chiral Molecules5 min

2.6.2. Cahn-Ingold-Prelog Rules4 min

2.6.3. Assigning R and S Nomenclature4 min

2.6.4. Example: Stereochemistry7 min

2.6.5. Example: Stereochemistry 24 min

2.6.6. Practice: Stereochemistry 2 min

2.6.7. Practice: Stereochemistry1 min

2.7.1. Optical Isomers13 min

2.7.2. Example: Optical Isomers3 min

2.7.3. Example: Optical Isomers 23 min

2.7.4. Practice: Optical Isomers 1 min

2.8.1. Summary Sheet: Stereochemistry

2.8.2. Summary Sheet: Determining Maximum Number of Stereoisomers

2.8.3. Summary Sheet: Nomenclature and Conformations of Alkanes and Cycloalkanes

3. Acids & Bases

56min

3.1.1. Acid/Base Equilibrium Fundamentals - Use of Acids and Bases in Organic Chemistry4 min

3.1.2. Key Definitions in Acids/Bases5 min

3.1.3. Acid/Base Equilibrium Constants2 min

3.1.4. Example: Acid/Base Arrows 3 min

3.2.1. Factors Influencing Acid/Base Strength2 min

3.2.2. Electronegativity1 min

3.2.3. Atom Size2 min

3.2.4. Resonance3 min

3.2.5. Hybridization3 min

3.2.6. Induction3 min

3.2.7. Aromaticity3 min

3.2.8. Example: Acid/Base Strength 3 min

3.2.9. Example: Acid/Base Strength 3 min

3.2.10. Practice: Acid/Base Equilibria 2 min

3.2.11. Practice: Acid/Base Equilibria 2 min

3.3.1. Important pKas You Should Know4 min

3.3.2. Relationship Between pH and pKa2 min

3.3.3. Amino Acids at Different pHs3 min

3.3.4. Practice: Amino Acids in Solution3 min

3.3.5. Practice: Amino Acids in Solution3 min

3.3.6. Summary Sheet: Amino Acids in Solution of Various pH

3.3.7. Summary Sheet: pKa's of Common Molecules

3.4.1. Summary Sheet: Chemical Equilibria and Acid/Base Chemistry

4. Radical Reactions

30min

4.1.1. Radical Stability4 min

4.1.2. Example: Radical Stability3 min

4.1.3. Example: Radical Stability1 min

4.1.4. Practice: Radical Stability1 min

4.2.1. Radical Reactions: Radical Halogenation7 min

4.2.2. Radical Reactions: Hydrohalogenation with a Peroxide7 min

4.2.3. Practice: Radical Reactions2 min

4.2.4. Practice: Radical Reactions2 min

4.2.5. Practice: Radical Reactions3 min

4.3.1. Summary Sheet: Radical Reactions

5. Reactions of Alkanes

59min

5.1.1. Summary Sheet: Common Organic Functional Groups

5.1.2. Example: Functional Groups 2 min

5.2.1. Drawing Organic Compouds in 2D2 min

5.2.2. Example: 2-D Notation2 min

5.2.3. Example: 2-D Notation1 min

5.2.4. Summary Sheet: Representing Molecules in Different 2D Notation

5.2.5. Summary Sheet: Condensed Formula

5.3.1. Drawing Organic Compounds in 3D5 min

5.3.2. Example: 3-D Notation2 min

5.3.3. Example: 3-D Notation2 min

5.3.4. Summary Sheet: Drawing in 3-Dimensions

5.4.1. Chair Conformations4 min

5.4.2. Example: Chair Conformations60 sec

5.4.3. Example: Chair Conformations1 min

5.4.4. Practice: Chair Conformations2 min

5.5.1. IUPAC Systematic Naming Theory15 min

5.5.2. Example: Converting Names to Structures2 min

5.5.3. Example: IUPAC Systematic Naming2 min

5.5.4. Example: IUPAC Systematic Naming2 min

5.5.5. Practice: IUPAC Systematic Naming2 min

5.5.6. Practice: IUPAC Systematic Naming2 min

5.5.7. Summary Sheet: IUPAC Naming

5.6.1. Summary Sheet: IUPAC Naming

5.6.2. Summary Sheet: Naming Molecules with Stereochemistry

5.6.3. Example: Naming Molecules with Stereochemistry4 min

5.6.4. Example: Naming Molecules with Stereochemistry2 min

5.6.5. Practice: Naming Molecules with Stereochemistry2 min

5.7.1. Enthalpy

5.7.3. Gibbs Free Energy

5.7.4. Activated Complex Theory

5.7.5. Chemical Kinetics

5.7.6. Activation Energy and Chemical Kine

5.8.1. Alkane Cracking

6. Unimolecular Reactions (SN1 and E1)

42min

6.1.1. General Terminology4 min

6.1.2. Nucleophiles4 min

6.1.3. Electrophiles2 min

6.1.4. Leaving Groups4 min

6.1.5. Substitution vs. Elimination2 min

6.1.6. Example: Substitution vs. Elimination3 min

6.2.1. Molecularity and Rate57 sec

6.2.2. Structural Requirements1 min

6.2.3. SN1 Mechanism4 min

6.2.4. Practice: Sn1 Reaction1 min

6.3.1. Stereochemistry in Substitution Reactions2 min

6.4.1. Leaving Group Ability4 min

6.4.2. Example: Alcohol as a Leaving Group2 min

6.5.1. Solvent Effects in Substitution Reactions

6.6.1. Molecularity and Rate43 sec

6.6.2. Structural Requirements52 sec

6.6.3. E1 Mechanism3 min

6.7.1. Selectivity in Elimination Reactions - E1 Reactions4 min

6.8.1. Favouring Elimination over Subsitution

6.9.1. Summary Sheet: Substitution Reactions

6.9.2. Summary Sheet: Elimination Reactions

6.P.1. Practice: Substitution Question 1

7. Reactions of Alkenes

2.2hr

7.1.1. Hydrohalogenation9 min

7.1.2. Example: Hydrohalogenation4 min

7.1.3. Example: Hydrohalogenation4 min

7.2.1. Acid-catalyzed Hydration9 min

7.2.2. Example: Acid-catalyzed Hydration4 min

7.2.3. Example: Acid-catalyzed Hydration 23 min

7.3.1. Hydroboration/Oxidation8 min

7.3.2. Example: Hydroboration 13 min

7.3.3. Example: Hydroboration 22 min

7.4.1. Halogenation13 min

7.4.2. Example: Halogenation 13 min

7.4.3. Example: Halogenation 22 min

7.4.4. Example: Halogenation3 min

7.5.1. Ozonolysis9 min

7.5.2. Example: Ozonolysis 12 min

7.5.3. Example: Ozonolysis4 min

7.6.1. Dihydroxylation5 min

7.6.2. Example: Dihydroxylation3 min

7.7.1. Epoxidation8 min

7.7.2. Example: Epoxidation3 min

7.7.3. Example: Epoxides as Electrophiles8 min

7.8.1. Hydrogenation6 min

7.8.2. Example: Hydrogenation 13 min

7.8.3. Example: Hydrogenation 22 min

7.8.4. Example: Hydrogenation 31 min

7.8.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

7.9.1. Carbocation Rearrangements6 min

7.9.2. Example: Carbocation Rearrangements3 min

7.9.3. Example: Carbocation Rearrangements3 min

7.10.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

7.P.1. Practice: Reaction Energy Diagrams

8. Reactions of Alkynes

8.1.1. Preparation of Alkynes from Vicinal Dihalides

8.1.2. Preparation of Alkynes from Geminal Dihalides

8.1.3. C-C Bond Formation Using Terminal Alkynes

8.2.1. Hydrogenation of Alkynes (Review)

8.2.2. Hydrohalogenation of Alkynes

8.2.3. Hydrohalogenation of Alkynes with HBr and Peroxides

8.2.4. Mercury-Catalyzed Hydration of Alkynes

8.2.5. Hydroboration-Oxidation of Alkynes

8.2.6. Halogenation of Alkynes

8.2.7. Ozonolysis of Alkynes

9. Reactions of Aromatics

48min

9.1.1. Aromaticity13 min

9.1.2. Summary Sheet: Naming Aromatic Rings

9.1.3. Example: Aromaticity5 min

9.1.4. Example: Aromaticity3 min

9.1.5. Practice: Aromaticity2 min

9.2.1. Electrophilic Aromatic Substitution Reactions 8 min

9.2.2. Electrophilic Aromatic Substitution4 min

9.3.1. Considerations for Electrophilic Aromatic Substitutions6 min

9.3.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

9.3.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

9.4.1. Summary Sheet: Aromaticity and Related Reactions

9.4.2. Summary Sheet: Naming Aromatic Rings

10. Bimolecular Mechanisms (SN2 and E2)

1.4hr

10.1.1. General Terminology4 min

10.1.2. Nucleophiles4 min

10.1.3. Electrophiles2 min

10.1.4. Leaving Groups4 min

10.1.5. Substitution vs. Elimination2 min

10.1.6. Example: Substitution vs. Elimination3 min

10.2.1. Molecularity and Rate57 sec

10.2.2. Structural Requirements1 min

10.2.3. SN1 Mechanism4 min

10.2.4. Practice: Sn1 Reaction1 min

10.3.1. Molecularity and Rate1 min

10.3.2. Structural Requirements2 min

10.3.3. SN2 Mechanism4 min

10.3.4. Practice: Sn2 Reaction1 min

10.4.1. Stereochemistry in Substitution Reactions2 min

10.5.1. Leaving Group Ability4 min

10.5.2. Example: Alcohol as a Leaving Group2 min

10.6.1. Solvent Effects in Substitution Reactions6 min

10.7.1. Molecularity and Rate43 sec

10.7.2. Structural Requirements52 sec

10.7.3. E1 Mechanism3 min

10.8.1. Molecularity and Rate45 sec

10.8.2. Structural Requirements2 min

10.8.3. Synthesis of Alkynes1 min

10.8.4. E2 Mechanism3 min

10.9.1. Selectivity in Elimination Reactions - E2 Reactions8 min

10.9.2. Selectivity in Elimination Reactions - E1 Reactions4 min

10.9.3. Example: Selectivity in Elimination Reactions6 min

10.10.1. Favouring Elimination over Subsitution5 min

10.11.1. Summary Sheet: Substitution Reactions

10.11.2. Summary Sheet: Elimination Reactions

10.P.1. Practice: Substitution Question 1

10.P.2. Practice: Substitution Question 2

10.P.3. Practice: Elimination Question 1

10.P.4. Practice: Elimination Question 2

10.P.5. Practice: Elimination Question 3

11. Reactions of Alcohols

21min

11.1.1. Physical Properties and Naming

11.2.1. Alcohol Reactivity

11.3.1. SN1/SN2 Reactions of Alkyl Halides (Review)

11.3.2. Electrophilic Addition to Alkenes: Acid-catalyzed Hydration (Review)

11.3.3. Electrophilic Addition to Alkenes: Hydroboration/Oxidation (Review)

11.3.4. Electrophilic Addition to Alkenes: Dihydroxylation (Review)

11.3.5. Oxymercuration Reactions (Review)

11.4.1. Halogenation of Alcohols

11.4.2. Elimination of Alcohols to Alkenes

11.5.1. Overview of Ethers

11.5.2. Williamson Ether Synthesis8 min

11.5.3. Stereochemistry of Epoxide Formation and Opening13 min

12. Reactions of the Carbonyl Group

3hr

12.1.1. Nomenclature and Physical Properties3 min

12.2.1. General Reactivity1 min

12.2.2. General Mechanism at the Carbonyl4 min

12.3.1. The Grignard Reaction5 min

12.3.2. Cyanohydrin Formation3 min

12.3.3. Example: The Grignard Reaction2 min

12.3.4. Practice: The Grignard Reaction5 min

12.4.1. General Reactions with Oxygen Nucleophiles5 min

12.4.2. Hydrate Formation1 min

12.4.3. Acetal Formation2 min

12.4.4. Ketal Formation2 min

12.4.5. Hydrolysis of Acetals and Ketals3 min

12.4.6. General Mechanism with Oxygen Nucleophiles9 min

12.4.7. Stability of Hemiketals and Hemiacetals3 min

12.4.8. Practice: Ketals and Acetals as Protecting Groups2 min

12.4.9. Practice: Ketals and Acetals as Protecting Groups2 min

12.4.10. Example: Synthesis and Hydrolysis of Ketals and Acetals1 min

12.4.11. Practice: Mechanism in Acetal and Ketal Formation3 min

12.4.12. Practice: Identifying Acetals/Aldehydes2 min

12.5.1. Synthesis and Hydrolysis of Imines7 min

12.5.2. Enamine Formation2 min

12.5.3. Mechanism of Imiine Formation4 min

12.5.4. Reductive Amination2 min

12.5.5. Practice: Imine Formation2 min

12.6.1. Tautomerization8 min

12.6.2. Enolate Formation3 min

12.6.3. Kinetic vs. Thermodynamic Enolates5 min

12.6.4. The Aldol Reaction3 min

12.6.5. Mechanism of the Aldol Reaction5 min

12.6.6. The Retro-Aldol Reaction1 min

12.6.7. Mixed Aldol Reactions5 min

12.6.8. Example: The Aldol Reaction4 min

12.6.9. Practice: The Aldol Reaction2 min

12.7.1. Study Sheet: Reaction Overview and Key Ideas

12.8.1. Oxidation to make Aldehydes4 min

12.8.2. Oxidation to make Ketones2 min

12.8.3. Oxidation of Aldehydes3 min

12.8.4. Example: Oxidation Reactions5 min

12.9.1. Reduction using NaBH42 min

12.9.2. Reduction using LiAlH44 min

12.9.3. Example: Reduction Reactions3 min

12.9.4. Example: Reductions Reactions5 min

12.10.1. Hydrogenation6 min

12.10.2. Example: Hydrogenation3 min

12.10.3. Example: Hydrogenation2 min

12.10.4. Example: Hydrogenation1 min

12.10.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

12.11.1. Summary Sheet: Reduction and Oxidation Reactions

12.12.1. Carboxylic Acids2 min

12.12.2. Example: Carboxylic Acids5 min

12.12.3. Example: Carboxylic Acids2 min

12.13.1. Nomenclature and Physical Properties3 min

12.14.1. General Reactivity3 min

12.14.2. General Mechanism at the Carbonyl2 min

12.14.3. Practice: General Reactivity34 sec

12.14.4. Summary Sheet: Carboxylic Acid Reactivity

12.15.1. Acyl Halides3 min

12.15.2. Example: Acyl Halides2 min

12.15.3. Example: Acyl Halides 22 min

12.16.1. Synthesis of Anhydrides

12.16.2. Formation of Esters from Carboxylic Acids (Fisher Esterification)2 min

12.16.3. Other Syntheses of Esters1 min

12.16.4. Transesterification2 min

12.16.5. Example: Esters and Anhydrides9 min

12.16.6. Example: Esters and Anhydrides 28 min

12.17.1. Formation of Amides from Acid Halides1 min

12.17.2. Example: Amides3 min

12.17.3. Example: Amides2 min

12.17.4. Practice: Peptide Bonds50 sec

12.18.1. Hydrolysis of Acid Halides and Anhydrides38 sec

12.18.2. Hydrolysis of Esters and Amides24 sec

12.19.1. Nucleophilic Acyl Substitutions

Mock Exam

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