CHEM 2213A/B

UWO

Course Overview

Grade Boosters

Lessons & Practice

1. Anatomy of an Organic Molecule

1.6hr

1.1.1. Bonding Models

1.2.1. Lewis Structures and Formal Charges9 min

1.2.2. How to Draw Lewis Structures5 min

1.2.3. Example: Lewis Structures5 min

1.2.4. Example: Lewis Structures5 min

1.2.5. Practice: Lewis Structures2 min

1.2.6. Practice: Lewis Structures5 min

1.3.1. VSEPR Theory5 min

1.3.2. Example: VSEPR2 min

1.3.3. Example: VSEPR3 min

1.3.4. Practice: VSEPR4 min

1.4.1. Valence Bond Theory and Hybridization

1.4.2. Example: Valence Bond Theory/Hybridization

1.4.3. Practice: Valence Bond Theory/Hybridization

1.4.4. Practice: Hybridization7 min

1.4.5. Practice: Hybridization of Atoms in Methyldiazene58 sec

1.4.6. Hybridization: BH3

1.5.1. Bonding in Delocalized Systems3 min

1.5.2. Example: Resonance Structures6 min

1.5.3. Practice: Resonance8 min

1.5.4. Resonance Practice2 min

1.5.5. Resonance Structures: Stability

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. Organic Molecules as Acid-Base Reactions

56min

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

2.1.2. Key Definitions in Acids/Bases5 min

2.1.3. Acid/Base Equilibrium Constants2 min

2.1.4. Example: Acid/Base Arrows 3 min

2.2.1. Factors Influencing Acid/Base Strength2 min

2.2.2. Electronegativity1 min

2.2.3. Atom Size2 min

2.2.4. Resonance3 min

2.2.5. Hybridization3 min

2.2.6. Induction3 min

2.2.7. Aromaticity3 min

2.2.8. Example: Acid/Base Strength 3 min

2.2.9. Example: Acid/Base Strength 3 min

2.2.10. Practice: Acid/Base Equilibria 2 min

2.2.11. Practice: Acid/Base Equilibria 2 min

2.3.1. Important pKas You Should Know4 min

2.3.2. Relationship Between pH and pKa2 min

2.3.3. Amino Acids at Different pHs3 min

2.3.4. Practice: Amino Acids in Solution3 min

2.3.5. Practice: Amino Acids in Solution3 min

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

2.3.7. Summary Sheet: pKa's of Common Molecules

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

3. Fundamentals of Organic Structure: Molecular Conformations (Alkanes and Cycloalkanes)

50min

3.1.1. Summary Sheet: Common Organic Functional Groups

3.1.2. Example: Functional Groups 2 min

3.2.1. Drawing Organic Compouds in 2D2 min

3.2.2. Example: 2-D Notation2 min

3.2.3. Example: 2-D Notation1 min

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

3.2.5. Summary Sheet: Condensed Formula

3.3.1. Drawing Organic Compounds in 3D5 min

3.3.2. Example: 3-D Notation2 min

3.3.3. Example: 3-D Notation2 min

3.3.4. Summary Sheet: Drawing in 3-Dimensions

3.3.5. Conformational Analysis and Energetics

3.4.1. Chair Conformations4 min

3.4.2. Example: Chair Conformations60 sec

3.4.3. Example: Chair Conformations1 min

3.4.4. Practice: Chair Conformations2 min

3.5.1. IUPAC Systematic Naming Theory15 min

3.5.2. Example: Converting Names to Structures2 min

3.5.3. Example: IUPAC Systematic Naming2 min

3.5.4. Example: IUPAC Systematic Naming2 min

3.5.5. Practice: IUPAC Systematic Naming2 min

3.5.6. Practice: IUPAC Systematic Naming2 min

3.5.7. Summary Sheet: IUPAC Naming

4. Isomerism and Stereochemistry

1.5hr

4.1.1. Summary Sheet: Isomers Flowchart

4.2.1. Constitutional Isomers5 min

4.2.2. Example: Constitutional Isomers4 min

4.2.3. Example: Constitutional Isomers3 min

4.3.1. Conformational Isomers6 min

4.3.2. Example: Conformational Isomers3 min

4.4.1. Geometric or Cis/Trans Isomers6 min

4.4.2. Example: Geometric Isomers4 min

4.4.3. Practice: Geometric Isomers 2 min

4.5.1. Chiral Molecules5 min

4.5.2. Cahn-Ingold-Prelog Rules4 min

4.5.3. Assigning R and S Nomenclature4 min

4.5.4. Example: Stereochemistry7 min

4.5.5. Example: Stereochemistry 24 min

4.5.6. Practice: Stereochemistry 2 min

4.5.7. Practice: Stereochemistry1 min

4.6.1. Optical Isomers13 min

4.6.2. Example: Optical Isomers3 min

4.6.3. Example: Optical Isomers 23 min

4.6.4. Practice: Optical Isomers 1 min

4.7.1. Summary Sheet: IUPAC Naming

4.7.2. Summary Sheet: Naming Molecules with Stereochemistry

4.7.3. Example: Naming Molecules with Stereochemistry4 min

4.7.4. Example: Naming Molecules with Stereochemistry2 min

4.7.5. Practice: Naming Molecules with Stereochemistry2 min

4.8.1. Summary Sheet: Stereochemistry

4.8.2. Summary Sheet: Determining Maximum Number of Stereoisomers

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

5. Alkyl Halides and Nucleophilic Substitutions and Eliminations

1.4hr

5.1.1. General Terminology4 min

5.1.2. Nucleophiles4 min

5.1.3. Electrophiles2 min

5.1.4. Leaving Groups4 min

5.1.5. Substitution vs. Elimination2 min

5.1.6. Example: Substitution vs. Elimination3 min

5.2.1. Molecularity and Rate57 sec

5.2.2. Structural Requirements1 min

5.2.3. SN1 Mechanism4 min

5.2.4. Practice: Sn1 Reaction1 min

5.3.1. Molecularity and Rate1 min

5.3.2. Structural Requirements2 min

5.3.3. SN2 Mechanism4 min

5.3.4. Practice: Sn2 Reaction1 min

5.4.1. Stereochemistry in Substitution Reactions2 min

5.5.1. Leaving Group Ability4 min

5.5.2. Example: Alcohol as a Leaving Group2 min

5.6.1. Solvent Effects in Substitution Reactions6 min

5.7.1. Molecularity and Rate43 sec

5.7.2. Structural Requirements52 sec

5.7.3. E1 Mechanism3 min

5.8.1. Molecularity and Rate45 sec

5.8.2. Structural Requirements2 min

5.8.3. Synthesis of Alkynes1 min

5.8.4. E2 Mechanism3 min

5.9.1. Selectivity in Elimination Reactions - E2 Reactions8 min

5.9.2. Selectivity in Elimination Reactions - E1 Reactions4 min

5.9.3. Example: Selectivity in Elimination Reactions6 min

5.10.1. Favouring Elimination over Subsitution5 min

5.11.1. Summary Sheet: Substitution Reactions

5.11.2. Summary Sheet: Elimination Reactions

5.P.1. Practice: Substitution Question 2

5.P.2. Practice: Elimination Question 1

5.P.3. Practice: Elimination Question 2

6. Addition Reactions of Alkenes

2.2hr

6.1.1. Hydrohalogenation9 min

6.1.2. Example: Hydrohalogenation4 min

6.1.3. Example: Hydrohalogenation4 min

6.2.1. Acid-catalyzed Hydration9 min

6.2.2. Example: Acid-catalyzed Hydration4 min

6.2.3. Example: Acid-catalyzed Hydration 23 min

6.3.1. Hydroboration/Oxidation8 min

6.3.2. Example: Hydroboration 13 min

6.3.3. Example: Hydroboration 22 min

6.4.1. Halogenation13 min

6.4.2. Example: Halogenation 13 min

6.4.3. Example: Halogenation 22 min

6.4.4. Example: Halogenation3 min

6.5.1. Ozonolysis9 min

6.5.2. Example: Ozonolysis 12 min

6.5.3. Example: Ozonolysis4 min

6.6.1. Dihydroxylation5 min

6.6.2. Example: Dihydroxylation3 min

6.7.1. Epoxidation8 min

6.7.2. Example: Epoxidation3 min

6.7.3. Example: Epoxides as Electrophiles8 min

6.8.1. Hydrogenation6 min

6.8.2. Example: Hydrogenation 13 min

6.8.3. Example: Hydrogenation 22 min

6.8.4. Example: Hydrogenation 31 min

6.8.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

6.9.1. Carbocation Rearrangements6 min

6.9.2. Example: Carbocation Rearrangements3 min

6.9.3. Example: Carbocation Rearrangements3 min

6.10.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

6.P.1. Practice: Reaction Energy Diagrams

7. Aromaticity and Electrophilic Aromatic Substitution

48min

7.1.1. Aromaticity13 min

7.1.2. Summary Sheet: Naming Aromatic Rings

7.1.3. Example: Aromaticity5 min

7.1.4. Example: Aromaticity3 min

7.1.5. Practice: Aromaticity2 min

7.2.1. Electrophilic Aromatic Substitution Reactions 8 min

7.2.2. Electrophilic Aromatic Substitution4 min

7.3.1. Considerations for Electrophilic Aromatic Substitutions6 min

7.3.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

7.3.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

7.4.1. Summary Sheet: Aromaticity and Related Reactions

7.4.2. Summary Sheet: Naming Aromatic Rings

8. Alcohols and Phenols Reactivity

59min

8.1.1. Physical Properties and Naming

8.2.1. Alcohol Reactivity

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

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

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

8.3.4. Electrophilic Addition to Alkenes: Dihydroxylation (Review)

8.3.5. Nomenclature and Physical Properties of Aldehydes and Ketones (Brief Introduction)

8.3.6. General Reactivity of Aldehydes and Ketones (Brief Introduction)1 min

8.3.7. General Mechanism at the Carbonyl4 min

8.3.8. Reduction of Aldehydes and Ketones using NaBH42 min

8.3.9. Reduction of any Carbonyl using LiAlH44 min

8.3.10. Example: Reduction Reactions3 min

8.3.11. Example: Reductions Reactions5 min

8.3.12. The Grignard Reaction5 min

8.3.13. Example: The Grignard Reaction2 min

8.3.14. Practice: The Grignard Reaction5 min

8.3.15. Study Sheet: Reaction Overview and Key Ideas

8.4.1. Halogenation of Alcohols

8.4.2. Elimination of Alcohols to Alkenes

8.4.3. Oxidation of Primary Alcohols to make Aldehydes

8.4.4. Oxidation to make Ketones

8.4.5. Example: Oxidation Reactions5 min

8.5.1. Overview of Ethers

8.5.2. Williamson Ether Synthesis8 min

8.5.3. Stereochemistry of Epoxide Formation and Opening13 min

8.6.1. Physical Properties

8.6.2. Formation of Thiols via Substitution of Alkyl Halides

8.6.3. Oxidation of Thiols

8.6.4. Formation of Sulfides via Substitution of Alkyl Halides

8.6.5. Oxidation of Sulfides

9. Structure Elucidation: IR, 13C-NMR, 1H-NMR

1.9hr

9.1.1. Hydrogen Deficiency Index4 min

9.2.1. Infrared Spectroscopy12 min

9.2.2. Example: IR Spectroscopy2 min

9.2.3. Example: IR Spectroscopy52 sec

9.2.4. Practice Question: IR Spectroscopy1 min

9.2.5. Practice Question: IR Spectroscopy 21 min

9.3.1. Mass Spectrometry9 min

9.3.2. Example: Mass Spectrometry4 min

9.3.3. Example: Mass Spectrometry2 min

9.3.4. Example: Mass Spectrometry2 min

9.4.1. NMR Theory6 min

9.4.2. Example: Intro to NMR2 min

9.4.3. Example: Intro to NMR2 min

9.5.1. Hydrogen (1H NMR)20 min

9.5.2. Example: 1H NMR3 min

9.5.3. Example: 1H NMR6 min

9.5.4. Practice: 1H NMR 3 min

9.5.5. Practice Question: 1H NMR2 min

9.5.6. Practice Question: 1H NMR1 min

9.5.7. Practice Question4 min

9.6.1. Carbon (13C) NMR8 min

9.6.2. Example: 13C NMR3 min

9.6.3. Example: 13C NMR4 min

9.6.4. Practice: 13C NMR3 min

9.6.5. Example: 13C NMR3 min

9.7.1. Structure Elucidation

9.P.1. Practice: Structure Elucidation 1

9.P.2. Practice: Structure Elucidation 2

9.P.3. Practice: Structure Elucidation 3

10. Chemistry of Aldehydes and Ketones

2.3hr

10.1.1. Nomenclature and Physical Properties3 min

10.2.1. Oxidation to make Aldehydes4 min

10.2.2. Oxidation to make Ketones2 min

10.2.3. Oxidation of Aldehydes3 min

10.2.4. Example: Oxidation Reactions5 min

10.3.1. Reduction using NaBH42 min

10.3.2. Reduction using LiAlH44 min

10.3.3. Example: Reduction Reactions3 min

10.3.4. Example: Reductions Reactions5 min

10.4.1. Summary Sheet: Reduction and Oxidation Reactions

10.5.1. General Reactivity1 min

10.5.2. General Mechanism at the Carbonyl4 min

10.6.1. The Grignard Reaction5 min

10.6.2. Cyanohydrin Formation3 min

10.6.3. Example: The Grignard Reaction2 min

10.6.4. Practice: The Grignard Reaction5 min

10.7.1. General Reactions with Oxygen Nucleophiles5 min

10.7.2. Hydrate Formation1 min

10.7.3. Acetal Formation2 min

10.7.4. Ketal Formation2 min

10.7.5. Hydrolysis of Acetals and Ketals3 min

10.7.6. General Mechanism with Oxygen Nucleophiles9 min

10.7.7. Stability of Hemiketals and Hemiacetals3 min

10.7.8. Practice: Ketals and Acetals as Protecting Groups2 min

10.7.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

10.7.11. Practice: Mechanism in Acetal and Ketal Formation3 min

10.7.12. Practice: Reagents in Acetal and Ketal Chemistry

10.7.13. Practice: Identifying Acetals/Aldehydes2 min

10.8.1. Synthesis and Hydrolysis of Imines7 min

10.8.2. Enamine Formation2 min

10.8.3. Mechanism of Imiine Formation4 min

10.8.4. Reductive Amination2 min

10.8.5. Practice: Imine Formation2 min

10.9.1. Tautomerization8 min

10.9.2. Enolate Formation3 min

10.9.3. Kinetic vs. Thermodynamic Enolates5 min

10.9.4. The Aldol Reaction3 min

10.9.5. Mechanism of the Aldol Reaction5 min

10.9.6. The Retro-Aldol Reaction1 min

10.9.7. Mixed Aldol Reactions5 min

10.9.8. Example: The Aldol Reaction4 min

10.9.9. Practice: The Aldol Reaction2 min

10.10.1. Study Sheet: Reaction Overview and Key Ideas

11. Carboxylic Acids and Derivatives

1.1hr

11.1.1. Carboxylic Acids2 min

11.1.2. Example: Carboxylic Acids5 min

11.1.3. Example: Carboxylic Acids2 min

11.2.1. Nomenclature and Physical Properties3 min

11.3.1. General Reactivity3 min

11.3.2. General Mechanism at the Carbonyl2 min

11.3.3. Practice: General Reactivity34 sec

11.3.4. Summary Sheet: Carboxylic Acid Reactivity

11.4.1. Acyl Halides3 min

11.4.2. Example: Acyl Halides2 min

11.4.3. Example: Acyl Halides 22 min

11.5.1. Synthesis of Anhydrides

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

11.5.3. Other Syntheses of Esters1 min

11.5.4. Transesterification2 min

11.5.5. Example: Esters and Anhydrides9 min

11.5.6. Example: Esters and Anhydrides 28 min

11.6.1. Formation of Amides from Acid Halides1 min

11.6.2. Example: Amides3 min

11.6.3. Example: Amides2 min

11.6.4. Practice: Peptide Bonds50 sec

11.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

11.7.2. Hydrolysis of Esters and Amides24 sec

11.8.1. Claisen Reactions3 min

11.8.2. Example: Claisen Reactions4 min

11.8.3. Example: Claisen Reactions2 min

11.8.4. Example: Dieckmann Condensation3 min

11.9.1. Nucleophilic Acyl Substitutions

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ME.2. Final Exam - Mock Assessment91 Qns

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