CHM136H1

U of T

Course Overview

Lessons & Practice

I. Welcome

1. Shape and Drawing; Bonding - Hybridization & Bonding - Resonance

1.5hr

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. Bonding in Delocalized Systems3 min

1.4.2. Example: Resonance Structures6 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

1.Q. Checkpoint Quiz9 Qns

2. Acid - Base Reaction

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

2.Q. Checkpoint Quiz15 Qns

3. Naming Alkanes & Conformations

1hr

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

3.4.1. Converting Fischer Structures4 min

3.4.2. Example: Converting Fischer Structures3 min

3.4.3. Example: Converting Fischer Structures3 min

3.4.4. Practice Question: Converting Fischer Projections2 min

3.5.1. Chair Conformations4 min

3.5.2. Example: Chair Conformations60 sec

3.5.3. Example: Chair Conformations1 min

3.5.4. Practice: Chair Conformations2 min

3.6.1. IUPAC Systematic Naming Theory15 min

3.6.2. Example: Converting Names to Structures2 min

3.6.3. Example: IUPAC Systematic Naming2 min

3.6.4. Example: IUPAC Systematic Naming2 min

3.6.5. Practice: IUPAC Systematic Naming2 min

3.6.6. Practice: IUPAC Systematic Naming2 min

3.6.7. Summary Sheet: IUPAC Naming

3.Q. Checkpoint Quiz15 Qns

4. Stereochemistry & Isomers

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

4.Q. Checkpoint Quiz10 Qns

5. Electrophilic Addition Reactions to Alkenes/Alkynes

2.3hr

5.1.1. Hydrohalogenation9 min

5.1.2. Example: Hydrohalogenation4 min

5.1.3. Example: Hydrohalogenation4 min

5.2.1. Acid-catalyzed Hydration9 min

5.2.2. Example: Acid-catalyzed Hydration4 min

5.2.3. Example: Acid-catalyzed Hydration 23 min

5.3.1. Hydroboration/Oxidation8 min

5.3.2. Example: Hydroboration 13 min

5.3.3. Example: Hydroboration 22 min

5.4.1. Halogenation13 min

5.4.2. Example: Halogenation 13 min

5.4.3. Example: Halogenation 22 min

5.4.4. Example: Halogenation3 min

5.5.1. Ozonolysis9 min

5.5.2. Example: Ozonolysis 12 min

5.5.3. Example: Ozonolysis4 min

5.6.1. Dihydroxylation5 min

5.6.2. Example: Dihydroxylation3 min

5.7.1. Epoxidation8 min

5.7.2. Example: Epoxidation3 min

5.7.3. Example: Epoxides as Electrophiles8 min

5.8.1. Hydrogenation6 min

5.8.2. Example: Hydrogenation 13 min

5.8.3. Example: Hydrogenation 22 min

5.8.4. Example: Hydrogenation 31 min

5.8.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

5.9.1. Carbocation Rearrangements6 min

5.9.2. Example: Carbocation Rearrangements3 min

5.9.3. Example: Carbocation Rearrangements3 min

5.10.1. Terpene Biosynthesis2 min

5.10.2. Example: Terpene Biosynthesis 12 min

5.10.3. Example: Terpene Biosynthesis4 min

5.11.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

5.Q. Checkpoint Quiz9 Qns

5.P.1. Practice: Reaction Energy Diagrams

6. Organohalides (Radical Halogenation Reactions)

30min

6.1.1. Radical Stability4 min

6.1.2. Example: Radical Stability3 min

6.1.3. Example: Radical Stability1 min

6.1.4. Practice: Radical Stability1 min

6.2.1. Radical Reactions: Radical Halogenation7 min

6.2.2. Radical Reactions: Hydrohalogenation with a Peroxide7 min

6.2.3. Practice: Radical Reactions2 min

6.2.4. Practice: Radical Reactions2 min

6.2.5. Practice: Radical Reactions3 min

6.3.1. Summary Sheet: Radical Reactions

6.Q. Checkpoint Quiz7 Qns

7. Nucleophilic Substitutions and Elimination Reactions

1.4hr

7.1.1. General Terminology4 min

7.1.2. Nucleophiles4 min

7.1.3. Electrophiles2 min

7.1.4. Leaving Groups4 min

7.1.5. Substitution vs. Elimination2 min

7.1.6. Example: Substitution vs. Elimination3 min

7.2.1. Molecularity and Rate57 sec

7.2.2. Structural Requirements1 min

7.2.3. SN1 Mechanism4 min

7.2.4. Practice: Sn1 Reaction1 min

7.3.1. Molecularity and Rate1 min

7.3.2. Structural Requirements2 min

7.3.3. SN2 Mechanism4 min

7.3.4. Practice: Sn2 Reaction1 min

7.4.1. Stereochemistry in Substitution Reactions2 min

7.5.1. Leaving Group Ability4 min

7.5.2. Example: Alcohol as a Leaving Group2 min

7.6.1. Solvent Effects in Substitution Reactions6 min

7.7.1. Molecularity and Rate43 sec

7.7.2. Structural Requirements52 sec

7.7.3. E1 Mechanism3 min

7.8.1. Molecularity and Rate45 sec

7.8.2. Structural Requirements2 min

7.8.3. Synthesis of Alkynes1 min

7.8.4. E2 Mechanism3 min

7.9.1. Selectivity in Elimination Reactions - E2 Reactions8 min

7.9.2. Selectivity in Elimination Reactions - E1 Reactions4 min

7.9.3. Example: Selectivity in Elimination Reactions6 min

7.10.1. Favouring Elimination over Subsitution5 min

7.11.1. Summary Sheet: Substitution Reactions

7.11.2. Summary Sheet: Elimination Reactions

7.Q. Checkpoint Quiz13 Qns

7.P.1. Practice: Substitution Question 1

7.P.2. Practice: Substitution Question 2

7.P.3. Practice: Elimination Question 1

7.P.4. Practice: Elimination Question 2

7.P.5. Practice: Elimination Question 3

8. Aromaticity (Arenes)

23min

8.1.1. Aromaticity13 min

8.1.2. Summary Sheet: Naming Aromatic Rings

8.1.3. Example: Aromaticity5 min

8.1.4. Example: Aromaticity3 min

8.1.5. Practice: Aromaticity2 min

8.2.1. Summary Sheet: Naming Aromatic Rings

8.Q. Checkpoint Quiz4 Qns

9. Infrared Spectroscopy

22min

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. Structure Elucidation

10. Alcohol Reactions (Reduction/Oxidation)

42min

10.1.1. Reduction using NaBH42 min

10.1.2. Reduction using LiAlH44 min

10.1.3. Example: Reduction Reactions3 min

10.1.4. Example: Reductions Reactions5 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. Hydrogenation6 min

10.3.2. Example: Hydrogenation3 min

10.3.3. Example: Hydrogenation2 min

10.3.4. Example: Hydrogenation1 min

10.3.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

10.4.1. Summary Sheet: Reduction and Oxidation Reactions

10.Q. Checkpoint Quiz7 Qns

11. Oxidized Alcohols - Reactivity with Aldehydes and Ketones

1.3hr

11.1.1. Nomenclature and Physical Properties3 min

11.2.1. General Reactivity1 min

11.2.2. General Mechanism at the Carbonyl4 min

11.3.1. The Grignard Reaction5 min

11.3.2. Cyanohydrin Formation3 min

11.3.3. Example: The Grignard Reaction2 min

11.3.4. Practice: The Grignard Reaction5 min

11.4.1. General Reactions with Oxygen Nucleophiles5 min

11.4.2. Hydrate Formation1 min

11.4.3. Acetal Formation2 min

11.4.4. Ketal Formation2 min

11.4.5. Hydrolysis of Acetals and Ketals3 min

11.4.6. General Mechanism with Oxygen Nucleophiles9 min

11.4.7. Stability of Hemiketals and Hemiacetals3 min

11.4.8. Practice: Ketals and Acetals as Protecting Groups2 min

11.4.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

11.4.11. Practice: Mechanism in Acetal and Ketal Formation3 min

11.4.12. Practice: Identifying Acetals/Aldehydes2 min

11.5.1. Synthesis and Hydrolysis of Imines7 min

11.5.2. Enamine Formation2 min

11.5.3. Mechanism of Imiine Formation4 min

11.5.4. Reductive Amination2 min

11.5.5. Practice: Imine Formation2 min

12. Oxidized Alcohols - Reactivity with Carboxylic Acid Derivatives (Nucleophilic Acyl Substitutions)

53min

12.1.1. Carboxylic Acids2 min

12.1.2. Example: Carboxylic Acids5 min

12.1.3. Example: Carboxylic Acids2 min

12.2.1. Nomenclature and Physical Properties3 min

12.3.1. General Reactivity3 min

12.3.2. General Mechanism at the Carbonyl2 min

12.3.3. Practice: General Reactivity34 sec

12.3.4. Summary Sheet: Carboxylic Acid Reactivity

12.4.1. Acyl Halides3 min

12.4.2. Example: Acyl Halides2 min

12.4.3. Example: Acyl Halides 22 min

12.5.1. Synthesis of Anhydrides

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

12.5.3. Other Syntheses of Esters1 min

12.5.4. Transesterification2 min

12.5.5. Example: Esters and Anhydrides9 min

12.5.6. Example: Esters and Anhydrides 28 min

12.6.1. Formation of Amides from Acid Halides1 min

12.6.2. Example: Amides3 min

12.6.3. Example: Amides2 min

12.6.4. Practice: Peptide Bonds50 sec

12.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

12.7.2. Hydrolysis of Esters and Amides24 sec

12.8.1. Nucleophilic Acyl Substitutions

12.Q. Checkpoint Quiz13 Qns

Mock Exams

ME.1. Test 1 - Mock Assessment31 Qns

ME.2. Test 2 - Mock Assessment14 Qns

ME.3. Final Exam - Mock Assessment23 Qns

ME.2 Test 2 - Mock Assessment

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