CHEM 266

UWaterloo

Course Overview

Lessons & Practice

I. Welcome

1. Module 1 (Nomenclature)

41min

1.1.1. Summary Sheet: Common Organic Functional Groups

1.1.2. Example: Functional Groups 2 min

1.2.1. Drawing Organic Compouds in 2D2 min

1.2.2. Example: 2-D Notation2 min

1.2.3. Example: 2-D Notation1 min

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

1.2.5. Summary Sheet: Condensed Formula

1.3.1. Drawing Organic Compounds in 3D5 min

1.3.2. Example: 3-D Notation2 min

1.3.3. Example: 3-D Notation2 min

1.3.4. Summary Sheet: Drawing in 3-Dimensions

1.4.1. IUPAC Systematic Naming Theory15 min

1.4.2. Example: Converting Names to Structures2 min

1.4.3. Example: IUPAC Systematic Naming2 min

1.4.4. Example: IUPAC Systematic Naming2 min

1.4.5. Practice: IUPAC Systematic Naming2 min

1.4.6. Practice: IUPAC Systematic Naming2 min

1.4.7. Summary Sheet: IUPAC Naming

2. Module 2 (Structure of Atoms)

1.1hr

2.1.1. Lewis Structures and Formal Charges9 min

2.1.2. How to Draw Lewis Structures5 min

2.1.3. Example: Lewis Structures5 min

2.1.4. Example: Lewis Structures5 min

2.1.5. Practice: Lewis Structures2 min

2.1.6. Practice: Lewis Structures5 min

2.2.1. VSEPR Theory5 min

2.2.2. Example: VSEPR2 min

2.2.3. Example: VSEPR3 min

2.2.4. Practice: VSEPR4 min

2.3.1. Polar Bonds6 min

2.3.2. Example: Polar Bonds3 min

2.3.3. Example: Polar Bonds 2 min

2.3.4. Practice: Polar Bonds 50 sec

2.4.1. Intermolecular Forces4 min

2.4.2. Melting and Boiling Point Comparison4 min

2.4.3. Example: Intermolecular Forces3 min

2.4.4. Example: Intermolecular Forces2 min

2.4.5. Practice: Intermolecular Forces1 min

2.5.1. Summary Sheet: The Basics

2.Q. Checkpoint Quiz9 Qns

3. Module 3 (Orbitals)

20min

3.1.1. Bonding Models

3.1.2. Practice: Valence Bond Theory/Hybridization3 min

3.2.1. Valence Bond Theory and Hybridization7 min

3.2.2. Example: Valence Bond Theory/Hybridization5 min

3.3.1. Molecular Orbital Theory4 min

4. Module 4 (Resonance)

10min

4.1.1. Bonding in Delocalized Systems3 min

4.1.2. Example: Resonance Structures6 min

5. Module 5 (Physical Properties)

1.9hr

5.1.1. Intramolecular vs Intermolecular Forces5 min

5.1.2. Intermolecular Forces Theory15 min

5.1.5. Practice9 min

5.2.1. Phases of Matter3 min

5.3.1. Types of Intermolecular Forces (more detailed version)9 min

5.3.2. Strength of Intermolecular Forces Cheatsheet

5.3.3. Example4 min

5.3.4. Example4 min

5.3.5. Practice

5.3.6. Practice

5.4.1. Phases of Matter3 min

5.4.2. Intermolecular Forces and Boiling Point11 min

5.4.3. Other Physical Properties and Intermolecular Forces6 min

5.4.4. Example9 min

5.4.5. Example4 min

5.4.6. Practice

5.4.7. Practice

5.5.1. Viscosity 5 min

5.5.2. Surface Tension6 min

5.5.3. Capillary Action10 min

5.5.4. Example4 min

5.5.6. Practice

5.5.7. Practice 8 min

5.6.1. Vapour Pressure Equation

5.6.2. Practice

6. Module 6 (Acids and Bases)

56min

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

6.1.2. Key Definitions in Acids/Bases5 min

6.1.3. Acid/Base Equilibrium Constants2 min

6.1.4. Example: Acid/Base Arrows 3 min

6.2.1. Factors Influencing Acid/Base Strength2 min

6.2.2. Electronegativity1 min

6.2.3. Atom Size2 min

6.2.4. Resonance3 min

6.2.5. Hybridization3 min

6.2.6. Induction3 min

6.2.7. Aromaticity3 min

6.2.8. Example: Acid/Base Strength 3 min

6.2.9. Example: Acid/Base Strength 3 min

6.2.10. Practice: Acid/Base Equilibria 2 min

6.2.11. Practice: Acid/Base Equilibria 2 min

6.3.1. Important pKas You Should Know4 min

6.3.2. Relationship Between pH and pKa2 min

6.3.3. Amino Acids at Different pHs3 min

6.3.4. Practice: Amino Acids in Solution3 min

6.3.5. Practice: Amino Acids in Solution3 min

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

6.3.7. Summary Sheet: pKa's of Common Molecules

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

6.Q. Checkpoint Quiz15 Qns

7. Module 7 (Conformations and Stereochemistry)

1.8hr

7.1.1. Summary Sheet: Isomers Flowchart

7.2.1. Constitutional Isomers5 min

7.2.2. Example: Constitutional Isomers4 min

7.2.3. Example: Constitutional Isomers3 min

7.3.1. Conformational Isomers6 min

7.3.2. Example: Conformational Isomers3 min

7.4.1. Geometric or Cis/Trans Isomers6 min

7.4.2. Example: Geometric Isomers4 min

7.4.3. Practice: Geometric Isomers 2 min

7.5.1. Chiral Molecules5 min

7.5.2. Cahn-Ingold-Prelog Rules4 min

7.5.3. Assigning R and S Nomenclature4 min

7.5.4. Example: Stereochemistry7 min

7.5.5. Example: Stereochemistry 24 min

7.5.6. Practice: Stereochemistry 2 min

7.5.7. Practice: Stereochemistry1 min

7.6.1. Optical Isomers13 min

7.6.2. Example: Optical Isomers3 min

7.6.3. Example: Optical Isomers 23 min

7.6.4. Practice: Optical Isomers 1 min

7.7.1. Chair Conformations4 min

7.7.2. Example: Chair Conformations60 sec

7.7.3. Example: Chair Conformations1 min

7.7.4. Practice: Chair Conformations2 min

7.8.1. Converting Fischer Structures4 min

7.8.2. Example: Converting Fischer Structures3 min

7.8.3. Example: Converting Fischer Structures3 min

7.8.4. Practice Question: Converting Fischer Projections2 min

7.9.1. Summary Sheet: IUPAC Naming

7.9.2. Summary Sheet: Naming Molecules with Stereochemistry

7.9.3. Example: Naming Molecules with Stereochemistry4 min

7.9.4. Example: Naming Molecules with Stereochemistry2 min

7.9.5. Practice: Naming Molecules with Stereochemistry2 min

7.10.1. Summary Sheet: Stereochemistry

7.10.2. Summary Sheet: Determining Maximum Number of Stereoisomers

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

7.Q. Checkpoint Quiz10 Qns

8. Module 8 (Chemical Reactivity and Reaction Mechanisms)

21min

8.I. Chapter Intro10 min

8.1.1. Reaction Mechanisms10 min

8.2.1. Chemical Reactions Theory49 sec

9. Module 9 (Substitution Reactions)

48min

9.1.1. General Terminology4 min

9.1.2. Nucleophiles4 min

9.1.3. Electrophiles2 min

9.1.4. Leaving Groups4 min

9.1.5. Substitution vs. Elimination2 min

9.1.6. Example: Substitution vs. Elimination3 min

9.2.1. Molecularity and Rate57 sec

9.2.2. Structural Requirements1 min

9.2.3. SN1 Mechanism4 min

9.2.4. Practice: Sn1 Reaction1 min

9.3.1. Molecularity and Rate1 min

9.3.2. Structural Requirements2 min

9.3.3. SN2 Mechanism4 min

9.3.4. Practice: Sn2 Reaction1 min

9.4.1. Stereochemistry in Substitution Reactions2 min

9.5.1. Leaving Group Ability4 min

9.5.2. Example: Alcohol as a Leaving Group2 min

9.6.1. Solvent Effects in Substitution Reactions6 min

9.7.1. Summary Sheet: Substitution Reactions

10. Module 10 (Elimination Reactions)

34min

10.1.1. Molecularity and Rate43 sec

10.1.2. Structural Requirements52 sec

10.1.3. E1 Mechanism3 min

10.2.1. Molecularity and Rate45 sec

10.2.2. Structural Requirements2 min

10.2.3. Synthesis of Alkynes1 min

10.2.4. E2 Mechanism3 min

10.3.1. Selectivity in Elimination Reactions - E2 Reactions8 min

10.3.2. Selectivity in Elimination Reactions - E1 Reactions4 min

10.3.3. Example: Selectivity in Elimination Reactions6 min

10.4.1. Favouring Elimination over Subsitution5 min

10.5.1. Summary Sheet: Elimination Reactions

10.Q. Checkpoint Quiz13 Qns

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. Module 11 (Alkenes and Alkynes)

2.3hr

11.1.1. Hydrohalogenation9 min

11.1.2. Example: Hydrohalogenation4 min

11.1.3. Example: Hydrohalogenation4 min

11.2.1. Acid-catalyzed Hydration9 min

11.2.2. Example: Acid-catalyzed Hydration4 min

11.2.3. Example: Acid-catalyzed Hydration 23 min

11.3.1. Hydroboration/Oxidation8 min

11.3.2. Example: Hydroboration 13 min

11.3.3. Example: Hydroboration 22 min

11.4.1. Halogenation13 min

11.4.2. Example: Halogenation 13 min

11.4.3. Example: Halogenation 22 min

11.4.4. Example: Halogenation3 min

11.5.1. Ozonolysis9 min

11.5.2. Example: Ozonolysis 12 min

11.5.3. Example: Ozonolysis4 min

11.6.1. Dihydroxylation5 min

11.6.2. Example: Dihydroxylation3 min

11.7.1. Epoxidation8 min

11.7.2. Example: Epoxidation3 min

11.7.3. Example: Epoxides as Electrophiles8 min

11.8.1. Hydrogenation6 min

11.8.2. Example: Hydrogenation 13 min

11.8.3. Example: Hydrogenation 22 min

11.8.4. Example: Hydrogenation 31 min

11.8.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

11.9.1. Carbocation Rearrangements6 min

11.9.2. Example: Carbocation Rearrangements3 min

11.9.3. Example: Carbocation Rearrangements3 min

11.10.1. Reactivity of Dienes (*coming soon)

11.10.2. 1,2- and 1,4-addition of HX to dienes (*coming soon)

11.12.1. Terpene Biosynthesis2 min

11.12.2. Example: Terpene Biosynthesis 12 min

11.12.3. Example: Terpene Biosynthesis4 min

11.13.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

11.Q. Checkpoint Quiz9 Qns

11.P.1. Practice: Reaction Energy Diagrams

12. Module 12 (Alcohols)

3hr

12.1.1. SN1/SN2 - Alcohol as a Leaving Group11 min

12.2.1. General Reactions with Oxygen Nucleophiles5 min

12.2.2. Hydrate Formation1 min

12.2.3. Acetal Formation2 min

12.2.4. Ketal Formation2 min

12.2.5. Hydrolysis of Acetals and Ketals3 min

12.2.6. General Mechanism with Oxygen Nucleophiles9 min

12.2.7. Stability of Hemiketals and Hemiacetals3 min

12.2.8. Practice: Ketals and Acetals as Protecting Groups2 min

12.2.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

12.2.11. Practice: Mechanism in Acetal and Ketal Formation3 min

12.2.12. Practice: Identifying Acetals/Aldehydes2 min

12.3.1. Oxidation to make Aldehydes4 min

12.3.2. Oxidation to make Ketones2 min

12.3.3. Oxidation of Aldehydes3 min

12.3.4. Example: Oxidation Reactions5 min

12.4.1. Carboxylic Acids2 min

12.4.2. Example: Carboxylic Acids5 min

12.4.3. Example: Carboxylic Acids2 min

12.5.1. Nomenclature and Physical Properties3 min

12.6.1. General Reactivity3 min

12.6.2. General Mechanism at the Carbonyl2 min

12.6.3. Practice: General Reactivity34 sec

12.6.4. Summary Sheet: Carboxylic Acid Reactivity

12.7.1. Synthesis of Anhydrides

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

12.7.3. Other Syntheses of Esters1 min

12.7.4. Transesterification2 min

12.7.5. Example: Esters and Anhydrides9 min

12.7.6. Example: Esters and Anhydrides 28 min

12.8.1. The Grignard Reaction5 min

12.8.2. Cyanohydrin Formation3 min

12.8.3. Example: The Grignard Reaction2 min

12.8.4. Practice: The Grignard Reaction5 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. Synthesis and Hydrolysis of Imines7 min

12.10.2. Enamine Formation2 min

12.10.3. Mechanism of Imiine Formation4 min

12.10.4. Reductive Amination2 min

12.10.5. Practice: Imine Formation2 min

12.11.1. Tautomerization8 min

12.11.2. Enolate Formation3 min

12.11.3. Kinetic vs. Thermodynamic Enolates5 min

12.11.4. The Aldol Reaction3 min

12.11.5. Mechanism of the Aldol Reaction5 min

12.11.6. The Retro-Aldol Reaction1 min

12.11.7. Mixed Aldol Reactions5 min

12.11.8. Example: The Aldol Reaction4 min

12.11.9. Practice: The Aldol Reaction2 min

12.12.1. Study Sheet: Reaction Overview and Key Ideas

12.Q. Checkpoint Quiz4 Qns

13. Module 13 (Ethers, Epoxides and Sulfur Compounds))

48min

13.1.1. Nomenclature

13.2.1. Williamson Ether Synthesis8 min

13.3.1. Stereochemistry of Epoxide Formation and Opening13 min

13.3.2. Example: Epoxides as Electrophiles6 min

13.3.3. Opening of Epoxides with Grignard Reagent4 min

13.3.4. SN1 and SN2 Reactions with Epoxides

13.3.5. Choice of Electrophile in Substitution Reactions14 min

13.4.1. Reaction of Thiols with Carbonyls5 min

13.5.1. Summary Sheet: Reduction and Oxidation Reactions

13.Q. Checkpoint Quiz7 Qns

14. Module 14 (Radicals)

30min

14.1.1. Radical Stability4 min

14.1.2. Example: Radical Stability3 min

14.1.3. Example: Radical Stability1 min

14.1.4. Practice: Radical Stability1 min

14.2.1. Radical Reactions: Radical Halogenation7 min

14.2.2. Radical Reactions: Hydrohalogenation with a Peroxide7 min

14.2.3. Practice: Radical Reactions2 min

14.2.4. Practice: Radical Reactions2 min

14.2.5. Practice: Radical Reactions3 min

14.3.1. Summary Sheet: Radical Reactions

14.Q. Checkpoint Quiz7 Qns

15. Compound Characterization Techniques

1.9hr

15.1.1. Hydrogen Deficiency Index4 min

15.2.1. Infrared Spectroscopy12 min

15.2.2. Example: IR Spectroscopy2 min

15.2.3. Example: IR Spectroscopy52 sec

15.2.4. Practice Question: IR Spectroscopy1 min

15.2.5. Practice Question: IR Spectroscopy 21 min

15.3.1. Mass Spectrometry9 min

15.3.2. Example: Mass Spectrometry4 min

15.3.3. Example: Mass Spectrometry2 min

15.3.4. Example: Mass Spectrometry2 min

15.4.1. UV-vis Spectroscopy5 min

15.4.2. UV-vis Study Sheet

15.5.1. NMR Theory6 min

15.5.2. Example: Intro to NMR2 min

15.5.3. Example: Intro to NMR2 min

15.6.1. Hydrogen (1H NMR)20 min

15.6.2. Example: 1H NMR3 min

15.6.3. Example: 1H NMR6 min

15.6.4. Practice: 1H NMR 3 min

15.6.5. Practice Question: 1H NMR2 min

15.6.6. Practice Question: 1H NMR1 min

15.6.7. Practice Question4 min

15.7.1. Carbon (13C) NMR8 min

15.7.2. Example: 13C NMR3 min

15.7.3. Example: 13C NMR4 min

15.7.4. Practice: 13C NMR3 min

15.7.5. Example: 13C NMR3 min

15.8.1. Structure Elucidation

15.Q. Checkpoint Quiz3 Qns

15.P.1. Practice: Structure Elucidation 1

15.P.2. Practice: Structure Elucidation 2

15.P.3. Practice: Structure Elucidation 3

Mock Exams

ME.1. Term Test 1 - Mock Assessment33 Qns

ME.2. Final Exam - Mock Assessment59 Qns

ME.1 Term Test 1 - Mock Assessment

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