CHEM 233

UBC

Course Overview

Grade Boosters

Lessons & Practice

1. Course Introduction & Intermolecular Forces

1.1hr

1.1.1. Drawing Organic Compouds in 2D2 min

1.1.2. Example: 2-D Notation2 min

1.1.3. Example: 2-D Notation1 min

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

1.1.5. Summary Sheet: Condensed Formula

1.2.1. Drawing Organic Compounds in 3D5 min

1.2.2. Example: 3-D Notation2 min

1.2.3. Example: 3-D Notation2 min

1.2.4. Summary Sheet: Drawing in 3-Dimensions

1.3.1. Polar Bonds and Electronegativity6 min

1.3.2. Example: Polar Bonds3 min

1.3.3. Example: Polar Bonds 2 min

1.3.4. Practice: Polar Bonds 50 sec

1.4.1. Intermolecular Forces4 min

1.4.2. Melting and Boiling Point Comparison4 min

1.4.3. Example: Intermolecular Forces3 min

1.4.4. Example: Intermolecular Forces2 min

1.4.5. Practice: Intermolecular Forces1 min

1.4.6. Summary Sheet: Intermolecular Forces

1.5.1. Summary Sheet: Common Organic Functional Groups

1.5.2. Example: Functional Groups 2 min

1.6.1. IUPAC Systematic Naming Theory15 min

1.6.2. Example: Converting Names to Structures2 min

1.6.3. Example: IUPAC Systematic Naming2 min

1.6.4. Example: IUPAC Systematic Naming2 min

1.6.5. Practice: IUPAC Systematic Naming2 min

1.6.6. Practice: IUPAC Systematic Naming2 min

1.6.7. Summary Sheet: IUPAC Naming

2. Bonding & Resonance

1.9hr

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. Bonding Models

2.3.1. Valence Bond Theory and Hybridization7 min

2.3.2. Example: Valence Bond Theory/Hybridization5 min

2.3.3. Practice: Valence Bond Theory/Hybridization

2.3.4. Further Example: Valence Bond Theory and Hybridization2 min

2.3.5. Sigma and Pi Bonds1 min

2.3.6. Valence Bond Theory, Hybridization, and MO Theory: Another Explanation

2.4.1. Molecular Orbital Theory4 min

2.5.1. VSEPR Theory5 min

2.5.2. Example: VSEPR2 min

2.5.3. Example: VSEPR3 min

2.5.4. Practice: VSEPR4 min

2.6.1. Bonding in Delocalized Systems3 min

2.6.2. Example: Resonance Structures6 min

2.6.3. Equivalent Resonance Structures6 min

2.6.4. Non-equivalent Resonance Structures3 min

2.6.5. Valence Bond Theory, Hybridization, MO Theory

2.6.6. Drawing Resonance Structures

2.6.7. Resonance Structures: Stability

2.6.8. Resonance Arrow Pushing

2.6.9. Invoking Resonance Structures

2.6.10. Lewis Structures: Resonance

2.6.11. Lewis Structures: Resonance Additional Practice

2.6.12. Lewis Structures: Resonance Additional Practice

2.6.13. Resonance Theory7 min

2.7.1. Summary Sheet: Bonding and Resonance

2.8.1. Aromaticity13 min

2.8.2. Summary Sheet: Naming Aromatic Rings

2.8.3. Example: Aromaticity5 min

2.8.4. Example: Aromaticity3 min

2.8.5. Practice: Aromaticity2 min

3. Acids & Bases & Stereochemistry

2.4hr

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. Important pKas You Should Know4 min

3.2.2. Relationship Between pH and pKa2 min

3.2.3. Amino Acids at Different pHs3 min

3.2.4. Practice: Amino Acids in Solution3 min

3.2.5. Practice: Amino Acids in Solution3 min

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

3.2.7. Summary Sheet: pKa's of Common Molecules

3.3.1. Factors Influencing Acid/Base Strength2 min

3.3.2. Electronegativity1 min

3.3.3. Atom Size2 min

3.3.4. Resonance3 min

3.3.5. Hybridization3 min

3.3.6. Induction3 min

3.3.7. Aromaticity3 min

3.3.8. Example: Acid/Base Strength 3 min

3.3.9. Example: Acid/Base Strength 3 min

3.3.10. Practice: Acid/Base Equilibria 2 min

3.3.11. Practice: Acid/Base Equilibria 2 min

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

3.5.1. Summary Sheet: Isomers Flowchart

3.6.1. Constitutional Isomers5 min

3.6.2. Example: Constitutional Isomers4 min

3.6.3. Example: Constitutional Isomers3 min

3.7.1. Conformational Isomers6 min

3.7.2. Example: Conformational Isomers3 min

3.8.1. Geometric or Cis/Trans Isomers6 min

3.8.2. Example: Geometric Isomers4 min

3.8.3. Practice: Geometric Isomers 2 min

3.9.1. Chiral Molecules5 min

3.9.2. Cahn-Ingold-Prelog Rules4 min

3.9.3. Assigning R and S Nomenclature4 min

3.9.4. Example: Stereochemistry7 min

3.9.5. Example: Stereochemistry 24 min

3.9.6. Practice: Stereochemistry 2 min

3.9.7. Practice: Stereochemistry1 min

3.10.1. Optical Isomers13 min

3.10.2. Example: Optical Isomers3 min

3.10.3. Example: Optical Isomers 23 min

3.10.4. Practice: Optical Isomers 1 min

3.11.1. Summary Sheet: IUPAC Naming

3.11.2. Summary Sheet: Naming Molecules with Stereochemistry

3.11.3. Example: Naming Molecules with Stereochemistry4 min

3.11.4. Example: Naming Molecules with Stereochemistry2 min

3.11.5. Practice: Naming Molecules with Stereochemistry2 min

3.12.1. Summary Sheet: Stereochemistry

3.12.2. Summary Sheet: Determining Maximum Number of Stereoisomers

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

4. Electrophilic Addition to Alkenes

2.2hr

4.1.1. Hydrohalogenation9 min

4.1.2. Example: Hydrohalogenation4 min

4.1.3. Example: Hydrohalogenation4 min

4.2.1. Acid-catalyzed Hydration9 min

4.2.2. Example: Acid-catalyzed Hydration4 min

4.2.3. Example: Acid-catalyzed Hydration 23 min

4.3.1. Carbocation Rearrangements6 min

4.3.2. Example: Carbocation Rearrangements3 min

4.3.3. Example: Carbocation Rearrangements3 min

4.4.1. Hydroboration/Oxidation8 min

4.4.2. Example: Hydroboration 13 min

4.4.3. Example: Hydroboration 22 min

4.5.1. Halogenation13 min

4.5.2. Example: Halogenation 13 min

4.5.3. Example: Halogenation 22 min

4.5.4. Example: Halogenation3 min

4.6.1. Ozonolysis9 min

4.6.2. Example: Ozonolysis 12 min

4.6.3. Example: Ozonolysis4 min

4.7.1. Dihydroxylation5 min

4.7.2. Example: Dihydroxylation3 min

4.8.1. Epoxidation8 min

4.8.2. Example: Epoxidation3 min

4.8.3. Example: Epoxides as Electrophiles8 min

4.9.1. Hydrogenation6 min

4.9.2. Example: Hydrogenation 13 min

4.9.3. Example: Hydrogenation 22 min

4.9.4. Example: Hydrogenation 31 min

4.9.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

4.10.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

4.11.1. Preparation of Alkynes from Vicinal Dihalides

4.11.2. Preparation of Alkynes from Geminal Dihalides

4.11.3. C-C Bond Formation Using Terminal Alkynes

4.12.1. Hydrogenation of Alkynes (Review)

4.12.2. Hydrohalogenation of Alkynes

4.12.3. Hydrohalogenation of Alkynes with HBr and Peroxides

4.12.4. Mercury-Catalyzed Hydration of Alkynes

4.12.5. Hydroboration-Oxidation of Alkynes

4.12.6. Halogenation of Alkynes

4.12.7. Ozonolysis of Alkynes

5. Unimolecular Mechanisms (SN1 and E1) & Terpene Biosynthesis

49min

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. SN1 Reactions Theory: Carbocation Stability

5.2.2. Carbocation Stability

5.3.1. Molecularity and Rate57 sec

5.3.2. Structural Requirements1 min

5.3.3. SN1 Mechanism4 min

5.3.4. Practice: Sn1 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 Reactions

5.7.1. Molecularity and Rate43 sec

5.7.2. Structural Requirements52 sec

5.7.3. E1 Mechanism3 min

5.8.1. Selectivity in Elimination Reactions - E1 Reactions4 min

5.9.1. Favouring Elimination over Subsitution

5.10.1. Summary Sheet: Substitution Reactions

5.10.2. Summary Sheet: Elimination Reactions

5.11.1. Terpene Biosynthesis2 min

5.11.2. Example: Terpene Biosynthesis 12 min

5.11.3. Example: Terpene Biosynthesis4 min

5.P.1. Practice: Substitution Question 1

6. Bimolecular Mechanisms (SN2 and E2)

1.4hr

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. Molecularity and Rate1 min

6.3.2. Structural Requirements2 min

6.3.3. SN2 Mechanism4 min

6.3.4. Practice: Sn2 Reaction1 min

6.4.1. Stereochemistry in Substitution Reactions2 min

6.5.1. Leaving Group Ability4 min

6.5.2. Example: Alcohol as a Leaving Group2 min

6.6.1. Solvent Effects in Substitution Reactions6 min

6.7.1. Molecularity and Rate43 sec

6.7.2. Structural Requirements52 sec

6.7.3. E1 Mechanism3 min

6.8.1. Molecularity and Rate45 sec

6.8.2. Structural Requirements2 min

6.8.3. Synthesis of Alkynes1 min

6.8.4. E2 Mechanism3 min

6.9.1. Selectivity in Elimination Reactions - E2 Reactions8 min

6.9.2. Selectivity in Elimination Reactions - E1 Reactions4 min

6.9.3. Example: Selectivity in Elimination Reactions6 min

6.10.1. Favouring Elimination over Subsitution5 min

6.11.1. Summary Sheet: Substitution Reactions

6.11.2. Summary Sheet: Elimination Reactions

6.P.1. Practice: Substitution Question 1

6.P.2. Practice: Substitution Question 2

6.P.3. Practice: Elimination Question 1

6.P.4. Practice: Elimination Question 2

6.P.5. Practice: Elimination Question 3

7. Addition to Carbonyls (Aldehydes and Ketones)

1.3hr

7.1.1. Nomenclature and Physical Properties3 min

7.2.1. General Reactivity1 min

7.2.2. General Mechanism at the Carbonyl4 min

7.3.1. The Grignard Reaction5 min

7.3.2. Cyanohydrin Formation3 min

7.3.3. Example: The Grignard Reaction2 min

7.3.4. Practice: The Grignard Reaction5 min

7.4.1. General Reactions with Oxygen Nucleophiles5 min

7.4.2. Hydrate Formation1 min

7.4.3. Acetal Formation2 min

7.4.4. Ketal Formation2 min

7.4.5. Hydrolysis of Acetals and Ketals3 min

7.4.6. General Mechanism with Oxygen Nucleophiles9 min

7.4.7. Stability of Hemiketals and Hemiacetals3 min

7.4.8. Practice: Ketals and Acetals as Protecting Groups2 min

7.4.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

7.4.11. Practice: Mechanism in Acetal and Ketal Formation3 min

7.4.12. Practice: Identifying Acetals/Aldehydes2 min

7.5.1. Synthesis and Hydrolysis of Imines7 min

7.5.2. Enamine Formation2 min

7.5.3. Mechanism of Imiine Formation4 min

7.5.4. Reductive Amination2 min

7.5.5. Practice: Imine Formation2 min

7.6.1. Study Sheet: Reaction Overview and Key Ideas

8. Carbohydrates

56min

8.1.1. Straight Chain Nomenclature7 min

8.1.2. Cyclization of Monosaccharides5 min

8.1.3. Cyclic Nomenclature6 min

8.1.4. Glycosidic Bonds2 min

8.1.5. Example: Carbohydrate Nomenclature3 min

8.1.6. Example: Carbohydrate Nomenclature (Glycosides)4 min

8.2.1. Converting Fischer Structures4 min

8.2.2. Example: Converting Fischer Structures3 min

8.2.3. Example: Converting Fischer Structures3 min

8.2.4. Practice Question: Converting Fischer Projections2 min

8.3.1. Carbohydrate Reactions: Formation of Glycosidic Bonds4 min

8.3.2. Carbohydrate Reactions: Hydrolysis of Glycosidic Bonds1 min

8.3.3. Carbohydrate Reactions: Reducing Sugars2 min

8.3.4. Practice: Carbohydrates in Solution1 min

8.3.5. Example: Tollen's Reagent and Reducing Sugars1 min

8.3.6. Example: Identifying Reducing Sugars2 min

8.3.7. Example: Ketoses with the Tollen's Test3 min

8.4.1. Carbohydrates

9. Nucleophilic Acyl Substitutions (Carboxylic Acid Derivatives)

53min

9.1.1. Carboxylic Acids2 min

9.1.2. Example: Carboxylic Acids5 min

9.1.3. Example: Carboxylic Acids2 min

9.2.1. Nomenclature and Physical Properties3 min

9.3.1. General Reactivity3 min

9.3.2. General Mechanism at the Carbonyl2 min

9.3.3. Practice: General Reactivity34 sec

9.3.4. Summary Sheet: Carboxylic Acid Reactivity

9.4.1. Acyl Halides3 min

9.4.2. Example: Acyl Halides2 min

9.4.3. Example: Acyl Halides 22 min

9.5.1. Synthesis of Anhydrides

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

9.5.3. Other Syntheses of Esters1 min

9.5.4. Transesterification2 min

9.5.5. Example: Esters and Anhydrides9 min

9.5.6. Example: Esters and Anhydrides 28 min

9.6.1. Formation of Amides from Acid Halides1 min

9.6.2. Example: Amides3 min

9.6.3. Example: Amides2 min

9.6.4. Practice: Peptide Bonds50 sec

9.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

9.7.2. Hydrolysis of Esters and Amides24 sec

9.8.1. Nucleophilic Acyl Substitutions

10. Oxidation and Reduction

42min

10.1.1. Oxidation to make Aldehydes4 min

10.1.2. Oxidation to make Ketones2 min

10.1.3. Oxidation of Aldehydes3 min

10.1.4. Example: Oxidation Reactions5 min

10.2.1. Reduction using NaBH42 min

10.2.2. Reduction using LiAlH44 min

10.2.3. Example: Reduction Reactions3 min

10.2.4. Example: Reductions 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

11. Enolate Chemistry (Aldol and Claisen)

47min

11.1.1. Tautomerization8 min

11.1.2. Enolate Formation3 min

11.1.3. Kinetic vs. Thermodynamic Enolates5 min

11.1.4. The Aldol Reaction3 min

11.1.5. Mechanism of the Aldol Reaction5 min

11.1.6. The Retro-Aldol Reaction1 min

11.1.7. Mixed Aldol Reactions5 min

11.1.8. Example: The Aldol Reaction4 min

11.1.9. Practice: The Aldol Reaction2 min

11.2.1. Claisen Reactions3 min

11.2.2. Example: Claisen Reactions4 min

11.2.3. Example: Claisen Reactions2 min

11.2.4. Example: Dieckmann Condensation3 min

11.3.1. Chapter 11. Reactions of Enolates

11.3.2. Nucleophilic Acyl Substitutions vs. Claisen Reaction

11.P.1. Carbonyl Practice Question 1

11.P.2. Carbonyl Practice Question 2

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