CHEM 353

U of C

Course Overview

Grade Boosters

Lessons & Practice

I. Welcome

1. Review: The Basics (Lewis Structures, Bonding, VSEPR)

1.6hr

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. Bonding in Delocalized Systems3 min

1.5.2. Example: Resonance Structures6 min

1.6.1. VSEPR Theory5 min

1.6.2. Example: VSEPR2 min

1.6.3. Example: VSEPR3 min

1.6.4. Practice: VSEPR4 min

1.7.1. Polar Bonds6 min

1.7.2. Example: Polar Bonds3 min

1.7.3. Example: Polar Bonds 2 min

1.7.4. Practice: Polar Bonds 50 sec

1.8.1. Intermolecular Forces4 min

1.8.2. Melting and Boiling Point Comparison4 min

1.8.3. Example: Intermolecular Forces3 min

1.8.4. Example: Intermolecular Forces2 min

1.8.5. Practice: Intermolecular Forces1 min

1.9.1. Summary Sheet: The Basics

1.Q. Checkpoint Quiz9 Qns

2. Review: Intro to Orgo (Functional Groups, Drawing, Naming)

50min

2.1.1. Summary Sheet: Common Organic Functional Groups

2.1.2. Example: Functional Groups 2 min

2.2.1. Drawing Organic Compouds in 2D2 min

2.2.2. Example: 2-D Notation2 min

2.2.3. Example: 2-D Notation1 min

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

2.2.5. Summary Sheet: Condensed Formula

2.3.1. Drawing Organic Compounds in 3D5 min

2.3.2. Example: 3-D Notation2 min

2.3.3. Example: 3-D Notation2 min

2.3.4. Summary Sheet: Drawing in 3-Dimensions

2.4.1. Chair Conformations4 min

2.4.2. Example: Chair Conformations60 sec

2.4.3. Example: Chair Conformations1 min

2.4.4. Practice: Chair Conformations2 min

2.5.1. IUPAC Systematic Naming Theory15 min

2.5.2. Example: Converting Names to Structures2 min

2.5.3. Example: IUPAC Systematic Naming2 min

2.5.4. Example: IUPAC Systematic Naming2 min

2.5.5. Practice: IUPAC Systematic Naming2 min

2.5.6. Practice: IUPAC Systematic Naming2 min

2.5.7. Summary Sheet: IUPAC Naming

2.Q. Checkpoint Quiz15 Qns

3. Review: Acid/Base Chemistry & Intro to Organic Reactions

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

3.Q. Checkpoint Quiz15 Qns

4. Review: Nucleophilic Substitutions and Elimination Reactions (in the context of alcohols, ethers and epoxides)

1.4hr

4.1.1. General Terminology4 min

4.1.2. Nucleophiles4 min

4.1.3. Electrophiles2 min

4.1.4. Leaving Groups4 min

4.1.5. Substitution vs. Elimination2 min

4.1.6. Example: Substitution vs. Elimination3 min

4.2.1. Molecularity and Rate57 sec

4.2.2. Structural Requirements1 min

4.2.3. SN1 Mechanism4 min

4.2.4. Practice: Sn1 Reaction1 min

4.3.1. Molecularity and Rate1 min

4.3.2. Structural Requirements2 min

4.3.3. SN2 Mechanism4 min

4.3.4. Practice: Sn2 Reaction1 min

4.4.1. Stereochemistry in Substitution Reactions2 min

4.5.1. Leaving Group Ability4 min

4.5.2. Example: Alcohol as a Leaving Group2 min

4.6.1. Solvent Effects in Substitution Reactions6 min

4.7.1. The Williamson Ether Synthesis (*coming soon)

4.7.2. Reactions of Ethers with Strong Acids (*coming soon)

4.8.1. Molecularity and Rate43 sec

4.8.2. Structural Requirements52 sec

4.8.3. E1 Mechanism3 min

4.9.1. Molecularity and Rate45 sec

4.9.2. Structural Requirements2 min

4.9.3. Synthesis of Alkynes1 min

4.9.4. E2 Mechanism3 min

4.10.1. Selectivity in Elimination Reactions - E2 Reactions8 min

4.10.2. Selectivity in Elimination Reactions - E1 Reactions4 min

4.10.3. Example: Selectivity in Elimination Reactions6 min

4.11.1. Favouring Elimination over Subsitution5 min

4.12.1. Summary Sheet: Substitution Reactions

4.12.2. Summary Sheet: Elimination Reactions

4.Q. Checkpoint Quiz13 Qns

4.P.1. Practice: Substitution Question 1

4.P.2. Practice: Substitution Question 2

4.P.3. Practice: Elimination Question 1

4.P.4. Practice: Elimination Question 2

4.P.5. Practice: Elimination Question 3

5. Stereochemistry & Isomers

1.5hr

5.1.1. Summary Sheet: Isomers Flowchart

5.2.1. Constitutional Isomers5 min

5.2.2. Example: Constitutional Isomers4 min

5.2.3. Example: Constitutional Isomers3 min

5.3.1. Conformational Isomers6 min

5.3.2. Example: Conformational Isomers3 min

5.4.1. Geometric or Cis/Trans Isomers6 min

5.4.2. Example: Geometric Isomers4 min

5.4.3. Practice: Geometric Isomers 2 min

5.5.1. Chiral Molecules5 min

5.5.2. Cahn-Ingold-Prelog Rules4 min

5.5.3. Assigning R and S Nomenclature4 min

5.5.4. Example: Stereochemistry7 min

5.5.5. Example: Stereochemistry 24 min

5.5.6. Practice: Stereochemistry 2 min

5.5.7. Practice: Stereochemistry1 min

5.6.1. Optical Isomers13 min

5.6.2. Example: Optical Isomers3 min

5.6.3. Example: Optical Isomers 23 min

5.6.4. Practice: Optical Isomers 1 min

5.7.1. Summary Sheet: IUPAC Naming

5.7.2. Summary Sheet: Naming Molecules with Stereochemistry

5.7.3. Example: Naming Molecules with Stereochemistry4 min

5.7.4. Example: Naming Molecules with Stereochemistry2 min

5.7.5. Practice: Naming Molecules with Stereochemistry2 min

5.8.1. Summary Sheet: Stereochemistry

5.8.2. Summary Sheet: Determining Maximum Number of Stereoisomers

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

5.Q. Checkpoint Quiz10 Qns

6. Electrophilic Addition Reactions to Alkenes/Alkynes

2.3hr

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. Oxymercuration Reactions

6.5.1. Halogenation13 min

6.5.2. Example: Halogenation 13 min

6.5.3. Example: Halogenation 22 min

6.5.4. Example: Halogenation3 min

6.6.1. Ozonolysis9 min

6.6.2. Example: Ozonolysis 12 min

6.6.3. Example: Ozonolysis4 min

6.7.1. Dihydroxylation5 min

6.7.2. Example: Dihydroxylation3 min

6.8.1. Epoxidation8 min

6.8.2. Example: Epoxidation3 min

6.8.3. Example: Epoxides as Electrophiles8 min

6.9.1. Hydrogenation6 min

6.9.2. Example: Hydrogenation 13 min

6.9.3. Example: Hydrogenation 22 min

6.9.4. Example: Hydrogenation 31 min

6.9.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

6.10.1. Carbocation Rearrangements6 min

6.10.2. Example: Carbocation Rearrangements3 min

6.10.3. Example: Carbocation Rearrangements3 min

6.11.1. Reactivity of Dienes (*coming soon)

6.11.2. 1,2- and 1,4-addition of HX to dienes (*coming soon)

6.12.1. Terpene Biosynthesis2 min

6.12.2. Example: Terpene Biosynthesis 12 min

6.12.3. Example: Terpene Biosynthesis4 min

6.13.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

6.Q. Checkpoint Quiz9 Qns

6.P.1. Practice: Reaction Energy Diagrams

7. Conjugated Systems

1.6hr

7.I. Conjugated Systems Intro32 sec

7.1.1. Conjugated Systems & Radical Reactions16 min

7.1.2. Addition Reactions on Conjugated Systems7 min

7.2.1. Mechanism and Orbital Description of Diels-Alder Reaction23 min

7.2.2. Stereochemistry of Diels-Alder Reaction10 min

7.2.3. Example: Diels-Alder Reaction12 min

7.2.4. Practice: Diels-Alder Reaction18 min

7.2.5. Practice: Diels-Alder Reaction9 min

7.Q. Quiz: Diels-Alder Reaction3 Qns

8. Radical Reactions

30min

8.1.1. Radical Stability4 min

8.1.2. Example: Radical Stability3 min

8.1.3. Example: Radical Stability1 min

8.1.4. Practice: Radical Stability1 min

8.2.1. Radical Reactions: Radical Halogenation7 min

8.2.2. Radical Reactions: Hydrohalogenation with a Peroxide7 min

8.2.3. Practice: Radical Reactions2 min

8.2.4. Practice: Radical Reactions2 min

8.2.5. Practice: Radical Reactions3 min

8.3.1. Summary Sheet: Radical Reactions

8.Q. Checkpoint Quiz7 Qns

9. Alcohols, Ethers and Epoxides

1.2hr

9.I. Chapter Intro

9.1.1. Acid-catalyzed Hydration9 min

9.1.2. Example: Acid-catalyzed Hydration4 min

9.1.3. Example: Acid-catalyzed Hydration 23 min

9.2.1. Hydroboration/Oxidation8 min

9.2.2. Example: Hydroboration 13 min

9.2.3. Example: Hydroboration 22 min

9.3.1. Dihydroxylation5 min

9.3.2. Example: Dihydroxylation3 min

9.4.1. Leaving Group Ability4 min

9.4.2. Example: Alcohol as a Leaving Group2 min

9.5.1. Epoxidation8 min

9.5.2. Example: Epoxidation3 min

9.5.3. Example: Epoxides as Electrophiles8 min

9.6.1. Williamson Ether Synthesis8 min

10. Reduction and Oxidation Reactions

42min

10.1.1. Structure and Reactivity (*coming soon)

10.2.1. Thiols (*coming soon)

10.2.2. Sulfides (*coming soon)

10.3.1. Oxidation to make Aldehydes4 min

10.3.2. Oxidation to make Ketones2 min

10.3.3. Oxidation of Aldehydes3 min

10.3.4. Example: Oxidation Reactions5 min

10.4.1. Reduction using NaBH42 min

10.4.2. Reduction using LiAlH44 min

10.4.3. Example: Reduction Reactions3 min

10.4.4. Example: Reductions Reactions5 min

10.5.1. Hydrogenation6 min

10.5.2. Example: Hydrogenation3 min

10.5.3. Example: Hydrogenation2 min

10.5.4. Example: Hydrogenation1 min

10.5.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

10.6.1. Summary Sheet: Reduction and Oxidation Reactions

10.Q. Checkpoint Quiz7 Qns

11. Aromatic Systems

48min

11.1.1. Aromaticity13 min

11.1.2. Summary Sheet: Naming Aromatic Rings

11.1.3. Example: Aromaticity5 min

11.1.4. Example: Aromaticity3 min

11.1.5. Practice: Aromaticity2 min

11.3.1. Electrophilic Aromatic Substitution Reactions 8 min

11.3.2. Electrophilic Aromatic Substitution4 min

11.4.1. Considerations for Electrophilic Aromatic Substitutions6 min

11.4.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

11.4.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

11.5.1. Summary Sheet: Aromaticity and Related Reactions

11.5.2. Summary Sheet: Naming Aromatic Rings

11.Q. Checkpoint Quiz4 Qns

12. Aldehydes and Ketones (Addition to Carbonyls/Reactivity of Enolates)

1.9hr

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.Q. Checkpoint Quiz4 Qns

13. Carboxylic Acid Derivatives (Nucleophilic Acyl Substitutions)

1.1hr

13.1.1. Carboxylic Acids2 min

13.1.2. Example: Carboxylic Acids5 min

13.1.3. Example: Carboxylic Acids2 min

13.2.1. Nomenclature and Physical Properties3 min

13.3.1. General Reactivity3 min

13.3.2. General Mechanism at the Carbonyl2 min

13.3.3. Practice: General Reactivity34 sec

13.3.4. Summary Sheet: Carboxylic Acid Reactivity

13.4.1. Acyl Halides3 min

13.4.2. Example: Acyl Halides2 min

13.4.3. Example: Acyl Halides 22 min

13.5.1. Synthesis of Anhydrides

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

13.5.3. Other Syntheses of Esters1 min

13.5.4. Transesterification2 min

13.5.5. Example: Esters and Anhydrides9 min

13.5.6. Example: Esters and Anhydrides 28 min

13.6.1. Formation of Amides from Acid Halides1 min

13.6.2. Example: Amides3 min

13.6.3. Example: Amides2 min

13.6.4. Practice: Peptide Bonds50 sec

13.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

13.7.2. Hydrolysis of Esters and Amides24 sec

13.8.1. Claisen Reactions3 min

13.8.2. Example: Claisen Reactions4 min

13.8.3. Example: Claisen Reactions2 min

13.8.4. Example: Dieckmann Condensation3 min

13.9.1. Nucleophilic Acyl Substitutions

13.Q. Checkpoint Quiz13 Qns

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