CHEM 2OD3

Mac

Course Overview

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: Stereochemistry & Isomers

1.5hr

2.1.1. Summary Sheet: Isomers Flowchart

2.2.1. Constitutional Isomers5 min

2.2.2. Example: Constitutional Isomers4 min

2.2.3. Example: Constitutional Isomers3 min

2.3.1. Conformational Isomers6 min

2.3.2. Example: Conformational Isomers3 min

2.4.1. Geometric or Cis/Trans Isomers6 min

2.4.2. Example: Geometric Isomers4 min

2.4.3. Practice: Geometric Isomers 2 min

2.5.1. Chiral Molecules5 min

2.5.2. Cahn-Ingold-Prelog Rules4 min

2.5.3. Assigning R and S Nomenclature4 min

2.5.4. Example: Stereochemistry7 min

2.5.5. Example: Stereochemistry 24 min

2.5.6. Practice: Stereochemistry 2 min

2.5.7. Practice: Stereochemistry1 min

2.6.1. Optical Isomers13 min

2.6.2. Example: Optical Isomers3 min

2.6.3. Example: Optical Isomers 23 min

2.6.4. Practice: Optical Isomers 1 min

2.7.1. Summary Sheet: IUPAC Naming

2.7.2. Summary Sheet: Naming Molecules with Stereochemistry

2.7.3. Example: Naming Molecules with Stereochemistry4 min

2.7.4. Example: Naming Molecules with Stereochemistry2 min

2.7.5. Practice: Naming Molecules with Stereochemistry2 min

2.8.1. Summary Sheet: Stereochemistry

2.8.2. Summary Sheet: Determining Maximum Number of Stereoisomers

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

2.Q. Checkpoint Quiz10 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. Radical Reactions

30min

4.1.1. Radical Stability4 min

4.1.2. Example: Radical Stability3 min

4.1.3. Example: Radical Stability1 min

4.1.4. Practice: Radical Stability1 min

4.2.1. Radical Reactions: Radical Halogenation7 min

4.2.2. Radical Reactions: Hydrohalogenation with a Peroxide7 min

4.2.3. Practice: Radical Reactions2 min

4.2.4. Practice: Radical Reactions2 min

4.2.5. Practice: Radical Reactions3 min

4.3.1. Summary Sheet: Radical Reactions

4.Q. Checkpoint Quiz7 Qns

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

50min

5.1.1. Summary Sheet: Common Organic Functional Groups

5.1.2. Example: Functional Groups 2 min

5.2.1. Drawing Organic Compouds in 2D2 min

5.2.2. Example: 2-D Notation2 min

5.2.3. Example: 2-D Notation1 min

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

5.2.5. Summary Sheet: Condensed Formula

5.3.1. Drawing Organic Compounds in 3D5 min

5.3.2. Example: 3-D Notation2 min

5.3.3. Example: 3-D Notation2 min

5.3.4. Summary Sheet: Drawing in 3-Dimensions

5.4.1. Chair Conformations4 min

5.4.2. Example: Chair Conformations60 sec

5.4.3. Example: Chair Conformations1 min

5.4.4. Practice: Chair Conformations2 min

5.5.1. IUPAC Systematic Naming Theory15 min

5.5.2. Example: Converting Names to Structures2 min

5.5.3. Example: IUPAC Systematic Naming2 min

5.5.4. Example: IUPAC Systematic Naming2 min

5.5.5. Practice: IUPAC Systematic Naming2 min

5.5.6. Practice: IUPAC Systematic Naming2 min

5.5.7. Summary Sheet: IUPAC Naming

5.Q. Checkpoint Quiz15 Qns

6. Alcohols and Ethers

1.2hr

6.I. Chapter Intro

6.1.1. Acid-catalyzed Hydration9 min

6.1.2. Example: Acid-catalyzed Hydration4 min

6.1.3. Example: Acid-catalyzed Hydration 23 min

6.2.1. Hydroboration/Oxidation8 min

6.2.2. Example: Hydroboration 13 min

6.2.3. Example: Hydroboration 22 min

6.3.1. Dihydroxylation5 min

6.3.2. Example: Dihydroxylation3 min

6.4.1. Leaving Group Ability4 min

6.4.2. Example: Alcohol as a Leaving Group2 min

6.5.1. Epoxidation8 min

6.5.2. Example: Epoxidation3 min

6.5.3. Example: Epoxides as Electrophiles8 min

6.6.1. Williamson Ether Synthesis8 min

7. Reduction and Oxidation Reactions

42min

7.1.1. Structure and Reactivity (*coming soon)

7.2.1. Thiols (*coming soon)

7.2.2. Sulfides (*coming soon)

7.3.1. Oxidation to make Aldehydes4 min

7.3.2. Oxidation to make Ketones2 min

7.3.3. Oxidation of Aldehydes3 min

7.3.4. Example: Oxidation Reactions5 min

7.4.1. Reduction using NaBH42 min

7.4.2. Reduction using LiAlH44 min

7.4.3. Example: Reduction Reactions3 min

7.4.4. Example: Reductions Reactions5 min

7.5.1. Hydrogenation6 min

7.5.2. Example: Hydrogenation3 min

7.5.3. Example: Hydrogenation2 min

7.5.4. Example: Hydrogenation1 min

7.5.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

7.6.1. Summary Sheet: Reduction and Oxidation Reactions

7.Q. Checkpoint Quiz7 Qns

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

1.4hr

8.1.1. General Terminology4 min

8.1.2. Nucleophiles4 min

8.1.3. Electrophiles2 min

8.1.4. Leaving Groups4 min

8.1.5. Substitution vs. Elimination2 min

8.1.6. Example: Substitution vs. Elimination3 min

8.2.1. Molecularity and Rate57 sec

8.2.2. Structural Requirements1 min

8.2.3. SN1 Mechanism4 min

8.2.4. Practice: Sn1 Reaction1 min

8.3.1. Molecularity and Rate1 min

8.3.2. Structural Requirements2 min

8.3.3. SN2 Mechanism4 min

8.3.4. Practice: Sn2 Reaction1 min

8.4.1. Stereochemistry in Substitution Reactions2 min

8.5.1. Leaving Group Ability4 min

8.5.2. Example: Alcohol as a Leaving Group2 min

8.6.1. Solvent Effects in Substitution Reactions6 min

8.7.1. The Williamson Ether Synthesis (*coming soon)

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

8.8.1. Molecularity and Rate43 sec

8.8.2. Structural Requirements52 sec

8.8.3. E1 Mechanism3 min

8.9.1. Molecularity and Rate45 sec

8.9.2. Structural Requirements2 min

8.9.3. Synthesis of Alkynes1 min

8.9.4. E2 Mechanism3 min

8.10.1. Selectivity in Elimination Reactions - E2 Reactions8 min

8.10.2. Selectivity in Elimination Reactions - E1 Reactions4 min

8.10.3. Example: Selectivity in Elimination Reactions6 min

8.11.1. Favouring Elimination over Subsitution5 min

8.12.1. Summary Sheet: Substitution Reactions

8.12.2. Summary Sheet: Elimination Reactions

8.Q. Checkpoint Quiz13 Qns

8.P.1. Practice: Substitution Question 1

8.P.2. Practice: Substitution Question 2

8.P.3. Practice: Elimination Question 1

8.P.4. Practice: Elimination Question 2

8.P.5. Practice: Elimination Question 3

9. Structure Elucidation (IR Spectroscopy, NMR, Mass Spectrometry)

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. UV-vis Spectroscopy5 min

9.4.2. UV-vis Study Sheet

9.5.1. NMR Theory6 min

9.5.2. Example: Intro to NMR2 min

9.5.3. Example: Intro to NMR2 min

9.6.1. Hydrogen (1H NMR)20 min

9.6.2. Example: 1H NMR3 min

9.6.3. Example: 1H NMR6 min

9.6.4. Practice: 1H NMR 3 min

9.6.5. Practice Question: 1H NMR2 min

9.6.6. Practice Question: 1H NMR1 min

9.6.7. Practice Question4 min

9.7.1. Carbon (13C) NMR8 min

9.7.2. Example: 13C NMR3 min

9.7.3. Example: 13C NMR4 min

9.7.4. Practice: 13C NMR3 min

9.7.5. Example: 13C NMR3 min

9.8.1. Structure Elucidation

9.Q. Checkpoint Quiz3 Qns

9.P.1. Practice: Structure Elucidation 1

9.P.2. Practice: Structure Elucidation 2

9.P.3. Practice: Structure Elucidation 3

10. Conjugated Systems

1.6hr

10.I. Conjugated Systems Intro32 sec

10.1.1. Conjugated Systems & Radical Reactions16 min

10.1.2. Addition Reactions on Conjugated Systems7 min

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

10.2.2. Stereochemistry of Diels-Alder Reaction10 min

10.2.3. Example: Diels-Alder Reaction12 min

10.2.4. Practice: Diels-Alder Reaction18 min

10.2.5. Practice: Diels-Alder Reaction9 min

10.Q. Quiz: Diels-Alder Reaction3 Qns

11. Electrophilic Addition Reactions to Alkenes/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. Aromatic Compounds

48min

12.1.1. Aromaticity13 min

12.1.2. Summary Sheet: Naming Aromatic Rings

12.1.3. Example: Aromaticity5 min

12.1.4. Example: Aromaticity3 min

12.1.5. Practice: Aromaticity2 min

12.3.1. Electrophilic Aromatic Substitution Reactions 8 min

12.3.2. Electrophilic Aromatic Substitution4 min

12.4.1. Considerations for Electrophilic Aromatic Substitutions6 min

12.4.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

12.4.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

12.5.1. Summary Sheet: Aromaticity and Related Reactions

12.5.2. Summary Sheet: Naming Aromatic Rings

12.Q. Checkpoint Quiz4 Qns

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

1.9hr

13.1.1. Nomenclature and Physical Properties3 min

13.2.1. General Reactivity1 min

13.2.2. General Mechanism at the Carbonyl4 min

13.3.1. The Grignard Reaction5 min

13.3.2. Cyanohydrin Formation3 min

13.3.3. Example: The Grignard Reaction2 min

13.3.4. Practice: The Grignard Reaction5 min

13.4.1. General Reactions with Oxygen Nucleophiles5 min

13.4.2. Hydrate Formation1 min

13.4.3. Acetal Formation2 min

13.4.4. Ketal Formation2 min

13.4.5. Hydrolysis of Acetals and Ketals3 min

13.4.6. General Mechanism with Oxygen Nucleophiles9 min

13.4.7. Stability of Hemiketals and Hemiacetals3 min

13.4.8. Practice: Ketals and Acetals as Protecting Groups2 min

13.4.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

13.4.11. Practice: Mechanism in Acetal and Ketal Formation3 min

13.4.12. Practice: Identifying Acetals/Aldehydes2 min

13.5.1. Synthesis and Hydrolysis of Imines7 min

13.5.2. Enamine Formation2 min

13.5.3. Mechanism of Imiine Formation4 min

13.5.4. Reductive Amination2 min

13.5.5. Practice: Imine Formation2 min

13.6.1. Tautomerization8 min

13.6.2. Enolate Formation3 min

13.6.3. Kinetic vs. Thermodynamic Enolates5 min

13.6.4. The Aldol Reaction3 min

13.6.5. Mechanism of the Aldol Reaction5 min

13.6.6. The Retro-Aldol Reaction1 min

13.6.7. Mixed Aldol Reactions5 min

13.6.8. Example: The Aldol Reaction4 min

13.6.9. Practice: The Aldol Reaction2 min

13.7.1. Study Sheet: Reaction Overview and Key Ideas

13.Q. Checkpoint Quiz4 Qns

14. Carboxylic Acid Derivatives (Nucleophilic Acyl Substitutions)

1.1hr

14.1.1. Carboxylic Acids2 min

14.1.2. Example: Carboxylic Acids5 min

14.1.3. Example: Carboxylic Acids2 min

14.2.1. Nomenclature and Physical Properties3 min

14.3.1. General Reactivity3 min

14.3.2. General Mechanism at the Carbonyl2 min

14.3.3. Practice: General Reactivity34 sec

14.3.4. Summary Sheet: Carboxylic Acid Reactivity

14.4.1. Acyl Halides3 min

14.4.2. Example: Acyl Halides2 min

14.4.3. Example: Acyl Halides 22 min

14.5.1. Synthesis of Anhydrides

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

14.5.3. Other Syntheses of Esters1 min

14.5.4. Transesterification2 min

14.5.5. Example: Esters and Anhydrides9 min

14.5.6. Example: Esters and Anhydrides 28 min

14.6.1. Formation of Amides from Acid Halides1 min

14.6.2. Example: Amides3 min

14.6.3. Example: Amides2 min

14.6.4. Practice: Peptide Bonds50 sec

14.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

14.7.2. Hydrolysis of Esters and Amides24 sec

14.8.1. Claisen Reactions3 min

14.8.2. Example: Claisen Reactions4 min

14.8.3. Example: Claisen Reactions2 min

14.8.4. Example: Dieckmann Condensation3 min

14.9.1. Nucleophilic Acyl Substitutions

14.Q. Checkpoint Quiz13 Qns

15. Amines

17min

15.I. Chapter Intro

15.1.1. Synthesis and Hydrolysis of Imines7 min

15.1.2. Enamine Formation2 min

15.1.3. Mechanism of Imiine Formation4 min

15.1.4. Reductive Amination2 min

15.1.5. Practice: Imine Formation2 min

16. Carbohydrates

56min

16.1.1. Straight Chain Nomenclature7 min

16.1.2. Cyclization of Monosaccharides5 min

16.1.3. Cyclic Nomenclature6 min

16.1.4. Glycosidic Bonds2 min

16.1.5. Example: Carbohydrate Nomenclature3 min

16.1.6. Example: Carbohydrate Nomenclature (Glycosides)4 min

16.2.1. Converting Fischer Structures4 min

16.2.2. Example: Converting Fischer Structures3 min

16.2.3. Example: Converting Fischer Structures3 min

16.2.4. Practice Question: Converting Fischer Projections2 min

16.3.1. Carbohydrate Reactions: Formation of Glycosidic Bonds4 min

16.3.2. Carbohydrate Reactions: Hydrolysis of Glycosidic Bonds1 min

16.3.3. Carbohydrate Reactions: Reducing Sugars2 min

16.3.4. Practice: Carbohydrates in Solution1 min

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

16.3.6. Example: Identifying Reducing Sugars2 min

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

16.4.1. Carbohydrates

16.Q. Checkpoint Quiz15 Qns

17. Organic Chemistry of Other Biological Molecules (*coming soon)

17.1.1. Structure of Amino Acids (*coming soon)

17.1.2. pKa of Amino Acids (*coming soon)

17.1.3. pH, pKa, and titrations with amino acids (*coming soon)

17.2.1. Lipids (*coming soon)

17.2.2. Sterols (*coming soon)

Mock Exams

ME.1. Term Exam 1- Exam-like Practice Problem Set49 Qns

ME.2. Final Exam - Mock Assessment110 Qns

ME.2 Final Exam - Mock Assessment

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