CHEM 222

McGill

Course Overview

Lessons & Practice

I. Welcome

1. Core Topic 1 & 2: NMR Spectroscopy & Structure Determination

1.9hr

1.1.1. Hydrogen Deficiency Index4 min

1.2.1. Infrared Spectroscopy12 min

1.2.2. Example: IR Spectroscopy2 min

1.2.3. Example: IR Spectroscopy52 sec

1.2.4. Practice Question: IR Spectroscopy1 min

1.2.5. Practice Question: IR Spectroscopy 21 min

1.3.1. Mass Spectrometry9 min

1.3.2. Example: Mass Spectrometry4 min

1.3.3. Example: Mass Spectrometry2 min

1.3.4. Example: Mass Spectrometry2 min

1.4.1. NMR Theory6 min

1.4.2. Example: Intro to NMR2 min

1.4.3. Example: Intro to NMR2 min

1.5.1. Hydrogen (1H NMR)20 min

1.5.2. Example: 1H NMR3 min

1.5.3. Example: 1H NMR6 min

1.5.4. Practice: 1H NMR 3 min

1.5.5. Practice Question: 1H NMR2 min

1.5.6. Practice Question: 1H NMR1 min

1.5.7. Practice Question4 min

1.6.1. Carbon (13C) NMR8 min

1.6.2. Example: 13C NMR3 min

1.6.3. Example: 13C NMR4 min

1.6.4. Practice: 13C NMR3 min

1.6.5. Example: 13C NMR3 min

1.7.1. Structure Elucidation

1.Q. Checkpoint Quiz3 Qns

1.P.1. Practice: Structure Elucidation 1

1.P.2. Practice: Structure Elucidation 2

1.P.3. Practice: Structure Elucidation 3

2. Core Topic 3: Conjugated Systems

2.7hr

2.1.1. Aromaticity Theory9 min

2.1.2. Aromaticity Theory

2.1.3. Influence of Aromaticity in pKa/pKb3 min

2.1.4. Example: Acid/Base Strength 3 min

2.1.5. Example: Acid/Base Strength 3 min

2.2.1. Hydrohalogenation9 min

2.2.2. Example: Hydrohalogenation4 min

2.2.3. Example: Hydrohalogenation4 min

2.2.4. Acid-catalyzed Hydration9 min

2.2.5. Example: Acid-catalyzed Hydration4 min

2.2.6. Example: Acid-catalyzed Hydration 23 min

2.2.7. Hydroboration/Oxidation8 min

2.2.8. Example: Hydroboration 13 min

2.2.9. Example: Hydroboration 22 min

2.2.10. Halogenation13 min

2.2.11. Example: Halogenation 13 min

2.2.12. Example: Halogenation 22 min

2.2.13. Example: Halogenation3 min

2.2.14. Epoxidation8 min

2.2.15. Example: Epoxidation3 min

2.2.16. Example: Epoxides as Electrophiles8 min

2.2.17. Hydrogenation6 min

2.2.18. Example: Hydrogenation 13 min

2.2.19. Example: Hydrogenation 22 min

2.2.20. Example: Hydrogenation 31 min

2.2.21. Example: Hydrogenation with Isotopes of Hydrogen2 min

2.2.22. Carbocation Rearrangements6 min

2.2.23. Example: Carbocation Rearrangements3 min

2.2.24. Example: Carbocation Rearrangements3 min

2.2.25. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

2.3.1. UV-vis Spectroscopy5 min

2.3.2. UV-vis Study Sheet

2.4.1. Kinetic & Thermodynamic Products7 min

2.4.2. New Lesson

2.4.3. New Lesson

2.5.1. New Lesson4 min

2.5.2. New Lesson14 min

2.5.3. New Lesson

2.Q. Checkpoint Quiz9 Qns

3. Core Topic 4: Aromaticity EArS Reactions

48min

3.1.1. Aromaticity13 min

3.1.2. Summary Sheet: Naming Aromatic Rings

3.1.3. Example: Aromaticity5 min

3.1.4. Example: Aromaticity3 min

3.1.5. Practice: Aromaticity2 min

3.2.1. Electrophilic Aromatic Substitution Reactions 8 min

3.2.2. Electrophilic Aromatic Substitution4 min

3.3.1. Considerations for Electrophilic Aromatic Substitutions6 min

3.3.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

3.3.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

3.4.1. Summary Sheet: Aromaticity and Related Reactions

3.4.2. Summary Sheet: Naming Aromatic Rings

3.Q. Checkpoint Quiz4 Qns

4. Core Topic 5: Synthesis of Carbonyls and Carboxylic Acids

37min

4.I. Chapter Intro

4.1.1. Ozonolysis9 min

4.1.2. Example: Ozonolysis 12 min

4.1.3. Example: Ozonolysis4 min

4.2.1. Dihydroxylation5 min

4.2.2. Example: Dihydroxylation3 min

4.3.1. Oxidation to make Aldehydes4 min

4.3.2. Oxidation to make Ketones2 min

4.3.3. Oxidation of Aldehydes3 min

4.3.4. Example: Oxidation Reactions5 min

4.4.1. Summary Sheet: Reduction and Oxidation Reactions

5. Core Topic 6: Nucleophilic Additions to Carbonyls (AnCO)

1.7hr

5.1.1. Nomenclature and Physical Properties3 min

5.2.1. General Reactivity1 min

5.2.2. General Mechanism at the Carbonyl4 min

5.3.1. Reduction using NaBH42 min

5.3.2. Reduction using LiAlH44 min

5.3.3. Example: Reduction Reactions3 min

5.3.4. Example: Reductions Reactions5 min

5.4.1. The Grignard Reaction5 min

5.4.2. Cyanohydrin Formation3 min

5.4.3. Example: The Grignard Reaction2 min

5.4.4. Practice: The Grignard Reaction5 min

5.4.5. Wittig Reaction10 min

5.4.6. Horner-Wadsworth-Emmons-Reaction3 min

5.4.7. New Lesson

5.5.1. General Reactions with Oxygen Nucleophiles5 min

5.5.2. Hydrate Formation1 min

5.5.3. Acetal Formation2 min

5.5.4. Ketal Formation2 min

5.5.5. Hydrolysis of Acetals and Ketals3 min

5.5.6. General Mechanism with Oxygen Nucleophiles9 min

5.5.7. Stability of Hemiketals and Hemiacetals3 min

5.5.8. Practice: Ketals and Acetals as Protecting Groups2 min

5.5.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

5.5.11. Practice: Mechanism in Acetal and Ketal Formation3 min

5.5.12. Practice: Identifying Acetals/Aldehydes2 min

5.6.1. Synthesis and Hydrolysis of Imines7 min

5.6.2. Enamine Formation2 min

5.6.3. Mechanism of Imiine Formation4 min

5.6.4. Reductive Amination2 min

5.6.5. Practice: Imine Formation2 min

5.7.1. Study Sheet: Reaction Overview and Key Ideas

5.Q. Checkpoint Quiz4 Qns

6. Core Topic 7: Nucleophilic Additions - Elimination (SnCO)

53min

6.1.1. Carboxylic Acids2 min

6.1.2. Example: Carboxylic Acids5 min

6.1.3. Example: Carboxylic Acids2 min

6.2.1. Nomenclature and Physical Properties3 min

6.3.1. General Reactivity3 min

6.3.2. General Mechanism at the Carbonyl2 min

6.3.3. Practice: General Reactivity34 sec

6.3.4. Summary Sheet: Carboxylic Acid Reactivity

6.4.1. Acyl Halides3 min

6.4.2. Example: Acyl Halides2 min

6.4.3. Example: Acyl Halides 22 min

6.5.1. Synthesis of Anhydrides

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

6.5.3. Other Syntheses of Esters1 min

6.5.4. Transesterification2 min

6.5.5. Example: Esters and Anhydrides9 min

6.5.6. Example: Esters and Anhydrides 28 min

6.6.1. Formation of Amides from Acid Halides1 min

6.6.2. Example: Amides3 min

6.6.3. Example: Amides2 min

6.6.4. Practice: Peptide Bonds50 sec

6.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

6.7.2. Hydrolysis of Esters and Amides24 sec

6.8.1. Nucleophilic Acyl Substitutions

6.Q. Checkpoint Quiz13 Qns

7. Core Topic 8 & 9: Enols and Enolate Reactions

47min

7.I. Chapter Intro

7.1.1. Tautomerization8 min

7.1.2. Enolate Formation & Electrophilic Addition3 min

7.1.3. Kinetic vs. Thermodynamic Enolates5 min

7.1.4. The Aldol Reaction3 min

7.1.5. Mechanism of the Aldol Reaction5 min

7.1.6. The Retro-Aldol Reaction1 min

7.1.7. Mixed Aldol Reactions5 min

7.1.8. Example: The Aldol Reaction4 min

7.1.9. Practice: The Aldol Reaction2 min

7.2.1. Claisen Reactions3 min

7.2.2. Example: Claisen Reactions4 min

7.2.3. Example: Claisen Reactions2 min

7.2.4. Example: Dieckmann Condensation3 min

8. Core Topic 10: Reactions of Unsaturated Carbonyl Compounds

12min

8.I. Chapter Intro

8.1.1. Robinson Annulation12 min

8.1.2. Robinson Annulation Practice

Mock Exams

ME.1. Midterm - Mock Assessment38 Qns

ME.2. Final Exam - Mock Assessment32 Qns

ME.2 Final Exam - Mock Assessment

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