CHM 2120

uOttawa

Course Overview

Lessons & Practice

I. Welcome

1. CHM 1321 Review: Lewis Structures, Bonding, Orbitals

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. CHM 1321 Review: 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. CHM 1321 Review: Acid/Base Chemistry

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. CHM 1321 Review: Stereochemistry & Isomers

1.5hr

4.1.1. Summary Sheet: Isomers Flowchart

4.2.1. Constitutional Isomers5 min

4.2.2. Example: Constitutional Isomers4 min

4.2.3. Example: Constitutional Isomers3 min

4.3.1. Conformational Isomers6 min

4.3.2. Example: Conformational Isomers3 min

4.4.1. Geometric or Cis/Trans Isomers6 min

4.4.2. Example: Geometric Isomers4 min

4.4.3. Practice: Geometric Isomers 2 min

4.5.1. Chiral Molecules5 min

4.5.2. Cahn-Ingold-Prelog Rules4 min

4.5.3. Assigning R and S Nomenclature4 min

4.5.4. Example: Stereochemistry7 min

4.5.5. Example: Stereochemistry 24 min

4.5.6. Practice: Stereochemistry 2 min

4.5.7. Practice: Stereochemistry1 min

4.6.1. Optical Isomers13 min

4.6.2. Example: Optical Isomers3 min

4.6.3. Example: Optical Isomers 23 min

4.6.4. Practice: Optical Isomers 1 min

4.7.1. Summary Sheet: IUPAC Naming

4.7.2. Summary Sheet: Naming Molecules with Stereochemistry

4.7.3. Example: Naming Molecules with Stereochemistry4 min

4.7.4. Example: Naming Molecules with Stereochemistry2 min

4.7.5. Practice: Naming Molecules with Stereochemistry2 min

4.8.1. Summary Sheet: Stereochemistry

4.8.2. Summary Sheet: Determining Maximum Number of Stereoisomers

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

4.Q. Checkpoint Quiz10 Qns

5. CHM 1321 Review: Aromaticity

49min

5.1.1. Aromaticity Theory9 min

5.1.2. Cheetsheet - Naming Aromatic Rings

5.1.3. Example: Aromaticity (1)8 min

5.1.4. Example: Aromaticity (2)6 min

5.1.5. Practice: Aromaticity

5.2.1. Electrophilic Aromatic Substitution Reactions 5 min

5.2.2. Electrophilic Aromatic Substitution2 min

5.3.1. Considerations for Electrophilic Aromatic Substitutions20 min

5.3.2. Directing Groups in Electrophilic Aromatic Subsitution

5.3.3. Directing Groups in Electrophilic Aromatic Substitution

5.4.1. Reactions Overview and Key Ideas

5.4.2. Cheatsheet - Naming Aromatic Rings

5.5.1. Arenes4 Qns

6. Nucleophilic Substitutions and Elimination Reactions

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. The Williamson Ether Synthesis (*coming soon)

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

6.8.1. Molecularity and Rate43 sec

6.8.2. Structural Requirements52 sec

6.8.3. E1 Mechanism3 min

6.9.1. Molecularity and Rate45 sec

6.9.2. Structural Requirements2 min

6.9.3. Synthesis of Alkynes1 min

6.9.4. E2 Mechanism3 min

6.10.1. Selectivity in Elimination Reactions - E2 Reactions8 min

6.10.2. Selectivity in Elimination Reactions - E1 Reactions4 min

6.10.3. Example: Selectivity in Elimination Reactions6 min

6.11.1. Favouring Elimination over Subsitution5 min

6.12.1. Summary Sheet: Substitution Reactions

6.12.2. Summary Sheet: Elimination Reactions

6.Q. Checkpoint Quiz13 Qns

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

1.2hr

7.1.1. Hydrogen Deficiency Index4 min

7.2.1. Infrared Spectroscopy12 min

7.2.2. Example: IR Spectroscopy2 min

7.2.3. Example: IR Spectroscopy52 sec

7.2.4. Practice Question: IR Spectroscopy1 min

7.2.5. Practice Question: IR Spectroscopy 21 min

7.3.1. NMR Theory6 min

7.3.2. Example: Intro to NMR2 min

7.3.3. Example: Intro to NMR2 min

7.4.1. Hydrogen (1H NMR)20 min

7.4.2. Example: 1H NMR3 min

7.4.3. Example: 1H NMR6 min

7.4.4. Practice: 1H NMR 3 min

7.4.5. Practice Question: 1H NMR2 min

7.4.6. Practice Question: 1H NMR1 min

7.4.7. Practice Question4 min

7.5.1. Structure Elucidation

7.Q. Checkpoint Quiz3 Qns

7.P.1. Practice: Structure Elucidation 1

7.P.2. Practice: Structure Elucidation 2

7.P.3. Practice: Structure Elucidation 3

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

1.9hr

8.1.1. Nomenclature and Physical Properties3 min

8.2.1. General Reactivity1 min

8.2.2. General Mechanism at the Carbonyl4 min

8.3.1. The Grignard Reaction5 min

8.3.2. Cyanohydrin Formation3 min

8.3.3. Example: The Grignard Reaction2 min

8.3.4. Practice: The Grignard Reaction5 min

8.4.1. General Reactions with Oxygen Nucleophiles5 min

8.4.2. Hydrate Formation1 min

8.4.3. Acetal Formation2 min

8.4.4. Ketal Formation2 min

8.4.5. Hydrolysis of Acetals and Ketals3 min

8.4.6. General Mechanism with Oxygen Nucleophiles9 min

8.4.7. Stability of Hemiketals and Hemiacetals3 min

8.4.8. Practice: Ketals and Acetals as Protecting Groups2 min

8.4.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

8.4.11. Practice: Mechanism in Acetal and Ketal Formation3 min

8.4.12. Practice: Identifying Acetals/Aldehydes2 min

8.5.1. Synthesis and Hydrolysis of Imines7 min

8.5.2. Enamine Formation2 min

8.5.3. Mechanism of Imiine Formation4 min

8.5.4. Reductive Amination2 min

8.5.5. Practice: Imine Formation2 min

8.6.1. Tautomerization8 min

8.6.2. Enolate Formation3 min

8.6.3. Kinetic vs. Thermodynamic Enolates5 min

8.6.4. The Aldol Reaction3 min

8.6.5. Mechanism of the Aldol Reaction5 min

8.6.6. The Retro-Aldol Reaction1 min

8.6.7. Mixed Aldol Reactions5 min

8.6.8. Example: The Aldol Reaction4 min

8.6.9. Practice: The Aldol Reaction2 min

8.7.1. Study Sheet: Reaction Overview and Key Ideas

8.Q. Checkpoint Quiz4 Qns

9. Carboxylic Acid Derivatives (Nucleophilic Acyl Substitutions)

1.1hr

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. Claisen Reactions3 min

9.8.2. Example: Claisen Reactions4 min

9.8.3. Example: Claisen Reactions2 min

9.8.4. Example: Dieckmann Condensation3 min

9.9.1. Nucleophilic Acyl Substitutions

9.Q. Checkpoint Quiz13 Qns

10. Reduction and Oxidation Reactions: Further Reactions (or Synthesis) of Carbonyl Derivatives

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

Mock Exams

ME.1. Midterm 1 - Mock Assessment40 Qns

ME.2. Midterm 2 - Mock Assessment43 Qns

ME.3. Final Exam - Mock Assessment104 Qns

ME.1 Midterm 1 - Mock Assessment

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