CHEM 281

Queen's

Course Overview

Grade Boosters

Lessons & Practice

I. Welcome

1. What is a molecule?

1.3hr

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. Lewis Structures and Formal Charges9 min

1.2.2. How to Draw Lewis Structures5 min

1.2.3. Example: Lewis Structures5 min

1.2.4. Example: Lewis Structures5 min

1.2.5. Practice: Lewis Structures2 min

1.2.6. Practice: Lewis Structures5 min

1.3.1. Bonding Models

1.3.2. Practice: Valence Bond Theory/Hybridization3 min

1.4.1. Valence Bond Theory and Hybridization7 min

1.4.2. Example: Valence Bond Theory/Hybridization5 min

1.5.1. Molecular Orbital Theory4 min

1.6.1. Bonding in Delocalized Systems3 min

1.6.2. Example: Resonance Structures6 min

1.7.1. VSEPR Theory5 min

1.7.2. Example: VSEPR2 min

1.7.3. Example: VSEPR3 min

1.7.4. Practice: VSEPR4 min

1.8.1. Summary Sheet: The Basics

2. Physical Properties and Molecular Structure (Including Polarity)

43min

2.1.1. Polar Bonds6 min

2.1.2. Example: Polar Bonds3 min

2.1.3. Example: Polar Bonds 2 min

2.1.4. Practice: Polar Bonds 50 sec

2.2.1. Intermolecular Forces4 min

2.2.2. Melting and Boiling Point Comparison4 min

2.2.3. Example: Intermolecular Forces3 min

2.2.4. Example: Intermolecular Forces2 min

2.2.5. Practice: Intermolecular Forces1 min

2.2.6. Summary Sheet: Intermolecular Forces

2.3.1. Summary Sheet: Common Organic Functional Groups

2.3.2. Example: Functional Groups 2 min

2.4.1. Infrared Spectroscopy12 min

2.4.2. Example: IR Spectroscopy2 min

2.4.3. Example: IR Spectroscopy52 sec

2.4.4. Practice Question: IR Spectroscopy1 min

2.4.5. Practice Question: IR Spectroscopy 21 min

2.P.1. Intermolecular forces: Strength

2.P.2. Intermolecular forces: Strength

2.P.3. Intermolecular forces

2.P.4. Intermolecular Forces

3. An Introduction to Organic Reactions and their Mechanisms - Acids and Bases

1.2hr

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

3.5.1. General Terminology4 min

3.5.2. Nucleophiles4 min

3.5.3. Electrophiles2 min

3.5.4. Leaving Groups4 min

3.5.5. Substitution vs. Elimination2 min

3.5.6. Example: Substitution vs. Elimination3 min

4. Nomenclature and General Properties of Alkanes, Cycloalkanes, Alkenes, and Alkynes

52min

4.1.1. IUPAC Systematic Naming Theory15 min

4.1.2. Example: Converting Names to Structures2 min

4.1.3. Example: IUPAC Systematic Naming2 min

4.1.4. Example: IUPAC Systematic Naming2 min

4.1.5. Practice: IUPAC Systematic Naming2 min

4.1.6. Practice: IUPAC Systematic Naming2 min

4.1.7. Summary Sheet: IUPAC Naming

4.2.1. Drawing Organic Compounds in 3D5 min

4.2.2. Example: 3-D Notation2 min

4.2.3. Example: 3-D Notation2 min

4.2.4. Summary Sheet: Drawing in 3-Dimensions

4.2.5. Conformational Isomers6 min

4.2.6. Example: Conformational Isomers3 min

4.2.7. Cyclohexane Chair Conformations4 min

4.3.1. Index of Hydrogen Deficiency4 min

5. Stereochemistry – Chiral Molecules

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

6. Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

48min

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

6.2.5. Carbocation stability

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. Summary Sheet: Substitution Reactions

6.P.1. Practice: Substitution Question 2

7. Alkenes and Alkynes I – Properties and Synthesis. Elimination Reactions of Alkyl Halides and Alcohols

48min

7.1.1. Molecularity and Rate43 sec

7.1.2. Structural Requirements52 sec

7.1.3. E1 Mechanism3 min

7.2.1. Molecularity and Rate45 sec

7.2.2. Structural Requirements2 min

7.2.3. Synthesis of Alkynes1 min

7.2.4. E2 Mechanism3 min

7.3.1. Selectivity in Elimination Reactions - E2 Reactions8 min

7.3.2. Selectivity in Elimination Reactions - E1 Reactions4 min

7.3.3. Example: Selectivity in Elimination Reactions6 min

7.3.4. Carbocation Rearrangements

7.4.1. Favouring Elimination over Subsitution5 min

7.5.1. Summary Sheet: Substitution Reactions

7.5.2. Summary Sheet: Elimination Reactions

7.6.1. Dehydrohalogenation of Alkyl Halides

7.6.2. Acid-Catalyzed Dehydration of Alcohols

7.6.3. Synthesis of Alkynes by Dehydrohalogenation of Vicinal Dihalides

7.6.4. Synthesis of Alkynes by Dehydrohalogenation of Geminal Dihalides

7.6.5. Acetylide Anions for Carbon-Carbon Bond Formation

7.7.1. Hydrogenation6 min

7.7.2. Example: Hydrogenation 13 min

7.7.3. Example: Hydrogenation 22 min

7.7.4. Example: Hydrogenation 31 min

7.7.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

7.P.1. Practice: Substitution Question 2

7.P.2. Practice: Elimination Question 1

7.P.3. Practice: Elimination Question 2

8. Addition Reactions (Including Oxidation) of Alkenes and Alkynes

2hr

8.1.1. Hydrohalogenation9 min

8.1.2. Example: Hydrohalogenation4 min

8.1.3. Example: Hydrohalogenation4 min

8.2.1. Acid-catalyzed Hydration9 min

8.2.2. Example: Acid-catalyzed Hydration4 min

8.2.3. Example: Acid-catalyzed Hydration 23 min

8.3.1. Hydroboration/Oxidation8 min

8.3.2. Example: Hydroboration 13 min

8.3.3. Example: Hydroboration 22 min

8.4.1. Halogenation13 min

8.4.2. Example: Halogenation 13 min

8.4.3. Example: Halogenation 22 min

8.4.4. Example: Halogenation3 min

8.5.1. Ozonolysis9 min

8.5.2. Example: Ozonolysis 12 min

8.5.3. Example: Ozonolysis4 min

8.6.1. Dihydroxylation5 min

8.6.2. Example: Dihydroxylation3 min

8.7.1. Epoxidation8 min

8.7.2. Example: Epoxidation3 min

8.7.3. Example: Epoxides as Electrophiles8 min

8.8.1. Carbocation Rearrangements6 min

8.8.2. Example: Carbocation Rearrangements3 min

8.8.3. Example: Carbocation Rearrangements3 min

8.9.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

8.10.1. Oxymercuration Reactions

8.11.1. Halohydrin Formation

8.12.1. Oxidative Cleavage with Basic Potassium Permanganate

9. Alcohols and Ethers

21min

9.1.1. Physical Properties and Naming

9.2.1. Alcohol Reactivity

9.3.1. SN1/SN2 Reactions of Alkyl Halides (Review)

9.3.2. Electrophilic Addition to Alkenes: Acid-catalyzed Hydration (Review)

9.3.3. Electrophilic Addition to Alkenes: Hydroboration/Oxidation (Review)

9.3.4. Electrophilic Addition to Alkenes: Dihydroxylation (Review)

9.3.5. Oxymercuration Reactions (Review)

9.4.1. Halogenation of Alcohols

9.4.2. Elimination of Alcohols to Alkenes

9.5.1. Overview of Ethers

9.5.2. Williamson Ether Synthesis8 min

9.5.3. Stereochemistry of Epoxide Formation and Opening13 min

Mock Exams

ME.1. Midterm Test - Mock Assessment38 Qns

ME.2. Final Exam - Mock Assessment89 Qns

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