CHEM 2536

VT

Course Overview

Lessons & Practice

I. Welcome

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

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

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. Acid/Base Chemistry & Intro to Organic Reactions (Review)

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. Stereochemistry & Isomers (Review)

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. Reactions Review

2.3hr

5.I. Chapter Intro

5.1.1. Hydrohalogenation9 min

5.1.2. Example: Hydrohalogenation4 min

5.1.3. Example: Hydrohalogenation4 min

5.2.1. Acid-catalyzed Hydration9 min

5.2.2. Example: Acid-catalyzed Hydration4 min

5.2.3. Example: Acid-catalyzed Hydration 23 min

5.3.1. Hydroboration/Oxidation8 min

5.3.2. Example: Hydroboration 13 min

5.3.3. Example: Hydroboration 22 min

5.4.1. Halogenation13 min

5.4.2. Example: Halogenation 13 min

5.4.3. Example: Halogenation 22 min

5.4.4. Example: Halogenation3 min

5.5.1. Ozonolysis9 min

5.5.2. Example: Ozonolysis 12 min

5.5.3. Example: Ozonolysis4 min

5.6.1. Dihydroxylation5 min

5.6.2. Example: Dihydroxylation3 min

5.7.1. Epoxidation8 min

5.7.2. Example: Epoxidation3 min

5.7.3. Example: Epoxides as Electrophiles8 min

5.8.1. Hydrogenation6 min

5.8.2. Example: Hydrogenation 13 min

5.8.3. Example: Hydrogenation 22 min

5.8.4. Example: Hydrogenation 31 min

5.8.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

5.9.1. Carbocation Rearrangements6 min

5.9.2. Example: Carbocation Rearrangements3 min

5.9.3. Example: Carbocation Rearrangements3 min

5.10.1. Reactivity of Dienes (*coming soon)

5.10.2. 1,2- and 1,4-addition of HX to dienes (*coming soon)

5.12.1. Terpene Biosynthesis2 min

5.12.2. Example: Terpene Biosynthesis 12 min

5.12.3. Example: Terpene Biosynthesis4 min

5.13.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

5.P.1. Practice: Reaction Energy Diagrams

6. Nucleophilic Substitutions and Elimination Reactions (Review)

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. Reactions of Benzenes

48min

7.1.1. Aromaticity13 min

7.1.2. Summary Sheet: Naming Aromatic Rings

7.1.3. Example: Aromaticity5 min

7.1.4. Example: Aromaticity3 min

7.1.5. Practice: Aromaticity2 min

7.3.1. Electrophilic Aromatic Substitution Reactions 8 min

7.3.2. Electrophilic Aromatic Substitution4 min

7.4.1. Considerations for Electrophilic Aromatic Substitutions6 min

7.4.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

7.4.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

7.5.1. Summary Sheet: Aromaticity and Related Reactions

7.5.2. Summary Sheet: Naming Aromatic Rings

7.Q. Checkpoint Quiz4 Qns

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

1.9hr

8.1.1. Hydrogen Deficiency Index4 min

8.2.1. Infrared Spectroscopy12 min

8.2.2. Example: IR Spectroscopy2 min

8.2.3. Example: IR Spectroscopy52 sec

8.2.4. Practice Question: IR Spectroscopy1 min

8.2.5. Practice Question: IR Spectroscopy 21 min

8.3.1. Mass Spectrometry9 min

8.3.2. Example: Mass Spectrometry4 min

8.3.3. Example: Mass Spectrometry2 min

8.3.4. Example: Mass Spectrometry2 min

8.4.1. UV-vis Spectroscopy5 min

8.4.2. UV-vis Study Sheet

8.5.1. NMR Theory6 min

8.5.2. Example: Intro to NMR2 min

8.5.3. Example: Intro to NMR2 min

8.6.1. Hydrogen (1H NMR)20 min

8.6.2. Example: 1H NMR3 min

8.6.3. Example: 1H NMR6 min

8.6.4. Practice: 1H NMR 3 min

8.6.5. Practice Question: 1H NMR2 min

8.6.6. Practice Question: 1H NMR1 min

8.6.7. Practice Question4 min

8.7.1. Carbon (13C) NMR8 min

8.7.2. Example: 13C NMR3 min

8.7.3. Example: 13C NMR4 min

8.7.4. Practice: 13C NMR3 min

8.7.5. Example: 13C NMR3 min

8.8.1. Structure Elucidation

8.Q. Checkpoint Quiz3 Qns

8.P.1. Practice: Structure Elucidation 1

8.P.2. Practice: Structure Elucidation 2

8.P.3. Practice: Structure Elucidation 3

9. Carbonyls I & II & III

3hr

9.1.1. Nomenclature and Physical Properties3 min

9.2.1. General Reactivity1 min

9.2.2. General Mechanism at the Carbonyl4 min

9.3.1. The Grignard Reaction5 min

9.3.2. Cyanohydrin Formation3 min

9.3.3. Example: The Grignard Reaction2 min

9.3.4. Practice: The Grignard Reaction5 min

9.4.1. General Reactions with Oxygen Nucleophiles5 min

9.4.2. Hydrate Formation1 min

9.4.3. Acetal Formation2 min

9.4.4. Ketal Formation2 min

9.4.5. Hydrolysis of Acetals and Ketals3 min

9.4.6. General Mechanism with Oxygen Nucleophiles9 min

9.4.7. Stability of Hemiketals and Hemiacetals3 min

9.4.8. Practice: Ketals and Acetals as Protecting Groups2 min

9.4.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

9.4.11. Practice: Mechanism in Acetal and Ketal Formation3 min

9.4.12. Practice: Identifying Acetals/Aldehydes2 min

9.5.1. Synthesis and Hydrolysis of Imines7 min

9.5.2. Enamine Formation2 min

9.5.3. Mechanism of Imiine Formation4 min

9.5.4. Reductive Amination2 min

9.5.5. Practice: Imine Formation2 min

9.6.1. Tautomerization8 min

9.6.2. Enolate Formation3 min

9.6.3. Kinetic vs. Thermodynamic Enolates5 min

9.6.4. The Aldol Reaction3 min

9.6.5. Mechanism of the Aldol Reaction5 min

9.6.6. The Retro-Aldol Reaction1 min

9.6.7. Mixed Aldol Reactions5 min

9.6.8. Example: The Aldol Reaction4 min

9.6.9. Practice: The Aldol Reaction2 min

9.7.1. Study Sheet: Reaction Overview and Key Ideas

9.8.1. Carboxylic Acids2 min

9.8.2. Example: Carboxylic Acids5 min

9.8.3. Example: Carboxylic Acids2 min

9.9.1. Nomenclature and Physical Properties3 min

9.10.1. General Reactivity3 min

9.10.2. General Mechanism at the Carbonyl2 min

9.10.3. Practice: General Reactivity34 sec

9.10.4. Summary Sheet: Carboxylic Acid Reactivity

9.11.1. Acyl Halides3 min

9.11.2. Example: Acyl Halides2 min

9.11.3. Example: Acyl Halides 22 min

9.12.1. Synthesis of Anhydrides

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

9.12.3. Other Syntheses of Esters1 min

9.12.4. Transesterification2 min

9.12.5. Example: Esters and Anhydrides9 min

9.12.6. Example: Esters and Anhydrides 28 min

9.13.1. Formation of Amides from Acid Halides1 min

9.13.2. Example: Amides3 min

9.13.3. Example: Amides2 min

9.13.4. Practice: Peptide Bonds50 sec

9.14.1. Hydrolysis of Acid Halides and Anhydrides38 sec

9.14.2. Hydrolysis of Esters and Amides24 sec

9.15.1. Claisen Reactions3 min

9.15.2. Example: Claisen Reactions4 min

9.15.3. Example: Claisen Reactions2 min

9.15.4. Example: Dieckmann Condensation3 min

9.16.1. Nucleophilic Acyl Substitutions

9.Q. Checkpoint Quiz4 Qns

10. Carbohydrate Chemistry

56min

10.1.1. Straight Chain Nomenclature7 min

10.1.2. Cyclization of Monosaccharides5 min

10.1.3. Cyclic Nomenclature6 min

10.1.4. Glycosidic Bonds2 min

10.1.5. Example: Carbohydrate Nomenclature3 min

10.1.6. Example: Carbohydrate Nomenclature (Glycosides)4 min

10.2.1. Converting Fischer Structures4 min

10.2.2. Example: Converting Fischer Structures3 min

10.2.3. Example: Converting Fischer Structures3 min

10.2.4. Practice Question: Converting Fischer Projections2 min

10.3.1. Carbohydrate Reactions: Formation of Glycosidic Bonds4 min

10.3.2. Carbohydrate Reactions: Hydrolysis of Glycosidic Bonds1 min

10.3.3. Carbohydrate Reactions: Reducing Sugars2 min

10.3.4. Practice: Carbohydrates in Solution1 min

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

10.3.6. Example: Identifying Reducing Sugars2 min

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

10.4.1. Carbohydrates

10.Q. Checkpoint Quiz15 Qns

11. Amino Acids, Peptides, and Proteins (*coming soon)

11.1.1. Structure of Amino Acids (*coming soon)

11.1.2. pKa of Amino Acids (*coming soon)

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

11.2.1. Lipids (*coming soon)

11.2.2. Sterols (*coming soon)

12. Polymer Chemistry

1.1hr

12.I. Chapter Intro

12.1.1. Radical Stability4 min

12.1.2. Example: Radical Stability3 min

12.1.3. Example: Radical Stability1 min

12.1.4. Practice: Radical Stability1 min

12.2.1. Radical Reactions: Radical Halogenation7 min

12.2.2. Radical Reactions: Hydrohalogenation with a Peroxide7 min

12.2.3. Practice: Radical Reactions2 min

12.2.4. Practice: Radical Reactions2 min

12.2.5. Practice: Radical Reactions3 min

12.3.1. Polymers Theory

12.3.2. Polymer Formation Theory

12.3.3. Condensation Polymerization6 min

12.3.4. Addition Polymerization3 min

12.3.5. Polymer Reaction Mechanisms23 min

12.3.6. Radical Polymerization Practice

12.3.7. Special Types of Polymers3 min

Mock Exams

ME.1. Midterm Exam 2 - Mock Assessment14 Qns

ME.2. Midterm Exam 3 - Mock Assessment32 Qns

ME.3. Final Exam - Mock Assessment23 Qns

ME.2 Midterm Exam 3 - Mock Assessment

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