CHM249H1

U of T

Course Overview

Lessons & Practice

I. Welcome

2 min

1. 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. Intro to Orgo (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. Stereochemistry & Isomers

1.5hr

3.1.1. Summary Sheet: Isomers Flowchart

3.2.1. Constitutional Isomers5 min

3.2.2. Example: Constitutional Isomers4 min

3.2.3. Example: Constitutional Isomers3 min

3.3.1. Conformational Isomers6 min

3.3.2. Example: Conformational Isomers3 min

3.4.1. Geometric or Cis/Trans Isomers6 min

3.4.2. Example: Geometric Isomers4 min

3.4.3. Practice: Geometric Isomers 2 min

3.5.1. Chiral Molecules5 min

3.5.2. Cahn-Ingold-Prelog Rules4 min

3.5.3. Assigning R and S Nomenclature4 min

3.5.4. Example: Stereochemistry7 min

3.5.5. Example: Stereochemistry 24 min

3.5.6. Practice: Stereochemistry 2 min

3.5.7. Practice: Stereochemistry1 min

3.6.1. Optical Isomers13 min

3.6.2. Example: Optical Isomers3 min

3.6.3. Example: Optical Isomers 23 min

3.6.4. Practice: Optical Isomers 1 min

3.7.1. Summary Sheet: IUPAC Naming

3.7.2. Summary Sheet: Naming Molecules with Stereochemistry

3.7.3. Example: Naming Molecules with Stereochemistry4 min

3.7.4. Example: Naming Molecules with Stereochemistry2 min

3.7.5. Practice: Naming Molecules with Stereochemistry2 min

3.8.1. Summary Sheet: Stereochemistry

3.8.2. Summary Sheet: Determining Maximum Number of Stereoisomers

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

3.Q. Checkpoint Quiz10 Qns

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

1.9hr

4.1.1. Hydrogen Deficiency Index4 min

4.2.1. Infrared Spectroscopy12 min

4.2.2. Example: IR Spectroscopy2 min

4.2.3. Example: IR Spectroscopy52 sec

4.2.4. Practice Question: IR Spectroscopy1 min

4.2.5. Practice Question: IR Spectroscopy 21 min

4.3.1. Mass Spectrometry9 min

4.3.2. Example: Mass Spectrometry4 min

4.3.3. Example: Mass Spectrometry2 min

4.3.4. Example: Mass Spectrometry2 min

4.4.1. UV-vis Spectroscopy5 min

4.4.2. UV-vis Study Sheet

4.5.1. NMR Theory6 min

4.5.2. Example: Intro to NMR2 min

4.5.3. Example: Intro to NMR2 min

4.6.1. Hydrogen (1H NMR)20 min

4.6.2. Example: 1H NMR3 min

4.6.3. Example: 1H NMR6 min

4.6.4. Practice: 1H NMR 3 min

4.6.5. Practice Question: 1H NMR2 min

4.6.6. Practice Question: 1H NMR1 min

4.6.7. Practice Question4 min

4.7.1. Carbon (13C) NMR8 min

4.7.2. Example: 13C NMR3 min

4.7.3. Example: 13C NMR4 min

4.7.4. Practice: 13C NMR3 min

4.7.5. Example: 13C NMR3 min

4.8.1. Structure Elucidation

4.Q. Checkpoint Quiz3 Qns

4.P.1. Practice: Structure Elucidation 1

4.P.2. Practice: Structure Elucidation 2

4.P.3. Practice: Structure Elucidation 3

5. Kinetics

2hr

5.1.1. Introduction to Kinetics1 min

5.2.1. Reaction Rates 3 min

5.2.2. Measuring Reaction Rates4 min

5.2.3. Practice: Rate of Reaction6 min

5.2.4. Practice: Rate of Reaction5 min

5.3.1. Rate Laws2 min

5.3.2. Example: Determining Reaction Order44 sec

5.3.3. Determining the Rate Law From Experimental Data 10 min

5.3.4. Shortcut to Find Units of k Quicker 3 min

5.3.5. Practice: Experimental Rate Law 6 min

5.3.6. Practice: Determining Rate Law Exponents

5.3.7. Practice: Rate Law1 min

5.3.8. Practice: Units of the Rate Constant, K5 min

5.4.1. Integrated Rate Laws for Various Orders 7 min

5.4.2. Example: Plotting a Straight Line with the Integrated Rate Laws

5.4.3. Practice: Integrated Rate Laws Practice

5.4.4. Integrated Rate Laws Cheatsheet

5.4.5. First Order Reactions

5.4.6. Second Order Reactions

5.5.1. Arrhenius Equation1 min

5.5.2. Example: Arrhenius Equation

5.5.3. Example: Arrhenius Equation1 min

5.5.4. Practice: Arrhenius Equation

5.6.1. How Do We Measure Ea39 sec

5.6.2. Practice: Determining the Activation Energy39 sec

5.7.1. 3 Neccessary Steps For a Reaction to Occur 1 min

5.7.2. Collision Theory7 min

5.7.3. Collision Theory Represented By A Graph2 min

5.7.4. Transition State Theory 4 min

5.7.5. Additional Notes on the Arrhenius Equation 9 min

5.8.1. Reactions Mechanisms – Elementary Reactions4 min

5.8.2. Example: Reactions Mechanisms – Elementary Steps

5.8.3. Rate Determining Step Introduction 5 min

5.8.4. Example: Rate Determining Step14 min

5.8.5. Practice: Rate of A Reaction

5.8.6. Practice: Reaction Coordinate Diagram4 min

5.8.7. Practice: Mechanism

5.9.1. Catalysts3 min

5.9.2. Enzymes4 min

5.9.3. Example: Identifying a Catalyst Vs an Intermediate In a Mechanism 2 min

5.9.4. Example: Catalysts 224 sec

6. Spontaneity and Gibbs Free Energy

20min

6.1.1. Gibbs Free Energy and Spontaneity (w/chemical potential)2 min

6.1.2. Spontaneity 7 min

6.1.3. Example: Spontaneity of a Reaction

6.1.4. Predicting Spontaneity Based off Entropy2 min

6.2.1. Chemical Equilibrium and ΔG Equations5 min

6.2.2. DeltaGo and K 3 min

6.2.3. Example

6.2.4. Chemical Equilibrium and ΔG Practice

6.2.5. Chemical Equilibrium and ΔG Practice #2

6.2.6. Chemical Equilibrium and ΔG Practice #3

6.2.7. Van't Hoff Practice Problem

7. Acid/Base Chemistry & Intro to Organic Reactions

56min

7.1.1. Acid/Base Equilibrium Fundamentals - Use of Acids and Bases in Organic Chemistry4 min

7.1.2. Key Definitions in Acids/Bases5 min

7.1.3. Acid/Base Equilibrium Constants2 min

7.1.4. Example: Acid/Base Arrows 3 min

7.2.1. Factors Influencing Acid/Base Strength2 min

7.2.2. Electronegativity1 min

7.2.3. Atom Size2 min

7.2.4. Resonance3 min

7.2.5. Hybridization3 min

7.2.6. Induction3 min

7.2.7. Aromaticity3 min

7.2.8. Example: Acid/Base Strength 3 min

7.2.9. Example: Acid/Base Strength 3 min

7.2.10. Practice: Acid/Base Equilibria 2 min

7.2.11. Practice: Acid/Base Equilibria 2 min

7.3.1. Important pKas You Should Know4 min

7.3.2. Relationship Between pH and pKa2 min

7.3.3. Amino Acids at Different pHs3 min

7.3.4. Practice: Amino Acids in Solution3 min

7.3.5. Practice: Amino Acids in Solution3 min

7.3.6. Summary Sheet: Amino Acids in Solution of Various pH

7.3.7. Summary Sheet: pKa's of Common Molecules

7.4.1. Summary Sheet: Chemical Equilibria and Acid/Base Chemistry

7.Q. Checkpoint Quiz15 Qns

8. Electrophilic Addition Reactions to Alkenes/Alkynes

2.3hr

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. Hydrogenation6 min

8.8.2. Example: Hydrogenation 13 min

8.8.3. Example: Hydrogenation 22 min

8.8.4. Example: Hydrogenation 31 min

8.8.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

8.9.1. Carbocation Rearrangements6 min

8.9.2. Example: Carbocation Rearrangements3 min

8.9.3. Example: Carbocation Rearrangements3 min

8.10.1. Reactivity of Dienes (*coming soon)

8.10.2. 1,2- and 1,4-addition of HX to dienes (*coming soon)

8.12.1. Terpene Biosynthesis2 min

8.12.2. Example: Terpene Biosynthesis 12 min

8.12.3. Example: Terpene Biosynthesis4 min

8.13.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

8.Q. Checkpoint Quiz9 Qns

8.P.1. Practice: Reaction Energy Diagrams

9. Aromaticity (Arenes)

48min

9.1.1. Aromaticity13 min

9.1.2. Summary Sheet: Naming Aromatic Rings

9.1.3. Example: Aromaticity5 min

9.1.4. Example: Aromaticity3 min

9.1.5. Practice: Aromaticity2 min

9.3.1. Electrophilic Aromatic Substitution Reactions 8 min

9.3.2. Electrophilic Aromatic Substitution4 min

9.4.1. Considerations for Electrophilic Aromatic Substitutions6 min

9.4.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

9.4.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

9.5.1. Summary Sheet: Aromaticity and Related Reactions

9.5.2. Summary Sheet: Naming Aromatic Rings

9.Q. Checkpoint Quiz4 Qns

10. Nucleophilic Substitutions and Elimination Reactions

1.4hr

10.1.1. General Terminology4 min

10.1.2. Nucleophiles4 min

10.1.3. Electrophiles2 min

10.1.4. Leaving Groups4 min

10.1.5. Substitution vs. Elimination2 min

10.1.6. Example: Substitution vs. Elimination3 min

10.2.1. Molecularity and Rate57 sec

10.2.2. Structural Requirements1 min

10.2.3. SN1 Mechanism4 min

10.2.4. Practice: Sn1 Reaction1 min

10.3.1. Molecularity and Rate1 min

10.3.2. Structural Requirements2 min

10.3.3. SN2 Mechanism4 min

10.3.4. Practice: Sn2 Reaction1 min

10.4.1. Stereochemistry in Substitution Reactions2 min

10.5.1. Leaving Group Ability4 min

10.5.2. Example: Alcohol as a Leaving Group2 min

10.6.1. Solvent Effects in Substitution Reactions6 min

10.7.1. The Williamson Ether Synthesis (*coming soon)

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

10.8.1. Molecularity and Rate43 sec

10.8.2. Structural Requirements52 sec

10.8.3. E1 Mechanism3 min

10.9.1. Molecularity and Rate45 sec

10.9.2. Structural Requirements2 min

10.9.3. Synthesis of Alkynes1 min

10.9.4. E2 Mechanism3 min

10.10.1. Selectivity in Elimination Reactions - E2 Reactions8 min

10.10.2. Selectivity in Elimination Reactions - E1 Reactions4 min

10.10.3. Example: Selectivity in Elimination Reactions6 min

10.11.1. Favouring Elimination over Subsitution5 min

10.12.1. Summary Sheet: Substitution Reactions

10.12.2. Summary Sheet: Elimination Reactions

10.Q. Checkpoint Quiz13 Qns

10.P.1. Practice: Substitution Question 1

10.P.2. Practice: Substitution Question 2

10.P.3. Practice: Elimination Question 1

10.P.4. Practice: Elimination Question 2

10.P.5. Practice: Elimination Question 3

11. Radical Reactions

30min

11.1.1. Radical Stability4 min

11.1.2. Example: Radical Stability3 min

11.1.3. Example: Radical Stability1 min

11.1.4. Practice: Radical Stability1 min

11.2.1. Radical Reactions: Radical Halogenation7 min

11.2.2. Radical Reactions: Hydrohalogenation with a Peroxide7 min

11.2.3. Practice: Radical Reactions2 min

11.2.4. Practice: Radical Reactions2 min

11.2.5. Practice: Radical Reactions3 min

11.3.1. Summary Sheet: Radical Reactions

11.Q. Checkpoint Quiz7 Qns

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

12.1.1. Structure of Amino Acids (*coming soon)

12.1.2. pKa of Amino Acids (*coming soon)

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

12.2.1. Lipids (*coming soon)

12.2.2. Sterols (*coming soon)

13. Chemistry of Amines

18min

13.1.1. Amidation1 min

13.1.2. Alkylating Amines5 min

13.1.3. Reductive Amination2 min

13.1.4. Imines and Amines Theory

13.1.5. Naming and Properties of Amines10 min

14. Reduction and Oxidation Reactions

42min

14.1.1. Structure and Reactivity (*coming soon)

14.2.1. Thiols (*coming soon)

14.2.2. Sulfides (*coming soon)

14.3.1. Oxidation to make Aldehydes4 min

14.3.2. Oxidation to make Ketones2 min

14.3.3. Oxidation of Aldehydes3 min

14.3.4. Example: Oxidation Reactions5 min

14.4.1. Reduction using NaBH42 min

14.4.2. Reduction using LiAlH44 min

14.4.3. Example: Reduction Reactions3 min

14.4.4. Example: Reductions Reactions5 min

14.5.1. Hydrogenation6 min

14.5.2. Example: Hydrogenation3 min

14.5.3. Example: Hydrogenation2 min

14.5.4. Example: Hydrogenation1 min

14.5.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

14.6.1. Summary Sheet: Reduction and Oxidation Reactions

14.Q. Checkpoint Quiz7 Qns

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

1.9hr

15.1.1. Nomenclature and Physical Properties3 min

15.2.1. General Reactivity1 min

15.2.2. General Mechanism at the Carbonyl4 min

15.3.1. The Grignard Reaction5 min

15.3.2. Cyanohydrin Formation3 min

15.3.3. Example: The Grignard Reaction2 min

15.3.4. Practice: The Grignard Reaction5 min

15.4.1. General Reactions with Oxygen Nucleophiles5 min

15.4.2. Hydrate Formation1 min

15.4.3. Acetal Formation2 min

15.4.4. Ketal Formation2 min

15.4.5. Hydrolysis of Acetals and Ketals3 min

15.4.6. General Mechanism with Oxygen Nucleophiles9 min

15.4.7. Stability of Hemiketals and Hemiacetals3 min

15.4.8. Practice: Ketals and Acetals as Protecting Groups2 min

15.4.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

15.4.11. Practice: Mechanism in Acetal and Ketal Formation3 min

15.4.12. Practice: Identifying Acetals/Aldehydes2 min

15.5.1. Synthesis and Hydrolysis of Imines7 min

15.5.2. Enamine Formation2 min

15.5.3. Mechanism of Imiine Formation4 min

15.5.4. Reductive Amination2 min

15.5.5. Practice: Imine Formation2 min

15.6.1. Tautomerization8 min

15.6.2. Enolate Formation3 min

15.6.3. Kinetic vs. Thermodynamic Enolates5 min

15.6.4. The Aldol Reaction3 min

15.6.5. Mechanism of the Aldol Reaction5 min

15.6.6. The Retro-Aldol Reaction1 min

15.6.7. Mixed Aldol Reactions5 min

15.6.8. Example: The Aldol Reaction4 min

15.6.9. Practice: The Aldol Reaction2 min

15.7.1. Study Sheet: Reaction Overview and Key Ideas

15.Q. Checkpoint Quiz4 Qns

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. Carboxylic Acid Derivatives (Nucleophilic Acyl Substitutions)

1.1hr

17.1.1. Carboxylic Acids2 min

17.1.2. Example: Carboxylic Acids5 min

17.1.3. Example: Carboxylic Acids2 min

17.2.1. Nomenclature and Physical Properties3 min

17.3.1. General Reactivity3 min

17.3.2. General Mechanism at the Carbonyl2 min

17.3.3. Practice: General Reactivity34 sec

17.3.4. Summary Sheet: Carboxylic Acid Reactivity

17.4.1. Acyl Halides3 min

17.4.2. Example: Acyl Halides2 min

17.4.3. Example: Acyl Halides 22 min

17.5.1. Synthesis of Anhydrides

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

17.5.3. Other Syntheses of Esters1 min

17.5.4. Transesterification2 min

17.5.5. Example: Esters and Anhydrides9 min

17.5.6. Example: Esters and Anhydrides 28 min

17.6.1. Formation of Amides from Acid Halides1 min

17.6.2. Example: Amides3 min

17.6.3. Example: Amides2 min

17.6.4. Practice: Peptide Bonds50 sec

17.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

17.7.2. Hydrolysis of Esters and Amides24 sec

17.8.1. Claisen Reactions3 min

17.8.2. Example: Claisen Reactions4 min

17.8.3. Example: Claisen Reactions2 min

17.8.4. Example: Dieckmann Condensation3 min

17.9.1. Nucleophilic Acyl Substitutions

17.Q. Checkpoint Quiz13 Qns

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Unanswered

Scarlet K

Are there any tips for identifying equivalent hydrogens in a H NMR?

Answered

Anonymous

is there anything on skeletal structures

Rex H

Instructor

Great question! 

There is a bunch of content on skeletal answers, check our our gradebooster reviews as well as our subscription content for more info! 

Hope this helps! 

Answered

David K

how many hours must one devote/wk,? assigned homework? random quizes/mini-tests?

Emma D

Instructor

Hi David - this is a good question.  I have some general advice here.  First, save yourself time in the long run and invest 10 minutes after each class to make flashcards on things like functional groups, reagents, reactions, pKas, etc.  Second, you should plan to do 2 hours of practice for each 1 hour of class (so if you have three 1 hour classes a week, that would mean that you do 6 hours of homework a week).  Finally, as test time comes closer, you want to increase this and add an additional 10 or so hours for midterm preparation and 25 hours for final exam preparation.

Be careful for organic chemistry -- it's a course you cannot cram for.  If you invest short periods of time frequently over the semester you will get more from class and studying and thus save yourself time in the long run.  Topics build on themselves so try and stay on top of things and you will be successful!

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