CHEM 2E03

Mac

Course Overview

Lessons & Practice

I. Welcome

2 min

1. Review of General Chemistry

1.5hr

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. VSEPR Theory5 min

1.5.2. Example: VSEPR2 min

1.5.3. Example: VSEPR3 min

1.5.4. Practice: VSEPR4 min

1.6.1. Polar Bonds6 min

1.6.2. Example: Polar Bonds3 min

1.6.3. Example: Polar Bonds 2 min

1.6.4. Practice: Polar Bonds 50 sec

1.7.1. Intermolecular Forces4 min

1.7.2. Melting and Boiling Point Comparison4 min

1.7.3. Example: Intermolecular Forces3 min

1.7.4. Example: Intermolecular Forces2 min

1.7.5. Practice: Intermolecular Forces1 min

1.8.1. Drawing Organic Compouds in 2D2 min

1.8.2. Example: 2-D Notation2 min

1.8.3. Example: 2-D Notation1 min

1.8.4. Summary Sheet: Representing Molecules in Different 2D Notation

1.8.5. Summary Sheet: Condensed Formula

1.9.1. Summary Sheet: The Basics

2. Molecular Representations

12min

2.1.1. Bonding in Delocalized Systems3 min

2.1.2. Example: Resonance Structures6 min

2.2.1. Summary Sheet: Common Organic Functional Groups

2.2.2. Example: Functional Groups 2 min

3. Acids and Bases

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

4. Alkanes and Cycloalkanes

45min

4.1.1. Summary Sheet: Common Organic Functional Groups

4.1.2. Example: Functional Groups 2 min

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

4.3.1. Chair Conformations4 min

4.3.2. Example: Chair Conformations60 sec

4.3.3. Example: Chair Conformations1 min

4.3.4. Practice: Chair Conformations2 min

4.4.1. IUPAC Systematic Naming Theory15 min

4.4.2. Example: Converting Names to Structures2 min

4.4.3. Example: IUPAC Systematic Naming2 min

4.4.4. Example: IUPAC Systematic Naming2 min

4.4.5. Practice: IUPAC Systematic Naming2 min

4.4.6. Practice: IUPAC Systematic Naming2 min

4.4.7. Summary Sheet: IUPAC Naming

5. Stereoisomerism

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. Mass Spectrometry

22min

6.1.1. Hydrogen Deficiency Index4 min

6.2.1. Mass Spectrometry9 min

6.2.2. Example: Mass Spectrometry4 min

6.2.3. Example: Mass Spectrometry2 min

6.2.4. Example: Mass Spectrometry2 min

7. Addition Reactions of Alkenes

2.2hr

7.1.1. Carbocation Rearrangements6 min

7.1.2. Example: Carbocation Rearrangements3 min

7.1.3. Example: Carbocation Rearrangements3 min

7.2.1. Hydrohalogenation9 min

7.2.2. Example: Hydrohalogenation4 min

7.2.3. Example: Hydrohalogenation4 min

7.3.1. Acid-catalyzed Hydration9 min

7.3.2. Example: Acid-catalyzed Hydration4 min

7.3.3. Example: Acid-catalyzed Hydration 23 min

7.4.1. Hydroboration/Oxidation8 min

7.4.2. Example: Hydroboration 13 min

7.4.3. Example: Hydroboration 22 min

7.5.1. Halogenation13 min

7.5.2. Example: Halogenation 13 min

7.5.3. Example: Halogenation 22 min

7.5.4. Example: Halogenation3 min

7.6.1. Ozonolysis9 min

7.6.2. Example: Ozonolysis 12 min

7.6.3. Example: Ozonolysis4 min

7.7.1. Dihydroxylation5 min

7.7.2. Example: Dihydroxylation3 min

7.8.1. Epoxidation8 min

7.8.2. Example: Epoxidation3 min

7.8.3. Example: Epoxides as Electrophiles8 min

7.9.1. Hydrogenation6 min

7.9.2. Example: Hydrogenation 13 min

7.9.3. Example: Hydrogenation 22 min

7.9.4. Example: Hydrogenation 31 min

7.9.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

7.10.1. Halohydrin Formation

7.11.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

7.P.1. Practice: Reaction Energy Diagrams

8. Reactions of Alkynes

8.1.1. Preparation of Alkynes from Vicinal Dihalides

8.1.2. Preparation of Alkynes from Geminal Dihalides

8.1.3. C-C Bond Formation Using Terminal Alkynes

8.2.1. Hydrogenation of Alkynes (Review)

8.2.2. Hydrohalogenation of Alkynes

8.2.3. Hydrohalogenation of Alkynes with HBr and Peroxides

8.2.4. Mercury-Catalyzed Hydration of Alkynes

8.2.5. Hydroboration-Oxidation of Alkynes

8.2.6. Halogenation of Alkynes

8.2.7. Ozonolysis of Alkynes

9. Substitution Reactions

48min

9.1.1. General Terminology4 min

9.1.2. Nucleophiles4 min

9.1.3. Electrophiles2 min

9.1.4. Leaving Groups4 min

9.1.5. Substitution vs. Elimination2 min

9.1.6. Example: Substitution vs. Elimination3 min

9.2.1. Molecularity and Rate57 sec

9.2.2. Structural Requirements1 min

9.2.3. SN1 Mechanism4 min

9.2.4. Practice: Sn1 Reaction1 min

9.3.1. SN1 Reactions Theory: Carbocation Stability

9.3.2. Carbocation Stability

9.4.1. Molecularity and Rate1 min

9.4.2. Structural Requirements2 min

9.4.3. SN2 Mechanism4 min

9.4.4. Practice: Sn2 Reaction1 min

9.5.1. Stereochemistry in Substitution Reactions2 min

9.6.1. Leaving Group Ability4 min

9.6.2. Example: Alcohol as a Leaving Group2 min

9.7.1. Solvent Effects in Substitution Reactions6 min

10. Epoxides

21min

10.1.1. Overview of Ethers

10.1.2. Williamson Ether Synthesis8 min

10.1.3. Epoxidation (Review)

10.1.4. Stereochemistry of Epoxide Formation and Opening13 min

11. Elimination Reactions

34min

11.1.1. Molecularity and Rate43 sec

11.1.2. Structural Requirements52 sec

11.1.3. E1 Mechanism3 min

11.2.1. Molecularity and Rate45 sec

11.2.2. Structural Requirements2 min

11.2.3. Synthesis of Alkynes1 min

11.2.4. E2 Mechanism3 min

11.3.1. Selectivity in Elimination Reactions - E2 Reactions8 min

11.3.2. Selectivity in Elimination Reactions - E1 Reactions4 min

11.3.3. Example: Selectivity in Elimination Reactions6 min

11.4.1. Favouring Elimination over Subsitution5 min

11.5.1. Summary Sheet: Substitution Reactions

11.5.2. Summary Sheet: Elimination Reactions

11.P.1. Practice: Substitution Question 2

11.P.2. Practice: Elimination Question 1

11.P.3. Practice: Elimination Question 2

12. IR Spectroscopy

39min

12.1.1. Hydrogen Deficiency Index4 min

12.2.1. Infrared Spectroscopy12 min

12.2.2. Example: IR Spectroscopy2 min

12.2.3. Example: IR Spectroscopy52 sec

12.2.4. Practice Question: IR Spectroscopy1 min

12.2.5. Practice Question: IR Spectroscopy 21 min

12.3.1. Structure Elucidation

12.4.1. Infrared Spectroscopy12 min

12.4.2. Example: IR Spectroscopy2 min

12.4.3. Example: IR Spectroscopy52 sec

12.4.4. Practice Question: IR Spectroscopy1 min

12.4.5. Practice Question: IR Spectroscopy 21 min

12.4.6. Practice: Structure Elucidation 1

13. NMR Spectroscopy

1.2hr

13.1.1. NMR Theory6 min

13.1.2. Example: Intro to NMR2 min

13.1.3. Example: Intro to NMR2 min

13.2.1. Hydrogen (1H NMR)20 min

13.2.2. Example: 1H NMR3 min

13.2.3. Example: 1H NMR6 min

13.2.4. Practice: 1H NMR 3 min

13.2.5. Practice Question: 1H NMR2 min

13.2.6. Practice Question: 1H NMR1 min

13.2.7. Practice Question4 min

13.3.1. Carbon (13C) NMR8 min

13.3.2. Example: 13C NMR3 min

13.3.3. Example: 13C NMR4 min

13.3.4. Practice: 13C NMR3 min

13.3.5. Example: 13C NMR3 min

13.4.1. Structure Elucidation

13.P.1. Practice: Structure Elucidation 2

13.P.2. Practice: Structure Elucidation 3

14. Alcohols

14.1.1. Physical Properties and Naming

14.2.1. Alcohol Reactivity

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

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

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

14.3.4. Electrophilic Addition to Alkenes: Dihydroxylation (Review)

14.3.5. Oxymercuration Reactions (Review)

14.4.1. Halogenation of Alcohols

14.4.2. Elimination of Alcohols to Alkenes

15. Aldehydes and Ketones

2.3hr

15.1.1. Nomenclature and Physical Properties3 min

15.2.1. Oxidation to make Aldehydes4 min

15.2.2. Oxidation to make Ketones2 min

15.2.3. Oxidation of Aldehydes3 min

15.2.4. Example: Oxidation Reactions5 min

15.3.1. Reduction using NaBH42 min

15.3.2. Reduction using LiAlH44 min

15.3.3. Example: Reduction Reactions3 min

15.3.4. Example: Reductions Reactions5 min

15.4.1. Summary Sheet: Reduction and Oxidation Reactions

15.5.1. General Reactivity1 min

15.5.2. General Mechanism at the Carbonyl4 min

15.6.1. The Grignard Reaction5 min

15.6.2. Cyanohydrin Formation3 min

15.6.3. Example: The Grignard Reaction2 min

15.6.4. Practice: The Grignard Reaction5 min

15.7.1. General Reactions with Oxygen Nucleophiles5 min

15.7.2. Hydrate Formation1 min

15.7.3. Acetal Formation2 min

15.7.4. Ketal Formation2 min

15.7.5. Hydrolysis of Acetals and Ketals3 min

15.7.6. General Mechanism with Oxygen Nucleophiles9 min

15.7.7. Stability of Hemiketals and Hemiacetals3 min

15.7.8. Practice: Ketals and Acetals as Protecting Groups2 min

15.7.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

15.7.11. Practice: Mechanism in Acetal and Ketal Formation3 min

15.7.12. Practice: Reagents in Acetal and Ketal Chemistry

15.7.13. Practice: Identifying Acetals/Aldehydes2 min

15.8.1. Synthesis and Hydrolysis of Imines7 min

15.8.2. Enamine Formation2 min

15.8.3. Mechanism of Imiine Formation4 min

15.8.4. Reductive Amination2 min

15.8.5. Practice: Imine Formation2 min

15.9.1. Tautomerization8 min

15.9.2. Enolate Formation3 min

15.9.3. Kinetic vs. Thermodynamic Enolates5 min

15.9.4. The Aldol Reaction3 min

15.9.5. Mechanism of the Aldol Reaction5 min

15.9.6. The Retro-Aldol Reaction1 min

15.9.7. Mixed Aldol Reactions5 min

15.9.8. Example: The Aldol Reaction4 min

15.9.9. Practice: The Aldol Reaction2 min

15.10.1. Study Sheet: Reaction Overview and Key Ideas

16. Carboxylic Acids

1.1hr

16.1.1. Carboxylic Acids2 min

16.1.2. Example: Carboxylic Acids5 min

16.1.3. Example: Carboxylic Acids2 min

16.2.1. Nomenclature and Physical Properties3 min

16.3.1. General Reactivity3 min

16.3.2. General Mechanism at the Carbonyl2 min

16.3.3. Practice: General Reactivity34 sec

16.3.4. Summary Sheet: Carboxylic Acid Reactivity

16.4.1. Acyl Halides3 min

16.4.2. Example: Acyl Halides2 min

16.4.3. Example: Acyl Halides 22 min

16.5.1. Synthesis of Anhydrides

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

16.5.3. Other Syntheses of Esters1 min

16.5.4. Transesterification2 min

16.5.5. Example: Esters and Anhydrides9 min

16.5.6. Example: Esters and Anhydrides 28 min

16.6.1. Formation of Amides from Acid Halides1 min

16.6.2. Example: Amides3 min

16.6.3. Example: Amides2 min

16.6.4. Practice: Peptide Bonds50 sec

16.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

16.7.2. Hydrolysis of Esters and Amides24 sec

16.8.1. Claisen Reactions3 min

16.8.2. Example: Claisen Reactions4 min

16.8.3. Example: Claisen Reactions2 min

16.8.4. Example: Dieckmann Condensation3 min

16.9.1. Nucleophilic Acyl Substitutions

Mock Exams

ME.1. Midterm Exam 1 - Mock Assessment37 Qns

ME.2. Midterm Exam 2 - Mock Assessment27 Qns

ME.3. Final Exam - Mock Assessment90 Qns

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AI Tutor answered

Scarlet K

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

Wize AI Tutor

The main idea is that hydrogens are equivalent if they are in the exact same chemical environment, so they give one signal. A few ways to check:

Look for symmetry first. Find any mirror plane or rotation that swaps parts of the molecule. Hydrogens that get swapped are equivalent. For example, diethyl ether (CH₃CH₂OCH₂CH₃) has only 2 signals since both ethyl groups are identical.
Use the replacement test. Mentally replace one H with a different atom (say Cl), then do the same for the other H. If you get the same compound (or a pair of enantiomers), the H's are equivalent. If you get diastereomers, they are not.
CH₃ hydrogens are always equivalent to each other because of free rotation around the single bond.
CH₂ hydrogens are usually equivalent, except when the molecule has a chiral centre nearby, or in rings and alkenes where the two H's point toward different groups.
Alkenes: on a =CH₂, the two H's are only equivalent if the other carbon has two identical groups. Otherwise one H is cis to one group and the other H is cis to a different group.
Benzene rings: check the substitution pattern. A para-disubstituted ring with two different groups gives 2 aromatic signals, while a monosubstituted ring usually has 3 sets (ortho, meta, para).

A good habit is to label each unique type of H with a letter (a, b, c…) as you go, so you don't double count.

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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