CHEM 2OB3

Mac

Course Overview

Lessons & Practice

I. Welcome

2 min

1. Review: 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. Review: 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. Review: 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. Review: Acid/Base Chemistry & Intro to Organic Reactions

56min

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

4.1.2. Key Definitions in Acids/Bases5 min

4.1.3. Acid/Base Equilibrium Constants2 min

4.1.4. Example: Acid/Base Arrows 3 min

4.2.1. Factors Influencing Acid/Base Strength2 min

4.2.2. Electronegativity1 min

4.2.3. Atom Size2 min

4.2.4. Resonance3 min

4.2.5. Hybridization3 min

4.2.6. Induction3 min

4.2.7. Aromaticity3 min

4.2.8. Example: Acid/Base Strength 3 min

4.2.9. Example: Acid/Base Strength 3 min

4.2.10. Practice: Acid/Base Equilibria 2 min

4.2.11. Practice: Acid/Base Equilibria 2 min

4.3.1. Important pKas You Should Know4 min

4.3.2. Relationship Between pH and pKa2 min

4.3.3. Amino Acids at Different pHs3 min

4.3.4. Practice: Amino Acids in Solution3 min

4.3.5. Practice: Amino Acids in Solution3 min

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

4.3.7. Summary Sheet: pKa's of Common Molecules

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

4.Q. Checkpoint Quiz15 Qns

5. Radical Reactions

30min

5.1.1. Radical Stability4 min

5.1.2. Example: Radical Stability3 min

5.1.3. Example: Radical Stability1 min

5.1.4. Practice: Radical Stability1 min

5.2.1. Radical Reactions: Radical Halogenation7 min

5.2.2. Radical Reactions: Hydrohalogenation with a Peroxide7 min

5.2.3. Practice: Radical Reactions2 min

5.2.4. Practice: Radical Reactions2 min

5.2.5. Practice: Radical Reactions3 min

5.3.1. Summary Sheet: Radical Reactions

5.Q. Checkpoint Quiz7 Qns

6. Alcohols and Ethers

1.2hr

6.I. Chapter Intro

6.1.1. Acid-catalyzed Hydration9 min

6.1.2. Example: Acid-catalyzed Hydration4 min

6.1.3. Example: Acid-catalyzed Hydration 23 min

6.2.1. Hydroboration/Oxidation8 min

6.2.2. Example: Hydroboration 13 min

6.2.3. Example: Hydroboration 22 min

6.3.1. Dihydroxylation5 min

6.3.2. Example: Dihydroxylation3 min

6.4.1. Leaving Group Ability4 min

6.4.2. Example: Alcohol as a Leaving Group2 min

6.5.1. Epoxidation8 min

6.5.2. Example: Epoxidation3 min

6.5.3. Example: Epoxides as Electrophiles8 min

6.6.1. Williamson Ether Synthesis8 min

7. Reduction and Oxidation Reactions

42min

7.1.1. Structure and Reactivity (*coming soon)

7.2.1. Thiols (*coming soon)

7.2.2. Sulfides (*coming soon)

7.3.1. Oxidation to make Aldehydes4 min

7.3.2. Oxidation to make Ketones2 min

7.3.3. Oxidation of Aldehydes3 min

7.3.4. Example: Oxidation Reactions5 min

7.4.1. Reduction using NaBH42 min

7.4.2. Reduction using LiAlH44 min

7.4.3. Example: Reduction Reactions3 min

7.4.4. Example: Reductions Reactions5 min

7.5.1. Hydrogenation6 min

7.5.2. Example: Hydrogenation3 min

7.5.3. Example: Hydrogenation2 min

7.5.4. Example: Hydrogenation1 min

7.5.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

7.6.1. Summary Sheet: Reduction and Oxidation Reactions

7.Q. Checkpoint Quiz7 Qns

8. Review: Nucleophilic Substitutions and Elimination Reactions (in the context of alcohols, ethers and epoxides)

1.4hr

8.1.1. General Terminology4 min

8.1.2. Nucleophiles4 min

8.1.3. Electrophiles2 min

8.1.4. Leaving Groups4 min

8.1.5. Substitution vs. Elimination2 min

8.1.6. Example: Substitution vs. Elimination3 min

8.2.1. Molecularity and Rate57 sec

8.2.2. Structural Requirements1 min

8.2.3. SN1 Mechanism4 min

8.2.4. Practice: Sn1 Reaction1 min

8.3.1. Molecularity and Rate1 min

8.3.2. Structural Requirements2 min

8.3.3. SN2 Mechanism4 min

8.3.4. Practice: Sn2 Reaction1 min

8.4.1. Stereochemistry in Substitution Reactions2 min

8.5.1. Leaving Group Ability4 min

8.5.2. Example: Alcohol as a Leaving Group2 min

8.6.1. Solvent Effects in Substitution Reactions6 min

8.7.1. The Williamson Ether Synthesis (*coming soon)

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

8.8.1. Molecularity and Rate43 sec

8.8.2. Structural Requirements52 sec

8.8.3. E1 Mechanism3 min

8.9.1. Molecularity and Rate45 sec

8.9.2. Structural Requirements2 min

8.9.3. Synthesis of Alkynes1 min

8.9.4. E2 Mechanism3 min

8.10.1. Selectivity in Elimination Reactions - E2 Reactions8 min

8.10.2. Selectivity in Elimination Reactions - E1 Reactions4 min

8.10.3. Example: Selectivity in Elimination Reactions6 min

8.11.1. Favouring Elimination over Subsitution5 min

8.12.1. Summary Sheet: Substitution Reactions

8.12.2. Summary Sheet: Elimination Reactions

8.Q. Checkpoint Quiz13 Qns

8.P.1. Practice: Substitution Question 1

8.P.2. Practice: Substitution Question 2

8.P.3. Practice: Elimination Question 1

8.P.4. Practice: Elimination Question 2

8.P.5. Practice: Elimination Question 3

9. Conjugated Systems

1.6hr

9.I. Conjugated Systems Intro32 sec

9.1.1. Conjugated Systems & Radical Reactions16 min

9.1.2. Addition Reactions on Conjugated Systems7 min

9.2.1. Mechanism and Orbital Description of Diels-Alder Reaction23 min

9.2.2. Stereochemistry of Diels-Alder Reaction10 min

9.2.3. Example: Diels-Alder Reaction12 min

9.2.4. Practice: Diels-Alder Reaction18 min

9.2.5. Practice: Diels-Alder Reaction9 min

9.Q. Quiz: Diels-Alder Reaction3 Qns

10. Aromatic Compounds

48min

10.1.1. Aromaticity13 min

10.1.2. Summary Sheet: Naming Aromatic Rings

10.1.3. Example: Aromaticity5 min

10.1.4. Example: Aromaticity3 min

10.1.5. Practice: Aromaticity2 min

10.3.1. Electrophilic Aromatic Substitution Reactions 8 min

10.3.2. Electrophilic Aromatic Substitution4 min

10.4.1. Considerations for Electrophilic Aromatic Substitutions6 min

10.4.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

10.4.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

10.5.1. Summary Sheet: Aromaticity and Related Reactions

10.5.2. Summary Sheet: Naming Aromatic Rings

10.Q. Checkpoint Quiz4 Qns

11. Electrophilic Addition Reactions to Alkenes/Alkynes

2.3hr

11.1.1. Hydrohalogenation9 min

11.1.2. Example: Hydrohalogenation4 min

11.1.3. Example: Hydrohalogenation4 min

11.2.1. Acid-catalyzed Hydration9 min

11.2.2. Example: Acid-catalyzed Hydration4 min

11.2.3. Example: Acid-catalyzed Hydration 23 min

11.3.1. Hydroboration/Oxidation8 min

11.3.2. Example: Hydroboration 13 min

11.3.3. Example: Hydroboration 22 min

11.4.1. Halogenation13 min

11.4.2. Example: Halogenation 13 min

11.4.3. Example: Halogenation 22 min

11.4.4. Example: Halogenation3 min

11.5.1. Ozonolysis9 min

11.5.2. Example: Ozonolysis 12 min

11.5.3. Example: Ozonolysis4 min

11.6.1. Dihydroxylation5 min

11.6.2. Example: Dihydroxylation3 min

11.7.1. Epoxidation8 min

11.7.2. Example: Epoxidation3 min

11.7.3. Example: Epoxides as Electrophiles8 min

11.8.1. Hydrogenation6 min

11.8.2. Example: Hydrogenation 13 min

11.8.3. Example: Hydrogenation 22 min

11.8.4. Example: Hydrogenation 31 min

11.8.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

11.9.1. Carbocation Rearrangements6 min

11.9.2. Example: Carbocation Rearrangements3 min

11.9.3. Example: Carbocation Rearrangements3 min

11.10.1. Reactivity of Dienes (*coming soon)

11.10.2. 1,2- and 1,4-addition of HX to dienes (*coming soon)

11.12.1. Terpene Biosynthesis2 min

11.12.2. Example: Terpene Biosynthesis 12 min

11.12.3. Example: Terpene Biosynthesis4 min

11.13.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

11.Q. Checkpoint Quiz9 Qns

11.P.1. Practice: Reaction Energy Diagrams

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

1.9hr

12.1.1. Nomenclature and Physical Properties3 min

12.2.1. General Reactivity1 min

12.2.2. General Mechanism at the Carbonyl4 min

12.3.1. The Grignard Reaction5 min

12.3.2. Cyanohydrin Formation3 min

12.3.3. Example: The Grignard Reaction2 min

12.3.4. Practice: The Grignard Reaction5 min

12.4.1. General Reactions with Oxygen Nucleophiles5 min

12.4.2. Hydrate Formation1 min

12.4.3. Acetal Formation2 min

12.4.4. Ketal Formation2 min

12.4.5. Hydrolysis of Acetals and Ketals3 min

12.4.6. General Mechanism with Oxygen Nucleophiles9 min

12.4.7. Stability of Hemiketals and Hemiacetals3 min

12.4.8. Practice: Ketals and Acetals as Protecting Groups2 min

12.4.9. Practice: Ketals and Acetals as Protecting Groups2 min

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

12.4.11. Practice: Mechanism in Acetal and Ketal Formation3 min

12.4.12. Practice: Identifying Acetals/Aldehydes2 min

12.5.1. Synthesis and Hydrolysis of Imines7 min

12.5.2. Enamine Formation2 min

12.5.3. Mechanism of Imiine Formation4 min

12.5.4. Reductive Amination2 min

12.5.5. Practice: Imine Formation2 min

12.6.1. Tautomerization8 min

12.6.2. Enolate Formation3 min

12.6.3. Kinetic vs. Thermodynamic Enolates5 min

12.6.4. The Aldol Reaction3 min

12.6.5. Mechanism of the Aldol Reaction5 min

12.6.6. The Retro-Aldol Reaction1 min

12.6.7. Mixed Aldol Reactions5 min

12.6.8. Example: The Aldol Reaction4 min

12.6.9. Practice: The Aldol Reaction2 min

12.7.1. Study Sheet: Reaction Overview and Key Ideas

12.Q. Checkpoint Quiz4 Qns

13. Carbohydrates

56min

13.1.1. Straight Chain Nomenclature7 min

13.1.2. Cyclization of Monosaccharides5 min

13.1.3. Cyclic Nomenclature6 min

13.1.4. Glycosidic Bonds2 min

13.1.5. Example: Carbohydrate Nomenclature3 min

13.1.6. Example: Carbohydrate Nomenclature (Glycosides)4 min

13.2.1. Converting Fischer Structures4 min

13.2.2. Example: Converting Fischer Structures3 min

13.2.3. Example: Converting Fischer Structures3 min

13.2.4. Practice Question: Converting Fischer Projections2 min

13.3.1. Carbohydrate Reactions: Formation of Glycosidic Bonds4 min

13.3.2. Carbohydrate Reactions: Hydrolysis of Glycosidic Bonds1 min

13.3.3. Carbohydrate Reactions: Reducing Sugars2 min

13.3.4. Practice: Carbohydrates in Solution1 min

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

13.3.6. Example: Identifying Reducing Sugars2 min

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

13.4.1. Carbohydrates

13.Q. Checkpoint Quiz15 Qns

14. Carboxylic Acid Derivatives (Nucleophilic Acyl Substitutions)

1.1hr

14.1.1. Carboxylic Acids2 min

14.1.2. Example: Carboxylic Acids5 min

14.1.3. Example: Carboxylic Acids2 min

14.2.1. Nomenclature and Physical Properties3 min

14.3.1. General Reactivity3 min

14.3.2. General Mechanism at the Carbonyl2 min

14.3.3. Practice: General Reactivity34 sec

14.3.4. Summary Sheet: Carboxylic Acid Reactivity

14.4.1. Acyl Halides3 min

14.4.2. Example: Acyl Halides2 min

14.4.3. Example: Acyl Halides 22 min

14.5.1. Synthesis of Anhydrides

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

14.5.3. Other Syntheses of Esters1 min

14.5.4. Transesterification2 min

14.5.5. Example: Esters and Anhydrides9 min

14.5.6. Example: Esters and Anhydrides 28 min

14.6.1. Formation of Amides from Acid Halides1 min

14.6.2. Example: Amides3 min

14.6.3. Example: Amides2 min

14.6.4. Practice: Peptide Bonds50 sec

14.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

14.7.2. Hydrolysis of Esters and Amides24 sec

14.8.1. Claisen Reactions3 min

14.8.2. Example: Claisen Reactions4 min

14.8.3. Example: Claisen Reactions2 min

14.8.4. Example: Dieckmann Condensation3 min

14.9.1. Nucleophilic Acyl Substitutions

14.Q. Checkpoint Quiz13 Qns

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

15.1.1. Structure of Amino Acids (*coming soon)

15.1.2. pKa of Amino Acids (*coming soon)

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

15.2.1. Lipids (*coming soon)

15.2.2. Sterols (*coming soon)

16. Amines

17min

16.I. Chapter Intro

16.1.1. Synthesis and Hydrolysis of Imines7 min

16.1.2. Enamine Formation2 min

16.1.3. Mechanism of Imiine Formation4 min

16.1.4. Reductive Amination2 min

16.1.5. Practice: Imine Formation2 min

Mock Exams

ME.1. Term Test 2 - Mock Assessment43 Qns

ME.2. Final Examination - Mock Assessment110 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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