CHEM-2535

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)

1.5hr

2.1.1. Introduction to Hydrocarbons7 min

2.1.2. Cyclic Hydrocarbons56 sec

2.1.3. Hydrocarbons2 min

2.2.1. Summary Sheet: Common Organic Functional Groups

2.2.2. Example: Functional Groups 2 min

2.3.1. What is Organic Chemistry?

2.3.2. 5 Ways to Represent Alkane Structures5 min

2.3.3. Line Bond Drawing6 min

2.3.4. A Closer Look at Line Drawings

2.3.5. Example

2.4.1. Drawing Organic Compouds in 2D2 min

2.4.2. Example: 2-D Notation2 min

2.4.3. Example: 2-D Notation1 min

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

2.4.5. Summary Sheet: Condensed Formula

2.5.1. Drawing Organic Compounds in 3D5 min

2.5.2. Example: 3-D Notation2 min

2.5.3. Example: 3-D Notation2 min

2.5.4. Summary Sheet: Drawing in 3-Dimensions

2.6.1. Chair Conformations4 min

2.6.2. Example: Chair Conformations60 sec

2.6.3. Example: Chair Conformations1 min

2.6.4. Practice: Chair Conformations2 min

2.7.1. IUPAC Systematic Naming Theory15 min

2.7.2. Example: Converting Names to Structures2 min

2.7.3. Example: IUPAC Systematic Naming2 min

2.7.4. Example: IUPAC Systematic Naming2 min

2.7.5. Practice: IUPAC Systematic Naming2 min

2.7.6. Practice: IUPAC Systematic Naming2 min

2.7.7. Summary Sheet: IUPAC Naming

2.8.1. Functional Groups12 min

2.8.2. Steps to Naming Complex Organic Molecules4 min

2.8.3. Naming Organic Molecules with Odd Functional Groups2 min

2.8.4. Example

2.8.5. Practice

2.8.6. Practice

2.8.7. Functional Group Parent Names Cheatsheet

2.Q. Checkpoint Quiz15 Qns

3. Acid/Base Chemistry & Intro to Organic Reactions

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

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. 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. Nucleophilic Substitutions and Elimination Reactions

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. Electrophilic Addition Reactions to Alkenes/Alkynes

2.3hr

7.1.1. Hydrohalogenation9 min

7.1.2. Example: Hydrohalogenation4 min

7.1.3. Example: Hydrohalogenation4 min

7.2.1. Acid-catalyzed Hydration9 min

7.2.2. Example: Acid-catalyzed Hydration4 min

7.2.3. Example: Acid-catalyzed Hydration 23 min

7.3.1. Hydroboration/Oxidation8 min

7.3.2. Example: Hydroboration 13 min

7.3.3. Example: Hydroboration 22 min

7.4.1. Halogenation13 min

7.4.2. Example: Halogenation 13 min

7.4.3. Example: Halogenation 22 min

7.4.4. Example: Halogenation3 min

7.5.1. Ozonolysis9 min

7.5.2. Example: Ozonolysis 12 min

7.5.3. Example: Ozonolysis4 min

7.6.1. Dihydroxylation5 min

7.6.2. Example: Dihydroxylation3 min

7.7.1. Epoxidation8 min

7.7.2. Example: Epoxidation3 min

7.7.3. Example: Epoxides as Electrophiles8 min

7.8.1. Hydrogenation6 min

7.8.2. Example: Hydrogenation 13 min

7.8.3. Example: Hydrogenation 22 min

7.8.4. Example: Hydrogenation 31 min

7.8.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

7.9.1. Carbocation Rearrangements6 min

7.9.2. Example: Carbocation Rearrangements3 min

7.9.3. Example: Carbocation Rearrangements3 min

7.10.1. Reactivity of Dienes (*coming soon)

7.10.2. 1,2- and 1,4-addition of HX to dienes (*coming soon)

7.12.1. Terpene Biosynthesis2 min

7.12.2. Example: Terpene Biosynthesis 12 min

7.12.3. Example: Terpene Biosynthesis4 min

7.13.1. Summary Sheet: Electrophilic Addition to Alkenes/Alkynes

7.Q. Checkpoint Quiz9 Qns

7.P.1. Practice: Reaction Energy Diagrams

8. Reduction and Oxidation Reactions

42min

8.1.1. Structure and Reactivity (*coming soon)

8.2.1. Thiols (*coming soon)

8.2.2. Sulfides (*coming soon)

8.3.1. Oxidation to make Aldehydes4 min

8.3.2. Oxidation to make Ketones2 min

8.3.3. Oxidation of Aldehydes3 min

8.3.4. Example: Oxidation Reactions5 min

8.4.1. Reduction using NaBH42 min

8.4.2. Reduction using LiAlH44 min

8.4.3. Example: Reduction Reactions3 min

8.4.4. Example: Reductions Reactions5 min

8.5.1. Hydrogenation6 min

8.5.2. Example: Hydrogenation3 min

8.5.3. Example: Hydrogenation2 min

8.5.4. Example: Hydrogenation1 min

8.5.5. Example: Hydrogenation with Isotopes of Hydrogen2 min

8.6.1. Summary Sheet: Reduction and Oxidation Reactions

8.Q. Checkpoint Quiz7 Qns

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

1.9hr

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.Q. Checkpoint Quiz4 Qns

10. Carboxylic Acid Derivatives (Nucleophilic Acyl Substitutions)

1.1hr

10.1.1. Carboxylic Acids2 min

10.1.2. Example: Carboxylic Acids5 min

10.1.3. Example: Carboxylic Acids2 min

10.2.1. Nomenclature and Physical Properties3 min

10.3.1. General Reactivity3 min

10.3.2. General Mechanism at the Carbonyl2 min

10.3.3. Practice: General Reactivity34 sec

10.3.4. Summary Sheet: Carboxylic Acid Reactivity

10.4.1. Acyl Halides3 min

10.4.2. Example: Acyl Halides2 min

10.4.3. Example: Acyl Halides 22 min

10.5.1. Synthesis of Anhydrides

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

10.5.3. Other Syntheses of Esters1 min

10.5.4. Transesterification2 min

10.5.5. Example: Esters and Anhydrides9 min

10.5.6. Example: Esters and Anhydrides 28 min

10.6.1. Formation of Amides from Acid Halides1 min

10.6.2. Example: Amides3 min

10.6.3. Example: Amides2 min

10.6.4. Practice: Peptide Bonds50 sec

10.7.1. Hydrolysis of Acid Halides and Anhydrides38 sec

10.7.2. Hydrolysis of Esters and Amides24 sec

10.8.1. Claisen Reactions3 min

10.8.2. Example: Claisen Reactions4 min

10.8.3. Example: Claisen Reactions2 min

10.8.4. Example: Dieckmann Condensation3 min

10.9.1. Nucleophilic Acyl Substitutions

10.Q. Checkpoint Quiz13 Qns

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

1.9hr

11.1.1. Hydrogen Deficiency Index4 min

11.2.1. Infrared Spectroscopy12 min

11.2.2. Example: IR Spectroscopy2 min

11.2.3. Example: IR Spectroscopy52 sec

11.2.4. Practice Question: IR Spectroscopy1 min

11.2.5. Practice Question: IR Spectroscopy 21 min

11.3.1. Mass Spectrometry9 min

11.3.2. Example: Mass Spectrometry4 min

11.3.3. Example: Mass Spectrometry2 min

11.3.4. Example: Mass Spectrometry2 min

11.4.1. UV-vis Spectroscopy5 min

11.4.2. UV-vis Study Sheet

11.5.1. NMR Theory6 min

11.5.2. Example: Intro to NMR2 min

11.5.3. Example: Intro to NMR2 min

11.6.1. Hydrogen (1H NMR)20 min

11.6.2. Example: 1H NMR3 min

11.6.3. Example: 1H NMR6 min

11.6.4. Practice: 1H NMR 3 min

11.6.5. Practice Question: 1H NMR2 min

11.6.6. Practice Question: 1H NMR1 min

11.6.7. Practice Question4 min

11.7.1. Carbon (13C) NMR8 min

11.7.2. Example: 13C NMR3 min

11.7.3. Example: 13C NMR4 min

11.7.4. Practice: 13C NMR3 min

11.7.5. Example: 13C NMR3 min

11.8.1. Structure Elucidation

11.Q. Checkpoint Quiz3 Qns

11.P.1. Practice: Structure Elucidation 1

11.P.2. Practice: Structure Elucidation 2

11.P.3. Practice: Structure Elucidation 3

12. Aromaticity (Arenes)

48min

12.1.1. Aromaticity13 min

12.1.2. Summary Sheet: Naming Aromatic Rings

12.1.3. Example: Aromaticity5 min

12.1.4. Example: Aromaticity3 min

12.1.5. Practice: Aromaticity2 min

12.3.1. Electrophilic Aromatic Substitution Reactions 8 min

12.3.2. Electrophilic Aromatic Substitution4 min

12.4.1. Considerations for Electrophilic Aromatic Substitutions6 min

12.4.2. Example: Directing Groups in Electrophilic Aromatic Substitution2 min

12.4.3. Example: Directing Groups in Electrophilic Aromatic Substitution4 min

12.5.1. Summary Sheet: Aromaticity and Related Reactions

12.5.2. Summary Sheet: Naming Aromatic Rings

12.Q. Checkpoint Quiz4 Qns

13. The Diels-Alder Reactions & Dienes

34min

13.1.1. The Diels-Alder Reaction4 min

13.2.1. Stereochemistry of Diels-Alder Reaction12 min

13.4.1. Diels-Alder Reaction

13.4.2. Practice: Diels-Alder Reaction18 min

13.4.3. Rate of Reaction

13.4.4. New Practice Question

Mock Exams

ME.1. Test 2 - Mock Assessment24 Qns

ME.2. Final Exam - Mock Assessment22 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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