This is the third and final in a series of posts answering some frequently asked questions about the third edition of Joel Karty’s Organic Chemistry: Principles and Mechanisms. You can see the previous post in the series here. This section covers questions about using the textbook in alternative orders. If you have any unanswered questions please ask them in the comments below.
With the Karty textbook, can I teach all of carbonyl chemistry in the first semester?
Yes, and here is one way it has been done successfully by our users:
Organic Chemistry I
Chapter 1. Atomic and Molecular Structure
Chapter 2. Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties
Chapter 3. Valence Bond Theory and Molecular Orbital Theory
Chapter 4. Isomerism 1. Conformers and Constitutional Isomers
Chapter 5. Isomerism 2. Chirality, Enantiomers, and Diastereomers
Chapter 6. The Proton Transfer Reaction: And Introduction to Mechanisms, Equilibria, Free Energy Diagrams, and Charge Stability
Chapter 7. An Overview of the Most Common Elementary Steps
Chapter 8. An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and Their Comparisons to SN2 and E2 Reactions
Chapter 9. Competition Among SN2, SN1, E2, and E1 Reactions
Chapter 18. Nucleophilic Addition to Polar p Bonds 1. Reagents That Are Strongly Nucleophilic
- Skip the following sections: 18.6 & 18.7, Wittig reactions and Wittig reagents; 18.10 – 18.12, organic synthesis
Chapter 19. Nucleophilic Addition to Polar p Bonds 1. Reagents That Are Weakly Nucleophilic or Non-nucleophilic, and Acid and Base Catalysis
- Skip the following sections: 19.5, reductive amination; 19.6, the Wolff-Kishner reduction; 19.13, the Robinson annulation; 19.14, organic synthesis
Chapter 22. Nucleophilic Addition-Elimination Reactions 1. Reagents That Are Strongly Nucleophilic
- Skip the following sections: 22.4, Gabriel synthesis; 22.5, haloform reactions; 21.7, specialized reducing agents
Chapter 23. Nucleophilic Addition-Elimination Reactions 2. Reagents That Are Weakly Nucleophilic or Non-Nucleophilic
- Skip the following sections: 23.4, synthesis of acyl halides; 23.5, the Hell-Vollhard-Zelinsky reaction; 23.6, synthesis of sulfonyl chlorides; 23.8, Baeyer-Villiger oxidations; 23.10, organic synthesis
Chapter 29. Biomolecules 1. An Overview of the Four Major Classes of Biomolecules
- Skip the following sections: 29.15 – 29.19, lipids.
Organic Chemistry II
Chapter 10. Organic Synthesis 1. Nucleophilic Substitution and Elimination Reactions and Functional Group Transformations
Chapter 11. Organic Synthesis 2. Reactions That Alter the Carbon Skeleton, and Designing Multistep Syntheses
Chapter 18. Nucleophilic Addition to Polar p Bonds 1. Reagents That Are Strongly Nucleophilic
- Just these sections that were skipped in first semester: 18.6 & 18.7, Wittig reactions and Wittig reagents; 18.10 – 18.12, organic synthesis
Chapter 19. Nucleophilic Addition to Polar p Bonds 1. Reagents That Are Weakly Nucleophilic or Non-nucleophilic, and Acid and Base Catalysis
- Just these sections that were skipped in first semester: 19.5, reductive amination; 19.6, the Wolff-Kishner reduction; 19.13, the Robinson annulation; 19.14, organic synthesis
Chapter 20. Redox Reactions; Organometallic Reagents and Their Reactions
Chapter 21. Organic Synthesis 3. Intermediate Topics in Synthesis Design
Chapter 22. Nucleophilic Addition-Elimination Reactions 1. Reagents That Are Strongly Nucleophilic
- Just these sections that were skipped in first semester: 22.4, Gabriel synthesis; 22.5, haloform reactions; 21.7, specialized reducing agents
Chapter 23. Nucleophilic Addition-Elimination Reactions 2. Reagents That Are Weakly Nucleophilic or Non-Nucleophilic
- Just these sections that were skipped in first semester: 23.4, synthesis of acyl halides; 23.5, the Hell-Vollhard-Zelinsky reaction; 23.6, synthesis of sulfonyl chlorides; 23.8, Baeyer-Villiger oxidations; 23.10, organic synthesis
Chapter 12. Electrophilic Addition to Nonpolar p Bonds 1. Addition of a Brønsted Acid
Chapter 13. Electrophilic Addition to Nonpolar p Bonds 2. Reactions Involving Cyclic Transition States
Chapter 14. Conjugation and Aromaticity
Chapter 15. Structure Determination 1. Mass Spectrometry
Chapter 16. Structure Determination 2. Infrared Spectroscopy and Ultraviolet-Visible Spectroscopy
Chapter 17. Structure Determination 3. Nuclear Magnetic Resonance Spectroscopy
Chapter 24. Aromatic Substitution 1. Electrophilic Aromatic Substitution on Benzene, and Useful Accompanying Reactions
Chapter 25. Aromatic Substitution 2. Reactions of Substituted Benzenes and Other Rings
Chapter 26. The Diels-Alder Reaction, Syn Dihydroxylation, and Oxidative Cleavage
Chapter 27. Reactions Involving Radicals
Chapter 28. Polymers
By organizing the two-semester sequence in the above way, each semester has a distinct theme. First semester focuses on organic structure and reactivity, with emphasis on reactions in which the nucleophile is an electron-rich atom with a lone pair of electrons. Second semester focuses on organic synthesis and spectroscopy, and also introduces reactions in which the nucleophile is a nonpolar p bond, along with cycloaddition and radical reactions.
With the Karty textbook, can I teach alkene/alkyne chemistry in its entirety (including Diels-Alder and oxidative cleavage reactions) in first semester?
Yes, and here is one way it has been done successfully by our users:
Organic Chemistry I
Chapter 1. Atomic and Molecular Structure
Chapter 2. Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties
Chapter 3. Valence Bond Theory and Molecular Orbital Theory
Chapter 4. Isomerism 1. Conformers and Constitutional Isomers
Chapter 5. Isomerism 2. Chirality, Enantiomers, and Diastereomers
Chapter 6. The Proton Transfer Reaction: And Introduction to Mechanisms, Equilibria, Free Energy Diagrams, and Charge Stability
Chapter 7. An Overview of the Most Common Elementary Steps
Chapter 8. An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and Their Comparisons to SN2 and E2 Reactions
Chapter 12. Electrophilic Addition to Nonpolar p Bonds 1. Addition of a Brønsted Acid
Chapter 13. Electrophilic Addition to Nonpolar p Bonds 2. Reactions Involving Cyclic Transition States
- Plus Section 20.3. Catalytic Hydrogenation: A Review of Alkene and Alkyne Reductions, Reductions of Other Functional Groups, and Selectrivity
Chapter 14. Conjugation and Aromaticity
Chapter 26. The Diels-Alder Reaction, Syn Dihydroxylation, and Oxidative Cleavage
Chapter 15. Structure Determination 1. Mass Spectrometry
Chapter 16. Structure Determination 2. Infrared Spectroscopy and Ultraviolet-Visible Spectroscopy
Organic Chemistry II
Chapter 9. Competition Among SN2, SN1, E2, and E1 Reactions
Chapter 10. Organic Synthesis 1. Nucleophilic Substitution and Elimination Reactions and Functional Group Transformations
Chapter 11. Organic Synthesis 2. Reactions That Alter the Carbon Skeleton, and Designing Multistep Syntheses
Chapter 17. Structure Determination 3. Nuclear Magnetic Resonance Spectroscopy
Chapter 18. Nucleophilic Addition to Polar p Bonds 1. Reagents That Are Strongly Nucleophilic
Chapter 19. Nucleophilic Addition to Polar p Bonds 1. Reagents That Are Weakly Nucleophilic or Non-nucleophilic, and Acid and Base Catalysis
Chapter 20. Redox Reactions; Organometallic Reagents and Their Reactions
Chapter 21. Organic Synthesis 3. Intermediate Topics in Synthesis Design
Chapter 22. Nucleophilic Addition-Elimination Reactions 1. Reagents That Are Strongly Nucleophilic
Chapter 23. Nucleophilic Addition-Elimination Reactions 2. Reagents That Are Weakly Nucleophilic or Non-Nucleophilic
Chapter 24. Aromatic Substitution 1. Electrophilic Aromatic Substitution on Benzene, and Useful Accompanying Reactions
Chapter 25. Aromatic Substitution 2. Reactions of Substituted Benzenes and Other Rings
Chapter 27. Reactions Involving Radicals
Chapter 28. Polymers
One caveat to rearranging topics in this order is the potential risk for students to memorize aspects of Chapter 26 reactions. Also, in first semester, it might be tempting to jump straight from Chapter 7 to Chapter 12. It can be done effectively, but I would caution against doing so, because Chapter 8 covers important concepts to help students work comfortably with multistep mechanism, including stereochemistry, how to reasonably incorporate proton transfer steps into multistep mechanisms, and how to deal with resonance delocalized intermediates.
-Joel Karty, Elon University
Feel free to share your thoughts in the “Comments” section below!
