Organic Chemistry 2nd edition

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Thomas N. Sorrell
Publisher: University Science Books

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  • Chapter T: WebAssign Answer Templates and Tutorials
    • T: WebAssign Answer Templates and Tutorials (15)

  • Chapter 1: The Structures of Organic Molecules
    • 1.1: Structural Components of Organic Molecules (9)
    • 1.2: Structural Formulas and Condensed Structures (4)
    • 1.3: Systematic Nomenclature: IUPAC Names (1)
    • 1.4: Constitutional Isomers and Hydrocarbon Substituents (3)
    • 1.5: Naming Organic Compounds (10)

  • Chapter 2: Bonding in Organic Molecules
    • 2.1: Lewis Structures (5)
    • 2.2: Bond Properties
    • 2.3: Resonance Structures (1)
    • 2.4: The Formation of Bonds
    • 2.5: Hybrid Orbitals and Shapes of Molecules (1)
    • 2.6: Bonds with Heteroatoms (1)
    • 2.7: Delocalized π Electron Systems
    • 2.8: Noncovalent Interactions (9)

  • Chapter 3: The Conformations of Organic Molecules
    • 3.1: Conformations of Acyclic Compounds (7)
    • 3.2: Conformations of Cyclic Compounds
    • 3.3: Conformations of Substituted Cyclohexanes (10)
    • 3.4: Conformations of Other Cyclic Compounds (1)

  • Chapter 4: The Stereochemistry of Organic Molecules
    • 4.1: Geometric Isomers of Alkenes (5)
    • 4.2: Chirality and Enantiomers (7)
    • 4.3: Diastereomers (6)
    • 4.4: Fischer Projections (6)
    • 4.5: Reaction Stereochemistry: A Preview

  • Chapter 5: Chemical Reactions and Mechanisms
    • 5.1: General Aspects of Reactions
    • 5.2: Acid–Base Reactions (15)
    • 5.3: Reaction Mechanisms (12)
    • 5.4: Reaction Coordinate Diagrams (6)
    • 5.5: Reactions in Biological Systems

  • Chapter 6: Substitution Reactions of Alkyl Halides
    • 6.1: Fundamental Aspects of Substitution Reactions
    • 6.2: The SN1 Reaction of Alkyl Halides (15)
    • 6.3: The SN2 Reaction of Alkyl Halides (9)
    • 6.4: A Comparison of the SN1 and SN2 Mechanisms (2)

  • Chapter 7: Substitution Reactions of Alcohols and Related Compounds
    • 7.1: Substitution Reactions of Alcohols (2)
    • 7.2: Substitution Reactions of Ethers and Epoxides (9)
    • 7.3: Substitution Reactions of Thiols and Thioethers
    • 7.4: Substitution Reactions in Biochemical Systems

  • Chapter 8: Elimination Reactions of Alkyl Halides, Alcohols, and Related Compounds
    • 8.1: The E1 Reaction (2)
    • 8.2: The E2 Reaction (15)
    • 8.3: Substitution Versus Elimination (8)
    • 8.4: Elimination Reactions in Biology

  • Chapter 9: Addition Reactions of Alkenes and Alkynes
    • 9.1: Electrophilic Addition Reactions of Alkenes (14)
    • 9.2: Electrophilic Addition Reactions of Alkynes (2)
    • 9.3: The Formation of Carbon–Carbon Bonds
    • 9.4: Hydroboration Reactions of π Bonds (2)
    • 9.5: The Addition of Carbenes to π Bonds (4)

  • Chapter 10: Addition Reactions of Conjugated Dienes
    • 10.1: The Structures of Dienes
    • 10.2: Bonding in Conjugated Dienes (1)
    • 10.3: Electrophilic Addition to Conjugated Dienes (1)
    • 10.4: The Diels–Alder Reaction (15)

  • Chapter 11: Oxidation and Reduction Reactions
    • 11.1: Oxidation States in Organic Molecules (1)
    • 11.2: Hydrogenation Reactions (10)
    • 11.3: Oxidation Reactions of Alkenes (7)
    • 11.4: Oxidation Reactions of Alcohols
    • 11.5: Oxidation Reactions of Amines

  • Chapter 12: Free Radical Reactions
    • 12.1: Free Radical Halogenation Reactions (17)
    • 12.2: Reduction via Radical Intermediates (5)
    • 12.3: Free Radical Addition Reactions (4)
    • 12.4: Oxidation via Radical Intermediates

  • Chapter 13: Proton and Carbon NMR Spectroscopy
    • 13.1: Chemical Shifts and Proton Equivalence (1)
    • 13.2: Spin Coupling in Simple Systems (1)
    • 13.3: Interpreting and Predicting 1H NMR Spectra (7)
    • 13.4: Spin Coupling in More Complex Systems
    • 13.5: Carbon NMR Spectra
    • 13.6: Interpreting 13C NMR Spectra (1)

  • Chapter 14: Determining the Structures of Organic Molecules
    • 14.1: Analytical Data in Structure Determinations (4)
    • 14.2: Mass Spectrometry (6)
    • 14.3: Infrared Spectroscopy (6)
    • 14.4: Combined Structure Determination Exercises (2)

  • Chapter 15: Organometallic Reagents and Chemical Synthesis
    • 15.1: Carbon–Carbon Bond Formation
    • 15.2: Organomagnesium and Lithium Compounds (22)
    • 15.3: Transition Metal Organometallic Compounds (9)
    • 15.4: Retrosynthesis (2)
    • 15.5: Selectivity Criteria in Synthesis (2)

  • Chapter 16: Asymmetric Reactions and Synthesis
    • 16.1: Chiral Compounds
    • 16.2: Enantiomeric Resolution (1)
    • 16.3: Asymmetric Synthesis (1)
    • 16.4: Enantioselective Addition Reactions
    • 16.5: Synthetic Design of Chiral Molecules

  • Chapter 17: The Chemistry of Benzene and Its Derivatives
    • 17.1: Structural Aspects of Aromatic Molecules (15)
    • 17.2: Electrophilic Substitution Reactions of Benzene (10)
    • 17.3: Electrophilic Substitution Reactions of Benzene Derivatives (9)
    • 17.4: Other Reactions of Benzene and Its Derivatives (21)

  • Chapter 18: Nucleophilic Addition Reactions of Aldehydes and Ketones
    • 18.1: General Aspects of Nucleophilic Addition Reactions
    • 18.2: Nucleophilic Addition Reactions (5)
    • 18.3: Reduction Reactions of Aldehydes and Ketones (5)
    • 18.4: Oxidation Reactions of Aldehydes and Ketones (6)

  • Chapter 19: Addition–Substitution Reactions of Aldehydes and Ketones: Carbohydrate Chemistry
    • 19.1: Hemiacetals and Acetals (4)
    • 19.2: Acetals as Protecting Groups (3)
    • 19.3: Carbohydrates (9)
    • 19.4: Glycosides
    • 19.5: Oxidation and Reduction Reactions of Carbohydrates

  • Chapter 20: Addition–Elimination Reactions of Aldehydes and Ketones
    • 20.1: Compounds with Carbon–Nitrogen Double Bonds
    • 20.2: Imine Chemistry and Biochemistry (3)
    • 20.3: Enamines (2)
    • 20.4: Ylides (4)

  • Chapter 21: Addition–Elimination Reactions of Carboxylic Acids and Derivatives
    • 21.1: General Aspects of Structure and Reactivity
    • 21.2: Reactions of Carboxylic Acids (3)
    • 21.3: The Chemistry of Acid Chlorides, Thioesters, and Anhydrides (3)
    • 21.4: The Chemistry of Esters (9)
    • 21.5: The Chemistry of Amides (5)
    • 21.6: The Chemistry of Nitriles (4)
    • 21.7: Reactions with Organometallic Compounds (2)
    • 21.8: Reduction Reactions of Carboxylic Acids and Derivatives (3)

  • Chapter 22: The Acid–Base Chemistry of Carbonyl Compounds
    • 22.1: Acidity of Carbonyl Compounds
    • 22.2: Enols and Enolate Ions (4)
    • 22.3: Reactions of Enolate Ions (3)
    • 22.4: Dicarbonyl Compounds (5)
    • 22.5: Reactions of Amide and Imide Ions (1)

  • Chapter 23: The Nucleophilic Addition Reactions of Enolate Ions
    • 23.1: The Aldol Reaction (2)
    • 23.2: Crossed-Aldol Reactions (8)
    • 23.3: The Claisen Condensation (4)
    • 23.4: Crossed-Claisen Condensations (2)

  • Chapter 24: Conjugate Addition Reactions of Unsaturated Carbonyl Compounds
    • 24.1: α,β-Unsaturated Carbonyl Compounds
    • 24.2: Conjugate Addition Reactions (1)
    • 24.3: Conjugate Addition Reactions of Carbanions (2)
    • 24.4: Reduction Reactions

  • Chapter 25: The Chemistry of Polycyclic and Heterocyclic Arenes
    • 25.1: Polycyclic Aromatic Compounds
    • 25.2: Pyridine and Related Heterocycles
    • 25.3: Pyrrole and Related Heterocycles
    • 25.4: Azoles (1)

  • Chapter 26: Polymers and Polymerization
    • 26.1: Polymers and Their Properties
    • 26.2: Chain-Growth Polymerization (1)
    • 26.3: Step-Growth Polymerization (6)
    • 26.4: Modification of Polymers (1)

  • Chapter 27: Amino Acids, Peptides, and Proteins
    • 27.1: Amino Acids (3)
    • 27.2: Chemical Synthesis of Amino Acids (1)
    • 27.3: Asymmetric Synthesis of Amino Acids
    • 27.4: Peptide Synthesis and Analysis (7)
    • 27.5: Protein Structures (1)

  • Chapter 28: Nucleic Acids and Molecular Recognition
    • 28.1: Nucleosides and Nucleotides (3)
    • 28.2: Nucleic Acid Structures (2)
    • 28.3: Molecular Recognition
    • 28.4: Crown Ethers and Cryptands
    • 28.5: Cavity-Containing Molecules
    • 28.6: Recognition Using Hydrogen Bonds

  • Chapter X: Extra Questions: Multistep Synthesis
    • X: Extra Questions: Multistep Synthesis (7)


Organic Chemistry, 2nd edition, by Thomas N. Sorrell maintains all the innovative features of the first edition and focuses on the points of reactivities, allowing students to approach more and more complex molecules with enhanced understanding. The WebAssign component for this title links each question to the eBook and utilizes chemPad and Marvin JS for grading chemical notation and chemical drawings, respectively.

Question Availability Color Key
BLACK questions are available now
GRAY questions are under development


Group Quantity Questions
Chapter T: WebAssign Answer Templates and Tutorials
T.template 12 complete.mrv condensed.mrv lewis.mrv mechanism.mrv mechanism_adv.mrv multistep.mrv reaction.mrv reaction_adv.mrv resonance.mrv skeleton.mrv skeleton_adv.mrv splitarray.mrv
T.tutorial 3 lewis.structures marvinsketch.introduction multistep.mechanism
Chapter X: Extra Questions: Multistep Synthesis
X.1 7 001 002 003 004 005 006 007
Chapter 1: The Structures of Organic Molecules
1.1 9 001 002 003 004 005 006 007 008 009
1.2 4 001 002 003 004
1.3 1 001
1.4 3 001 002 003
1.5 10 001 002 003 004 005 006 007 008 009 010
Chapter 2: Bonding in Organic Molecules
2.1 5 001 002 003 004 005
2.3 1 001
2.5 1 001
2.6 1 001
2.8 9 001 002 003 004 005 006 007 008 009
Chapter 3: The Conformations of Organic Molecules
3.1 7 001 002 003 004 005 006 007
3.3 10 001 002 003 004 005 006 007 008 009 010
3.4 1 001
Chapter 4: The Stereochemistry of Organic Molecules
4.1 5 001 002 003 004 005
4.2 7 001 002 003 004 005 006 007
4.3 6 001 002 003 004 005 006
4.4 6 001 002 003 004 005 006
Chapter 5: Chemical Reactions and Mechanisms
5.2 15 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015
5.3 12 001 002 003 004 005 006 006.alt 007 008 009 010 010.alt
5.4 6 001 002 003 004 005 006
Chapter 6: Substitution Reactions of Alkyl Halides
6.2 15 001 002 002.alt 003 003.alt 004 004.alt 005 006 007 007.alt 008 009 010 011
6.3 9 001 002 003 004 005 006 007 008 009
6.4 2 001 002
Chapter 7: Substitution Reactions of Alcohols and Related Compounds
7.1 2 001 002
7.2 9 001 002 003 004 005 006 007 007.alt 008
Chapter 8: Elimination Reactions of Alkyl Halides, Alcohols, and Related Compounds
8.1 2 001 002
8.2 15 001 002 003 004 005 006 007 008 008.alt 009 010 011 012 012.alt 013
8.3 8 001 002 003 004 005 006 007 008
Chapter 9: Addition Reactions of Alkenes and Alkynes
9.1 14 001 002 003 004 004.alt 005 006 007 008 009 010 010.alt 011 012
9.2 2 001 002
9.4 2 001 002
9.5 4 001 002 003 004
Chapter 10: Addition Reactions of Conjugated Dienes
10.2 1 001
10.3 1 001
10.4 15 001 002 003 004 005 006 006.alt 007 008 009 010 011 012 013 013.alt
Chapter 11: Oxidation and Reduction Reactions
11.1 1 001
11.2 10 001 002 003 004 005 006 007 008 009 009.alt
11.3 7 001 002 003 004 005 006 007
Chapter 12: Free Radical Reactions
12.1 17 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017
12.2 5 001 002 003 004 005
12.3 4 001 002 003 004
Chapter 13: Proton and Carbon NMR Spectroscopy
13.1 1 001
13.2 1 001
13.3 7 001 002 003 004 005 006 007
13.6 1 001
Chapter 14: Determining the Structures of Organic Molecules
14.1 4 001 002 003 004
14.2 6 001 002 003 004 005 006
14.3 6 001 002 003 004 005 006
14.4 2 001 002
Chapter 15: Organometallic Reagents and Chemical Synthesis
15.2 22 001 002 003 004 004.alt 005 006 007 008 009 010 011 011.alt 012 012.alt 013 014 015 016 017 018 019
15.3 9 001 002 003 004 005 006 007 008 009
15.4 2 001 002
15.5 2 001 002
Chapter 16: Asymmetric Reactions and Synthesis
16.2 1 001
16.3 1 001
Chapter 17: The Chemistry of Benzene and Its Derivatives
17.1 15 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015
17.2 10 001 001.alt 002 003 003.alt 004 005 006 007 008
17.3 9 001 002 003 004 005 006 007 008 009
17.4 21 001 002 003 004 004.alt 005 006 007 008 009 010 011 012 013 014 015 016 017 018 019 020
Chapter 18: Nucleophilic Addition Reactions of Aldehydes and Ketones
18.2 5 001 002 003 004 005
18.3 5 001 002 003 004 004.alt
18.4 6 001 002 003 004 005 006
Chapter 19: Addition–Substitution Reactions of Aldehydes and Ketones: Carbohydrate Chemistry
19.1 4 001 002 003 004
19.2 3 001 001.alt 002
19.3 9 001 002 003 004 005 006 007 008 009
Chapter 20: Addition–Elimination Reactions of Aldehydes and Ketones
20.2 3 001 002 003
20.3 2 001 002
20.4 4 001 002 002.alt 003
Chapter 21: Addition–Elimination Reactions of Carboxylic Acids and Derivatives
21.2 3 001 002 003
21.3 3 001 002 003
21.4 9 001 002 003 004 005 006 007 008 009
21.5 5 001 002 003 004 005
21.6 4 001 002 003 004
21.7 2 001 002
21.8 3 001 002 003
Chapter 22: The Acid–Base Chemistry of Carbonyl Compounds
22.2 4 001 002 003 004
22.3 3 001 002 003
22.4 5 001 002 003 004 005
22.5 1 001
Chapter 23: The Nucleophilic Addition Reactions of Enolate Ions
23.1 2 001 002
23.2 8 001 002 003 004 005 006 007 008
23.3 4 001 002 003 004
23.4 2 001 002
Chapter 24: Conjugate Addition Reactions of Unsaturated Carbonyl Compounds
24.2 1 001
24.3 2 001 002
Chapter 25: The Chemistry of Polycyclic and Heterocyclic Arenes
25.4 1 001
Chapter 26: Polymers and Polymerization
26.2 1 001
26.3 6 001 002 002.alt 003 004 004.alt
26.4 1 001
Chapter 27: Amino Acids, Peptides, and Proteins
27.1 3 001 002 003
27.2 1 001
27.4 7 001 002 003 004 004.alt 005 006
27.5 1 001
Chapter 28: Nucleic Acids and Molecular Recognition
28.1 3 001 002 003
28.2 2 001 002
Total 534