Organic Chemistry 5th edition

Textbook Cover

William H. Brown, Christopher S. Foote, Brent L. Iverson and Eric Anslyn
Publisher: Cengage Learning


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  • 0: Tutorials & Templates (15)
  • 1: Covalent Bonding and Shapes of Molecules (20)
  • 2: Alkanes and Cycloalkanes (28)
  • 3: Stereochemistry and Chirality (23)
  • 4: Acids and Bases (21)
  • 5: Alkenes (12)
  • 6: Reactions of Alkenes (16)
  • 7: Alkynes (13)
  • 8: Haloalkanes, halogenation, and Radical Reactions (12)
  • 9: Nucleophilic Substitution and β Elimination (56)
  • 10: Alcohols (25)
  • 11: Ethers, Sulfides, and Epoxides (12)
  • 12: Infrared Spectroscopy (6)
  • 13: Nuclear Magnetic Resonance Spectroscopy (12)
  • 14: Mass Spectrometry (7)
  • 15: Introduction to Organometallic Compounds (20)
  • 16: Aldehydes and Ketones (17)
  • 17: Carboxylic Acids (13)
  • 18: Functional Derivatives of Carboxylic Acids (20)
  • 19: Enolate Anions and Enamines (24)
  • 20: Conjugated Systems (13)
  • 21: Benzene and the Concept of Aromaticity (14)
  • 22: Reactions of Benzene and its Derivatives (35)
  • 23: Amines (35)
  • 24: Carbon-Carbon Bond Formation and Synthesis (22)
  • 25: Carbohydrates (12)
  • 26: Lipids (14)
  • 27: Amino Acids and Proteins (13)
  • 28: Nucleic Acids (6)
  • 29: Organic Polymer Chemistry (8)

The WebAssign questions for this textbook are from a collection of questions developed by Dr. Kay Sandberg, an award winning organic chemistry instructor at North Carolina State University. These questions, covering the main topics in organic chemistry, have been correlated as closely as possible to the appropriate chapters in this textbook. This independent question collection provides a more secure solution to online homework for organic chemistry, since most organic chemistry textbook questions have detailed solutions published in the accompanying student solution guide. However, because these questions were not originally written for this textbook, it is recommended that you check each assigned problem to see if the material required for completing the question has been covered in your class. The question set has been extensively class-tested in large enrollment courses at NC State.

Question Collection Features: Questions requiring automatic assessment of student-drawn structures, including skeletal structures, Lewis structures, reaction mechanisms with electron-flow arrows ("pushing electrons"), isotopically-labeled reactions, and multi-step syntheses, use the popular MarvinSketch application. WebAssign grades these structures automatically, checking for stereo features, rings, chains, etc.

Questions requiring automatic assessment of chemical formulas and reaction equations use WebAssign's chemPad, an intuitive answer-entry palette with over 150 lines of intelligent answer feedback.

Other questions use a variety of response types, including fill-in-the-blank, multiple-choice, multiple-select and numerical entry.

Notice to Adopters of Previous Editions: Previous editions used the JME Molecular Editor to draw and automatically grade structures. This new edition upgrades that limited functionality by replacing it with the more powerful MarvinSketch application. For this new edition, we have also upgraded and increased the number of randomizations per question. Even questions using images and multiple-choice answers have been randomized where possible.



Question Group Key
tutorial - Tutorials
template - Templates
P - Problems


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


Group Quantity Questions
Chapter 0: Tutorials & Templates
0.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
0.tutorial 3 lewis.structures marvinsketch.introduction multistep.mechanism
Chapter 1: Covalent Bonding and Shapes of Molecules
1.P 20 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017 018 019 020
Chapter 2: Alkanes and Cycloalkanes
2.P 28 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017 018 019 020 021 022 023 024 025 026 027 028
Chapter 3: Stereochemistry and Chirality
3.P 23 001 002 003 004 005 006 007 008 009 010 010.alt 011 012 013 014 015 016 017 018 019 020 021 022
Chapter 4: Acids and Bases
4.P 21 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017 018 019 020 021
Chapter 5: Alkenes
5.P 12 001 002 003 004 005 006 007 008 009 010 011 012
Chapter 6: Reactions of Alkenes
6.P 16 001 002 002.alt 003 004 005 006 007 008 009 010 011 012 013 014 015
Chapter 7: Alkynes
7.P 13 001 002 003 004 005 006 007 008 009 010 011 012 013
Chapter 8: Haloalkanes, halogenation, and Radical Reactions
8.P 12 001 002 003 004 005 006 007 008 009 010 011 012
Chapter 9: Nucleophilic Substitution and β Elimination
9.P 56 001 002 002.alt 003 003.alt 004 004.alt 005 006 007 008 009 009.alt 010 011 012 012.alt 013 014 015 016 017 018 019 020 020.alt 021 022 023 024 025 026 027 028 029 029.alt 030 031 032 033 034 035 036 037 038 039 040 041 042 043 044 045 046 047 048 049
Chapter 10: Alcohols
10.P 25 001 002 003 004 005 006 007 008 009 010 011 012 013 014 014.alt 015 016 017 018 019 020 021 022 023 024
Chapter 11: Ethers, Sulfides, and Epoxides
11.P 12 001 002 003 004.alt 005 006 007 008 009 010 011 012
Chapter 12: Infrared Spectroscopy
12.P 6 001 002 003 004 005 006
Chapter 13: Nuclear Magnetic Resonance Spectroscopy
13.P 12 001 002 003 004 005 006 007 008 009 010 011 012
Chapter 14: Mass Spectrometry
14.P 7 001 002 003 004 005 006 007
Chapter 15: Introduction to Organometallic Compounds
15.P 20 001 002 003 004 004.alt 005 006 007 008 009 010 011 012 013 014 014.alt 015 016 017 018
Chapter 16: Aldehydes and Ketones
16.P 17 001 002 003 004 005 006 006.alt 007 008 009 010 011 012 013 014 015 016
Chapter 17: Carboxylic Acids
17.P 13 001 002 003 004 005 005.alt 006 007 008 009 010 011 012
Chapter 18: Functional Derivatives of Carboxylic Acids
18.P 20 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017 018 019 020
Chapter 19: Enolate Anions and Enamines
19.P 24 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017 018 019 020 021 022 023 024
Chapter 20: Conjugated Systems
20.P 13 001 002 003 004 005 006 007 008 009 010 011 012 012.alt
Chapter 21: Benzene and the Concept of Aromaticity
21.P 14 001 002 003 004 005 006 007 008 009 010 011 012 013 014
Chapter 22: Reactions of Benzene and its Derivatives
22.P 35 001 002 003 003.alt 004 005 006 007 008 009 010 010.alt 011 012 012.alt 013 014 015 016 017 018 019 020 021 022 023 024 025 026 027 028 029 030 031 032
Chapter 23: Amines
23.P 35 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017 018 019 020 021 022 023 024 024.alt 025 026 027 028 029 030 031 032 033 034
Chapter 24: Carbon-Carbon Bond Formation and Synthesis
24.P 22 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017 018 019 020 021 021.alt
Chapter 25: Carbohydrates
25.P 12 001 002 003 004 005 006 007 008 009 010 011 012
Chapter 26: Lipids
26.P 14 001 002 003 003.alt 004 005 005.alt 006 007 008 009 010 011 012
Chapter 27: Amino Acids and Proteins
27.P 13 001 002 003 004 005 006 007 007.alt 008 009 010 011 012
Chapter 28: Nucleic Acids
28.P 6 001 002 003 004 005 006
Chapter 29: Organic Polymer Chemistry
29.P 8 001 002 003 003.alt 004 005 005.alt 006
Total 544