Organic Chemistry: Structure and Function 5th edition

Textbook Cover

K. Peter C. Vollhardt and Neil E. Schore
Publisher: Macmillan Learning


Access is contingent on use of this textbook in the instructor's classroom.

  • 1: Structure and Bonding in Organic Molecules (16)
  • 2: Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules (16)
  • 3: Reactions of Alkanes: Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity (8)
  • 4: Cycloalkanes (12)
  • 5: Stereoisomers (14)
  • 6: Properties and Reactions of Haloalkanes: Biomolecular Nucleophilic Substitution (4)
  • 7: Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination (10)
  • 8: Hydroxy Functional GroupL Alcohols: Properties, Preparation, and Strategy of Synthesis (10)
  • 9: Further Reactions of Alcohols and the Chemistry of Ethers (28)
  • 10: Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure (10)
  • 11: Alkenes; Infrared Spectroscopy and Mass Spectrometry (12)
  • 12: Reactions of Alkenes (28)
  • 13: Alkynes: the Carbon-Carbon Triple Bond (14)
  • 14: Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy (14)
  • 15: Benzene and Aromaticity: Electrophilic Aromatic Substitution (10)
  • 16: Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity (29)
  • 17: Aldehydes and Ketones: The Carbonyl Group (31)
  • 18: Enols, Enolates, and the Aldol Condensation: α, β-Unsaturated Aldehydes and Ketones (22)
  • 19: Carboxylic Acids (16)
  • 20: Carboxylic Acid Derivatives (22)
  • 21: Amines and Their Derivatives: Functional Groups Containing Nitrogen (16)
  • 22: Chemistry of Benzene Substituents: Alkylbenzenes, Phenols, and Benzenamines (18)
  • 23: Ester Enolates and the Claisen Condensation: Synthesis of β-Dicarbonyl Compounds; Acyl Anion Equivalents (12)
  • 24: Carbohydrates: Polyfunctional Compounds in Nature (14)
  • 25: Heterocycles: Heteroatoms in Cyclic Organic Compounds (3)
  • 26: Amino Acids, Peptides, Proteins, and Nucleic Acids: Nitrogen-Containing Polymers in Nature (10)
  • MCAT: MCAT (16)
  • 28: Quantum Mechanics and Atomic Physics
  • 29: The Nucleus
  • 30: Nuclear Reactions and Elementary Particles
The WebAssign questions for this textbook are from a set of questions developed by Dr. Kay Sandberg, an experienced 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 chapter in the textbook. 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.

Because it is customary in organic chemistry to publish a complete student solution guide for every end-of-chapter question, the student guide renders the textbook end-of-chapter questions unusable for an online homework system. Dr. Sandberg's set of questions provides an excellent solution to this problem.

A variety of response types are used in multipart questions such as fill-in-the blank, multiple choice, multiselect and numerical. Most importantly, there are many questions that require the students to draw a skeletal structure for an organic molecule using a web-based, online drawing tool in WebAssign. WebAssign grades these structures automatically, checking for stereo features, rings, chains, etc. by creating a unique SMILES string.

The question set has been extensively class-tested in multiple 200-student courses at NC State.

As often as possible, variables, numbers, or words have been randomized so that each student will receive a unique version.

You are free to duplicate a question and change it as you like for your class.
Question Group Key
kas - Kay Sandberg Questions
MCAT - Medical College Admissions Test
E - Review Exercises


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


Group Quantity Questions
Chapter 1: Structure and Bonding in Organic Molecules
1.kas 16 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16
Chapter 2: Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules
2.kas 16 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16
Chapter 3: Reactions of Alkanes: Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity
3.E 4 01 02 03 04
3.kas 4 01 02 03 04
Chapter 4: Cycloalkanes
4.kas 12 01 02 03 04 05 06 07 08 09 10 11 12
Chapter 5: Stereoisomers
5.kas 14 02 03 04 05 06 07 08 09 10 11 12 13 14 15
Chapter 6: Properties and Reactions of Haloalkanes: Biomolecular Nucleophilic Substitution
6.E 2 01 02
6.kas 2 01 03
Chapter 7: Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination
7.kas 10 01 02 04 05 06 07 08 09 10 11
Chapter 8: Hydroxy Functional GroupL Alcohols: Properties, Preparation, and Strategy of Synthesis
8.kas 10 01 02 03 05 06 07 08 09 10 11
Chapter 9: Further Reactions of Alcohols and the Chemistry of Ethers
9.kas 28 01 02 03 04 06 07 08 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29
Chapter 10: Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure
10.kas 10 01 02 03 04 05 06 07 08 09 10
Chapter 11: Alkenes; Infrared Spectroscopy and Mass Spectrometry
11.kas 12 01 02 03 04 05 06 07 08 09 10 11 12
Chapter 12: Reactions of Alkenes
12.kas 28 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28
Chapter 13: Alkynes: the Carbon-Carbon Triple Bond
13.kas 14 01 02 03 04 05 06 07 08 09 10 11 12 13 14
Chapter 14: Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy
14.kas 14 01 02 03 04 05 06 07 08 09 10 11 12 13 14
Chapter 15: Benzene and Aromaticity: Electrophilic Aromatic Substitution
15.E 5 01 02 03 04 05
15.kas 5 01 02 03 04 05
Chapter 16: Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity
16.kas 29 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29
Chapter 17: Aldehydes and Ketones: The Carbonyl Group
17.kas 31 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31
Chapter 18: Enols, Enolates, and the Aldol Condensation: α, β-Unsaturated Aldehydes and Ketones
18.kas 22 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16 17 18 19 20 21 22
Chapter 19: Carboxylic Acids
19.kas 16 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16
Chapter 20: Carboxylic Acid Derivatives
20.kas 22 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16 17 18 19 20 21 22
Chapter 21: Amines and Their Derivatives: Functional Groups Containing Nitrogen
21.E 8 01 02 03 04 05 06 07 08
21.kas 8 01 02 03 04 05 06 07 08
Chapter 22: Chemistry of Benzene Substituents: Alkylbenzenes, Phenols, and Benzenamines
22.kas 18 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16 17 18
Chapter 23: Ester Enolates and the Claisen Condensation: Synthesis of β-Dicarbonyl Compounds; Acyl Anion Equivalents
23.kas 12 01 02 03 04 05 06 07 08 09 10 11 12
Chapter 24: Carbohydrates: Polyfunctional Compounds in Nature
24.E 7 01 02 03 04 05 06 07
24.kas 7 01 02 03 04 05 06 07
Chapter 25: Heterocycles: Heteroatoms in Cyclic Organic Compounds
25.E 2 01 02
25.kas 1 01
Chapter 26: Amino Acids, Peptides, Proteins, and Nucleic Acids: Nitrogen-Containing Polymers in Nature
26.kas 10 01 02 03 04 05 06 07 08 09 10
Chapter MCAT: MCAT
MCAT 16 01 02 03 04 05 06 07 08 09 10 11 12 13 14 15 16
Total 415