Organic Chemistry Practice Problems at Michigan State University

The following problems are meant to be useful study tools for students involved in most undergraduate organic chemistry courses.  The problems have been color-coded to indicate whether they are:

1.  Generally useful,
2.  Most likely to be useful to students in year long, rather than survey courses,
3.  Most likely to be useful only to students in courses for chemistry majors and/or honors students.

Some of these problems make use of a Molecular Editor drawing application.  To practice using this editor Click Here.

General Questions
  1. Question: Common Valencies
  2. Question: Shapes of Simple Molecules
  3. Question: Empirical & Molecular Formulas
  4. Question: Line & Condensed Structural Formulas
  5. Question: Identifying Line Formulas
  6. Question: Carbon Atom Classification
  7. Question: Structural Formulas & Alkane Nomenclature
  8. Question: Drawing Formulas from Models
  9. Question: Polar Covalent Bonds
  10. Question: Lewis Formulas & Formal Charges
  11. Question: Formal Charges
  12. Question: Interpreting Molecular Formulas of Hydrocarbons
  13. Question: Analyzing Molecular Formulas
  14. Question: Formal Charges & Resonance
  15. Question: Resonance Stabilization
  16. Question: Hybridization & Bonding
  17. Question: Identifying Hybridization States I
  18. Question: Identifying Hybridization States II
  19. Question: Identifying Functional Groups
  20. Question: Functional Groups I
  21. Question: Functional Groups II
  22. Question: Structurally Equivalent Groups-1
  23. Question: Structurally Equivalent Groups-2
  24. Question: Hydrogen Bonding
  25. Question: Boiling Points
  26. Question: Solubility in Water
  27. Question: Enol Tautomers
  28. Question: Heat of Reaction
Nomenclature
  1. Question: Identfying IUPAC suffixes
  2. Question: Alkanes & cycloalkanes
  3. Question: IUPAC Nomenclature Practice Problems
  4. Question: Matching ring compounds to their names
  5. Question: Alkanes: Drawing formulas from names.
  6. Question: Cyclolkanes: Drawing formulas from names.
  7. Question: Alkenes & Cycloalkenes: Drawing formulas from names.
  8. Question: Drawing alkene formulas from names.
  9. Question: Drawing alkyne formulas from names.
  10. Question: Substituted benzenes. Drawing formulas from names.
  11. Question: Matching alcohols to their names I
  12. Question: Alcohols: drawing formulas from names.
  13. Question: Drawing alcohol formulas from names.
  14. Question: Matching amines to their names
  15. Question: Amines: Drawing formulas from names.
  16. Question: Drawing amine formulas from names.
  17. Question: Aldehydes & Ketones: drawing formulas from names..
  18. Question: Drawing aldehyde & ketone formulas from names.
  19. Question: Drawing carboxylic acid & derivative formulas.
  20. Question: Drawing carboxylic derivatives formulas from names.
  21. Question: Assorted Nomenclature Problems.
Conformations and Stereochemistry
  1. Question: Identifying Stereoisomers of Substituted Cycloalkanes
  2. Question: A Structure Recognition Problem
  3. Question: Identifying Conformations for Specific Compounds
  4. Question: Identifying Gauche Interactions
  5. Question: Identifying Axial & Equatorial Substituents
  6. Question: Identifying Symmetry Elements & Dissymmetry
  7. Question: Alkene Isomers
  8. Question: E / Z Notation & The Sequence Rule
  9. Question: Identifying Chiral Structures
  10. Question: Identifying Chirality & Symmetry Elements
  11. Question: A Stereochemical Terminology Problem
  12. Question: Classification of Stereoisomers
  13. Question: Drawing Stereoisomers of Inositol
  14. Question: Locating & Naming Stereogenic Centers
  15. Question: CIP Configurational Notation
  16. Question: Assigning CIP Notation 1
  17. Question: Assigning CIP Notation 2
  18. Question: Assigning CIP Notation 3
  19. Question: Relationship of Isomer Pairs
  20. Question: Evaluating Structural Formulas I
  21. Question: Evaluating Structural Formulas II
  22. Question: Drawing Stereoisomers from Names
  23. Question: Drawing Stereoisomeric Products
  24. Question: Recognizing Stereoisomers I
  25. Question: Recognizing Stereoisomers II
  26. Question: Recognizing Stereoisomers III
Spectroscopy
  1. Question: Structurally Equivalent Groups-1
  2. Question: Structurally Equivalent Groups-2
  3. Question: Basic NMR Spectroscopy
  4. Question: Basic NMR Spectroscopy II
  5. Question: Spin-Spin Splitting
  6. Question: Selecting a Spectroscopic Tool I
  7. Question: Selecting a Spectroscopic Tool II
  8. Question: Interpreting a 1H nmr spectrum I
  9. Question: Interpreting a 1H nmr spectrum II
  10. Question: Determining a Molecular Formula
  11. Question: Mass Spectroscopy I
  12. Question: Mass Spectroscopy II
  13. Question: Mass Spectroscopy III
  14. Question: Mass Spectroscopy IV
  15. Question: Mass Spectroscopy V
  16. Question: Mass Spectroscopy VI
  17. Question: Mass Spectroscopy VII
  18. Question: Structural Formulas from Spectroscopic Data
  19. Question: Infrared Spectra Assignments
  20. Question: Using MS & IR Spectra
  21. Question: An Assortment of Spectroscopy Problems
  22. Question: Additional Spectroscopy Problems
  23. Question: Identifying Conjugation in Dienes
  24. Question: A Structural Puzzle based on Spectroscopic & Chemical Data
Aromaticity
  1. Question: Aromaticity and the Huckel Rule I
  2. Question: Aromaticity and the Huckel Rule II
Acidity and Basicity
  1. Question: Identifying Acid & Base Components
  2. Question: Acid-Base Equilibrium Relationships
  3. Question: Relative Acid Strength I
  4. Question: Relative Acid Strength II
  5. Question: Relative Acid Strength III
  6. Question: Relative Base Strengths
  7. Question: Drawing Conjugate Acid Structures
  8. Question: Drawing Conjugate Base Structures
  9. Question: Estimating pKa's I
  10. Question: Estimating pKa's II
Mechanisms
  1. Question: Mechanism of Acid-Catalyzed Acetal Formation
  2. Question: Mechanism of Acid-Catalyzed Enamine Formation
  3. Question: Evaluating Curved Arrows 1
  4. Question: Evaluating Curved Arrows 2
  5. Question: Placing Curved Arrows
  General Reactivity and Reactions

    Oxidation and Reduction

  1. Question: Oxidation/Reduction
  2. Electrophiles and Nucleophiles

  3. Question: Identifying Electrophiles
  4. Question: Identifying Nucleophiles
  5. Functional Group Reactions

  6. Question: Reactions of an Alkane
  7. Question: Halogenation of Alkanes
  8. Question: Reactions with Bromine
  9. Question: Halogenation of Alkanes
  10. Question: Alkene Transformations 1
  11. Question: Alkene Transformations 2
  12. Question: Alkene Transformations 3
  13. Question: Alkene Transformations 4
  14. Question: Alkene Reactions 5
  15. Question: Random Alkene Reactions
  16. Question: Drawing Addition Reactions
  17. Question: Stereospecificity in Addition Reactions
  18. Question: Alkyne Reactions
  19. Question: Alkyne Transformations
  20. Question: Electrophilic Addition Reactions to Conjugated Dienes
  21. Question: Relative Reactivity of Halide Substitutions
  22. Question: Halide Substitutions and Eliminations
  23. Question: Reactions of Organic Halides I
  24. Question: Reactions of Organic Halides II
  25. Question: Random Alkyl Halide Reactions
  26. Question: Functional Relationships of Alcohols
  27. Question: Reactions of Alcohols & Phenols
  28. Question: Random Alcohol Reactions
  29. Question: Ether Cleavage Reactions
  30. Question: Reactions of Epoxides
  31. Question: Electrophilic Aromatic Substitution
  32. Question: Directing Effects in Electrophilic Aromatic Substitution
  33. Question: Products in Electrophilic Aromatic Substitution
  34. Question: Reactions of Propene
  35. Question: Drawing Structures for Ozonolysis Products
  36. Question: Drawing Reactant Structures from Ozonolysis Products
  37. Question: Reactions of Isobutanol
  38. Question: Reactions of Aldehydes
  39. Question: Addition Reactions of Aldehydes & Ketones
  40. Question: Reactions of Aldehydes & Ketones I
  41. Question: Reactions of Aldehydes & Ketones II
  42. Question: Reactions of Carboxylic Acids I
  43. Question: Reactions of Carboxylic Acids II
  44. Question: Carbonyl Compounds
  45. Question: Drawing Structures for Hydrolysis Products
  46. Question: Preparation of Amines
  47. Question: Reactions of Amines I
  48. Question: Reactions of Amines II
  49. Question: Hofmann Elimination of Amines
  50. Question: General Reactivity & Reaction Products
  51. Question: Structural Puzzle 1
  52. Question: Structural Puzzle 2
  53. Question: Structural Puzzle 3
  54. Question: Structural Puzzle 4
  55. Other Reactivity Questions

  56. Question: Classifying Reactions & Acid / Base Catalysis
  57. Question: Nucleophilic Reaction Mechanisms
  58. Question: A Matching Problem for Aldehydes & Ketones
  59. Question: A Selection Problem for Aldehyde & Ketone Chemistry
  60. Question: Suitability of Diels Alder Reactants
  61. Question: Reactivity of Dienes with Maleic Anhydride
  62. Question: Products from Diels-Alder Cycloaddition Reactions
  63. Question: Reactants Leading to Diels-Alder Cycloaddition Adducts
  64. Question: A Comprehensive Diels-Alder Question
  65. Question: Aldol Condensation Reactants
  66. Question: Claisen Condensation Reactants
  67. Question: Solvent Selection
Molecular Rearrangement
  1. Question: Drawing Formulas of Rearrangement Products
  2. Question: Rearrangement in Synthesis
  3. Question: Drawing Rearrangement Mechanisms
  4. Question: A More Challenging Mechanism Problem
Synthesis
  1. Question: Reactions that Generate Aldehydes & Ketones
  2. Question: A Reagent Selection Problem
  3. Question: Introduction to Multistep Synthesis
  4. Question: Use of Nitrobenzene in Synthesis
  5. Question: Condensation Reactions in Synthesis
  6. Question: Predicting Products from Multistep Syntheses I
  7. Question: Predicting Products from Multistep Syntheses II
  8. Question: Devising Steps in a Multistep Synthesis I
  9. Question: Devising Steps in a Multistep Synthesis II
  10. Question: A Multistep Synthesis I
  11. Question: A Multistep Synthesis II
  12. Question: A Multistep Synthesis III
  13. Question: A Multistep Synthesis Exercise
Polymers
  1. Question: Identifying Monomers
  2. Question: Chemical Resistance of Plastics
  3. Question: Preparation of Poly(vinyl alcohol)
  4. Question: Stereoisomerism of Polymers
  5. Question: Polymerization of β-Propiolactone
Biomolecules
  1. Question: Identifying Natural Product Classes
  2. Question: Aldohexose Configurations
  3. Question: Stereoisomer Notation in Monosaccharides
  4. Question: The Wohl Degradation of Monosaccharides
  5. Question: Pyranose & Furanose Forms of Monosaccharides
  6. Question: Disaccharide Structures
  7. Question: Triglycerides
  8. Question: Triglyceride Chirality
  9. Question: The Isoprene Rule
  10. Question: Structure of Terpenes
  11. Question: Properties of Amino Acids
  12. Question: Primary Structure of a Peptide
Problems by Abby Parrill
  1. Question: Acid-Base Properties of Amino Acids I
  2. Question: Acid-Base Properties of Amino Acids II
  3. Question: Acid-Base Properties of Amino Acids III
  4. Question: Protein Sequencing I
  5. Question: Protein Sequencing II
  6. Question: Protein Sequencing III
  7. Question: Protein Sequencing IV
  8. Question: Protein Folding I
  9. Question: Protein Folding II
  10. Question: Protein Secondary Structure
  11. Question: Protein Tertiary Structure
  12. Question: Protein Synthesis I
  13. Question: Protein Synthesis II
  14. Question: Protein Synthesis III
  15. Question: DNA Pairing I
  16. Question: DNA Pairing II
  17. Question: DNA Helical Forms
  18. Question: DNA Synthesis

Full discussions of the topics covered by these problems are available in the Virtual Textbook of Organic Chemistry.
The following button will activate a random display of problems concerning the reactivity of common functional groups.
A large collection of multiple choice problems, similar to those used in standardized examinations, may be reached by clicking here

Most of these Interactive Organic Chemistry Practice Problems have been developed by Professor William Reusch.
1999 William Reusch, All rights reserved. Comments, questions and errors should be sent to whreusch@msu.edu.
The Virtual Text and some of the problems make use of either the CHIME plugin, or Jmol. Click on the name for information and a free copy.
If possible, monitor resolutions of 1024 x 768 or 1152 x 870 should be used.

Concerning Computer Problems

The practice problems offered here are chiefly interactive, and should provide a useful assessment of understanding at various stages in the development of the subject.
Since problem solving is essential to achieving an effective mastery of the subject, it is recommended that many more problems be worked. Most organic chemistry textbooks contain a broad assortment of suitable problems, and paperback collections of practice problems are also available.

The following web-sites provide nice collections of problems and answers:

MIT Open CourseWare
Reaction quizzes and summaries from Towson University
Electronic flashcards from Ohio State University
Concept questions from University of Wisconsin
Practice problems from UCLA
Arrow Pushing Tutorial
BestChoice, University of Auckland Demo may be used
Spectroscopy problems from Notre Dame

Department of Chemistry
Michigan State University
East Lansing, MI  48824

For a useful collection of study materials, including links to other sites, visit the Organic chemistry tool-kit.
Prepared by Bob Hanson, St. Olaf College