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

  2. Question: Identifying Electrophiles
  3. Question: Identifying Nucleophiles

    4. Functional Group Reactions

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

    53. Other Reactivity Questions

  53. Question: Classifying Reactions & Acid / Base Catalysis
  54. Question: Nucleophilic Reaction Mechanisms
  55. Question: A Matching Problem for Aldehydes & Ketones
  56. Question: A Selection Problem for Aldehyde & Ketone Chemistry
  57. Question: Suitability of Diels Alder Reactants
  58. Question: Reactivity of Dienes with Maleic Anhydride
  59. Question: Products from Diels-Alder Cycloaddition Reactions
  60. Question: Reactants Leading to Diels-Alder Cycloaddition Adducts
  61. Question: A Comprehensive Diels-Alder Question
  62. Question: Aldol Condensation Reactants
  63. Question: Claisen Condensation Reactants
  64. 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