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: Line & Condensed Structural Formulas
  3. Question: Identifying Line Formulas
  4. Question: Shapes of Simple Molecules
  5. Question: Structural Formulas & Alkane Nomenclature
  6. Question: Polar Covalent Bonds
  7. Question: Lewis Formulas & Formal Charges
  8. Question: Formal Charges
  9. Question: Interpreting Molecular Formulas of Hydrocarbons
  10. Question: Analyzing Molecular Formulas
  11. Question: Formal Charges & Resonance
  12. Question: Resonance Stabilization
  13. Question: Hybridization & Bonding I
  14. Question: Functional Groups I
  15. Question: Functional Groups II
  16. Question: Hydrogen Bonding
  17. Question: Boiling Points
  18. Question: Solubility in Water
  19. Question: Enol Tautomers
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: Alkene nomenclature: names & formulas.
  9. Question: Drawing alkene formulas from names.
  10. Question: Drawing alkyne formulas from names.
  11. Question: Substituted benzenes. Drawing formulas from names.
  12. Question: Matching alcohols to their names I
  13. Question: Alcohols: drawing formulas from names.
  14. Question: Drawing alcohol formulas from names.
  15. Question: Matching amines to their names
  16. Question: Amines: Drawing formulas from names.
  17. Question: Drawing amine formulas from names.
  18. Question: Aldehydes & Ketones: drawing formulas from names..
  19. Question: Drawing aldehyde & ketone formulas from names.
  20. Question: Drawing carboxylic acid & derivative formulas.
  21. Question: Drawing carboxylic derivatives formulas from names.
  22. Question: Assorted Nomenclature Problems.
Conformations and Stereochemistry
  1. Question: A Structure Recognition Problem
  2. Question: Identifying Conformations for Specific Compounds
  3. Question: Identifying Gauche Interactions
  4. Question: Identifying Axial & Equatorial Substituents
  5. Question: Identifying Symmetry Elements & Dissymmetry
  6. Question: Alkene Isomers
  7. Question: E / Z Notation & The Sequence Rule
  8. Question: Identifying Chiral Structures
  9. Question: Identifying Chirality & Symmetry Elements
  10. Question: A Stereochemical Terminology Problem
  11. Question: Classification of Stereoisomers
  12. Question: Locating & Naming Stereogenic Centers
  13. Question: CIP Configurational Notation
  14. Question: Assigning CIP Notation 1
  15. Question: Assigning CIP Notation 2
  16. Question: Relationship of Isomer Pairs
  17. Question: Drawing Stereoisomers from Names
  18. Question: Drawing Stereoisomeric Products
Spectroscopy
  1. Question: Structurally Equivalent Groups-1
  2. Question: Structurally Equivalent Groups-2
  3. Question: Basic NMR Spectroscopy
  4. Question: Spin-Spin Splitting
  5. Question: Selecting a Spectroscopic Tool I
  6. Question: Selecting a Spectroscopic Tool II
  7. Question: Interpreting a 1H nmr spectrum
  8. Question: Determining a Molecular Formula
  9. Question: Mass Spectroscopy I
  10. Question: Mass Spectroscopy II
  11. Question: Mass Spectroscopy III
  12. Question: Mass Spectroscopy IV
  13. Question: Mass Spectroscopy V
  14. Question: Mass Spectroscopy VI
  15. Question: Mass Spectroscopy VII
  16. Question: Structural Formulas from Spectroscopic Data
  17. Question: Infrared Spectra Assignments
  18. Question: Using MS & IR Spectra
  19. Question: An Assortment of Spectroscopy Problems
  20. Question: Additional Spectroscopy Problems
  21. 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
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
   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: Reactions with Bromine
  6. Question: Halogenation of Alkanes
  7. Question: Alkene Transformations 1
  8. Question: Alkene Transformations 2
  9. Question: Alkene Reactions 3
  10. Question: Random Alkene Reactions
  11. Question: Stereospecificity in Addition Reactions
  12. Question: Alkyne Reactions
  13. Question: Alkyne Transformations
  14. Question: Electrophilic Addition Reactions to Conjugated Dienes
  15. Question: Relative Reactivity of Halide Substitutions
  16. Question: Halide Substitutions and Eliminations
  17. Question: Reactions of Organic Halides I
  18. Question: Reactions of Organic Halides II
  19. Question: Random Alkyl Halide Reactions
  20. Question: Functional Relationships of Alcohols
  21. Question: Reactions of Alcohols & Phenols
  22. Question: Random Alcohol Reactions
  23. Question: Ether Cleavage Reactions
  24. Question: Reactions of Epoxides
  25. Question: Electrophilic Aromatic Substitution
  26. Question: Directing Effects in Electrophilic Aromatic Substitution
  27. Question: Products in Electrophilic Aromatic Substitution
  28. Question: Reactions of Propene
  29. Question: Drawing Structures for Ozonolysis Products
  30. Question: Drawing Reactant Structures from Ozonolysis Products
  31. Question: Reactions of Isobutanol
  32. Question: Reactions of Aldehydes
  33. Question: Addition Reactions of Aldehydes & Ketones
  34. Question: Reactions of Aldehydes & Ketones I
  35. Question: Reactions of Aldehydes & Ketones II
  36. Question: Reactions of Carboxylic Acids I
  37. Question: Reactions of Carboxylic Acids II
  38. Question: Carbonyl Compounds
  39. Question: Drawing Structures for Hydrolysis Products
  40. Question: Preparation of Amines
  41. Question: Reactions of Amines I
  42. Question: Reactions of Amines II
  43. Question: Hofmann Elimination of Amines
  44. Question: General Reactivity & Reaction Products
  45. Question: Structural Puzzle 1
  46. Question: Structural Puzzle 2
  47. Question: Structural Puzzle 3
  48. Question: Structural Puzzle 4

    49. Other Reactivity Questions

  49. Question: Classifying Reactions & Acid / Base Catalysis
  50. Question: Nucleophilic Reaction Mechanisms
  51. Question: A Matching Problem for Aldehydes & Ketones
  52. Question: A Selection Problem for Aldehyde & Ketone Chemistry
  53. Question: Suitability of Diels Alder Reactants
  54. Question: Reactivity of Dienes with Maleic Anhydride
  55. Question: Products from Diels-Alder Cycloaddition Reactions
  56. Question: Reactants Leading to Diels-Alder Cycloaddition Adducts
  57. Question: A Comprehensive Diels-Alder Question
  58. Question: Aldol Condensation Reactants
  59. Question: Claisen Condensation Reactants
  60. 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: Stereoisomer Notation in Monosaccharides
  3. Question: The Wohl Degradation of Monosaccharides
  4. Question: Pyranose & Furanose Forms of Monosaccharides
  5. Question: Disaccharide Structures
  6. Question: Triglycerides
  7. Question: Triglyceride Chirality
  8. Question: The Isoprene Rule
  9. Question: Structure of Terpenes
  10. Question: Properties of Amino Acids
  11. 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.

Most of the Interactive Organic Chemistry Practice Problems have been developed by Professor William Reusch.
©1999 William Reusch, All rights reserved.
The Virtual Text and some of the problems make use of the CHIME plugin. Click on the name to obtain a free copy.
If possible, monitor resolutions of 1024 x 768 or 1152 x 870 should be used.

NEW  

  A large collection of multiple choice problems, similar to those used in standardized examinations, may be reached by clicking here.

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:

Reaction quizzes and summaries from Towson University
Electronic flashcards from Ohio State University
Concept questions from University of Wisconsin
Practice problems from UCLA
Spectroscopy problems from Notre Dame

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

 Attention Graduate and Advanced Undergraduate Students

A wonderful source of challenging problems, assembled by Prof. David Evans and associates at Harvard University, may be examined by clicking Here.

  

Department of Chemistry
Michigan State University
East Lansing, MI  48824