Operational Organic Chemistry

Prentice Hall
John W. Lehman  
Total pages
February 2017
Related Titles


This comprehensive laboratory text provides a thorough introduction to all of the significant operations used in the organic lab and includes a large selection of traditional-scale experiments and minilabs. Its unique problem-solving approach encourages students to think in the laboratory by solving a scientific problem in the process of carrying out each experiment.


The Fourth Edition contains a new introductory section, “Chemistry and the Environment,” which includes a discussion of the principles of green chemistry. Several green experiments have been added, and some experiments from the previous editions have been revised to make them greener.


A logical organization of lab operations - Helps students understand the purposes of different operations and the relationship between them. Makes it easy to access and use the operations.


A guide to success in the lab - Informs students what to expect in their organic chemistry lab course, helps allay their fears about dangerous chemicals, and tells them how to get organized and how to work 

   effectively with others.


A comprehensive section on lab safety - Reduces the likelihood of lab accidents. Informs the student of what to do in case of an accident.


A scientific methodology section - Teaches students how to apply sound scientific methodology in solving problems so they learn how scientists work.


Up-to-date information about modern instrumental techniques - Keeps students abreast of the current techniques and instruments of the field.


Useful appendixes:

    - Contain useful information about how to keep a lab notebook, write lab reports, perform stoichiometric calculations, prepare experiment plans, identify unknown compounds, identify lab equipment, and search the chemical literature.


    - Gives information that students will need to plan, perform, and write up experiments. Relieves the instructor of having to provide such information in write-ups or lectures.

New to this Edition

New introductory section, “Chemistry and the Environment,” which includes a discussion of the principles of green chemistry, with descriptions of how these principles can be applied in the lab.


• Sections on personal protective equipment and on finding and using chemical safety information have been added under the “Laboratory Safety” heading.


Six new experiments have been added (Experiments 22, 24, 31, 35, 40, and 41), replacing six experiments that were in the third edition.


• Several green experiments have been added, and some experiments from the previous editions have been revised to make them greener.


New troubleshooting sections (“When Things Go Wrong”) in most operations - Helps students recover from mistakes or at least understand what went wrong when they have performed an operation incorrectly.


New section on Chemistry and the Environment -Helps instructors and students carry out lab experiments in a more environmentally responsible manner.


• Addition of a brief summary at the beginning of each set of operations - Helps students understand the purposes of the operations and how they relate to one another.


New section on finding and using chemical safety information - Teaches students more about the safety information available (such as MSDS's) and how to access it.


• Addition of a new operation “Excluding Air from Reaction Mixtures” - Enables students to carry out experiments involving oxygen-sensitive chemicals.


• Addition of new information about infrared sampling techniques - Helps students use new sampling techniques involving ATRs and disposable IR cards and helps them use other techniques more effectively.


• Addition of calculations for solution preparation - Allows students to prepare solutions from stock chemicals when necessary.


• Updated bibliographic sections - Includes references copyrighted as recently as 2008.


• The Bibliography has been updated to include more current literature sources, necessitating a revision of Appendix VII, “The Chemical Literature.”


Table of Contents


To the Instructor




Problem Solving in the Organic Chemistry Laboratory

Scientific Methodology

Organization of This Book

A Guide to Success in the Organic Chemistry Lab


Laboratory Safety

Safety Standards

Protecting Yourself

Preventing Laboratory Accidents

Reacting to Accidents: First Aid

Reacting to Accidents: Fire

Chemical Hazards

Finding and Using Chemical Safety Information


Chemistry and the Environment

Disposal of Hazardous Wastes

Green Chemistry


Part I Mastering the Operations

1. The Effect of pH on a Food Preservative

2. Separating the Components of “Panacetin”

3. Identifying a Constituent of “Panacetin”

4. Synthesis of Salicylic Acid from Wintergreen Oil

5. Preparation of Synthetic Banana Oil

6. Separation of Petroleum Hydrocarbons

7. A Green Synthesis of Camphor

8. Identification of a Petroleum Hydrocarbon

9. Isolation and Isomerization of Lycopene from Tomato Paste

10. Isolation and Identification of the Major Constituent of Clove Oil

11. Identification of Unknown Ketones

12. The Optical Activity of -Pinene: A Chemical Mystery


Part II Correlated Laboratory Experiments

13. Investigation of a Chemical Bond by Infrared Spectrometry

14. Properties of Common Functional Groups

15. Thin-Layer Chromatographic Analysis of Drug Components

16. Separation of an Alkane Clathrate

17. Isomers and Isomerization Reactions

18. Structures and Properties of Stereoisomers

19. Bridgehead Reactivity in an SN1Solvolysis Reaction

20. Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile

21. Dehydration of Methylcyclohexanols and the Evelyn Effect

22. Testing Markovnikov's Rule

23. Stereochemistry of Bromine Addition to trans-Cinnamic Acid

24. A Green Synthesis of Adipic Acid

25. Preparation of Bromotriphenylmethane and the Trityl Free Radical

26. Chain-Growth Polymerization of Styrene and Methyl Methacrylate

27. Synthesis of Ethanol by Fermentation

28. Reaction of Butanols with Hydrobromic Acid

29. Borohydride Reduction of Vanillin to Vanillyl Alcohol

30. Synthesis of Triphenylmethanol and the TritylCarbocation

31. An Unexpected Reaction of 2,3-Dimethyl-2,3-butanediol

32. Identification of a Conjugated Diene from Eucalyptus Oil

33. Spectral Identification of Monoterpenes

34. Synthesis and Spectral Analysis of Aspirin

35. Directive Effects in the Bromination of Vanillin

36. Mechanism of the Nitration of Arenes by Nitronium Fluoborate

37. Friedel-Crafts Acylation of Anisole

38. Determination of the Structure of a Natural Product in Anise Oil

39. Identification of an Oxygen-Containing Organic Compound

40. Oxidation of the Insect Repellent “6-12”

41. Isomerization of a Cyclic Ketone

42. A Wittig Reaction of trans-Cinnamaldehyde

43. Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone

44. Electronic Effect of a para-Iodo Substituent

45. Synthesis and Identification of an Unknown Carboxylic Acid

46. Preparation of the Insect Repellent N,N-Diethyl-metatoluamide

47. Synthesis of Dimedone and Measurement of Its Tautomeric Equilibrium Constant

48. Preparation of Para Red and Related Azo Dyes

49. Reaction of Phthalimide with Sodium Hypochlorite

50. Identification of an Unknown Amine

51. Preparation and Mass Spectrum of 2-Phenylindole

52. Nucleophilic Strength and Reactivity in SNAr Reactions

53. Structure of an Unknown D-Hexose

54. Fatty Acid Content of Commercial Cooking Oils

55. Structure of an Unknown Dipeptide

56. Multistep Synthesis of Benzilic Acid from Benzaldehyde

57. Using the Chemical Literature in an Organic Synthesis

58. A Research Project in Organic Chemistry


Part III Minilabs

1. Making Useful Laboratory Items

2. Extraction of Iodine by Dichloromethane

3. Purification of an Unknown Compound by Recrystallization

4. Developing and Testing a Hypothesis

5. Preparation of Acetate Esters

6. Gas Chromatographic Analysis of Commercial Xylene

7. Isolation of an Expectorant from Cough Capsules

8. A Missing-Label Puzzle

9. Paper Chromatography of Dyes in Commercial Drink Mixes

10. Gas Chromatographic Analysis of an Essential Oil from Orange Peel

11. Identification of an Unknown Felt-Tip Pen Ink by TLC

12. Optical Rotation of Turpentine

13. The Structures of Organic Molecules

14. Who Else Has My Compound?

15. Isomers and Molecular Structure

16. Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions

17. An SN1 Reaction of Bromotriphenylmethane

18. Preparation and Properties of a Gaseous Alkene

19. Addition of Iodine to a-Pinene

20. Unsaturation in Commercial Products

21. Free-Radical Stability

22. The Nylon Rope Trick

23. Nucleophilic Substitution Rates of Alcohols

24. Photoreduction of Benzophenone

25. Oxidation of Alcohols by Potassium Permanganate

26. Preparation of a Fluorescent Dye

27. Diels-Alder Reaction of Maleic Anhydride and Furan

28. Identification of an Unknown Arene by NMR Spectrometry

29. Interpretation of a Mass Spectrum

30. Nitration of Naphthalene

31. Preparation of Carbocations by the Friedel-Crafts Reaction

32. Air Oxidation of Fluorene to 9-Fluorenone

33. A Nucleophilic Addition-Elimination Reaction of Benzil

34. Preparation of Aldol Condensation Products

35. A Spontaneous Reaction of Benzaldehyde

36. Acid-Base Strengths of Organic Compounds

37. Hydrolysis Rates of Esters

38. Preparation of Benzamide

39. Synthesis of Dimedone Derivatives of Benzaldehyde

40. A Diazonium Salt Reaction of 2-Aminobenzoic Acid

41. Beckmann Rearrangement of Benzophenone Oxime

42. Dyeing with Indigo

43. Reactions of Monosaccharides with Phenols

44. Isolation of Trimyristin from Nutmeg

45. Preparation of a Soap Using a Phase-Transfer Catalyst

46. Isolation of a Protein from Milk


Part IV Qualitative Organic Analysis

An Overview of Qual Organic


Preliminary Work


Measurement of Physical Constants

Physical Examination

Ignition Test



Solubility Tests

Classification Tests


Spectral Analysis

Infrared Spectra

NMR Spectra



List of Possibilities

Additional Tests and Data

Preparation of Derivatives





Part V Laboratory Operations

A) Basic Operations

1. Cleaning and Drying Glassware

2. Using Specialized Glassware

3. Using Glass Rod and Tubing

4. Weighing

5. Measuring Volume

6. Making Transfers


B) Operations for Conducting Chemical Reactions

7. Heating

8. Cooling

9. Temperature Monitoring

10. Mixing

11. Addition of Reactants

12. Excluding Water from Reaction Mixtures

13. Excluding Air from Reaction Mixtures

14. Trapping Gases


C) Separation Operations

15. Gravity Filtration

16. Vacuum Filtration

17. Centrifugation

18. Extraction

19. Evaporation

20. Steam Distillation

21. Column Chromatography

22. Thin-Layer Chromatography

23. Paper Chromatography


D) Washing and Drying Operations

24. Washing Liquids

25. Drying Liquids

26. Washing and Drying Solids

27. Cleaning and Drying Gases


E) Purification Operations

28. Recrystallization

29. Sublimation

30. Simple Distillation

31. Vacuum Distillation

32. Fractional Distillation


F) Measuring Physical Constants

33. Melting Point

34. Boiling Point

35. Refractive Index

36. Optical Rotation


G. Instrumental Analysis

37. Gas Chromatography

38. High-Performance Liquid Chromatography

39. Infrared Spectrometry

40. Nuclear Magnetic Resonance Spectrometry

41. Ultraviolet-Visible Spectrometry

42. Mass Spectrometry


Appendixes and Bibliography

I Laboratory Equipment

II Keeping a Laboratory Notebook

III Writing a Laboratory Report

IV Calculations for Organic Synthesis

V Planning an Experiment

VI Properties of Organic Compounds

VII The Chemical Literature





John W. Lehman received his Ph.D. in chemistry from the University of Colorado in Boulder. He has taught chemistry for 35 years at Lake Superior State University, a small university in Michigan's scenic Upper Peninsula. In recognition of his teaching skills, he received the State of Michigan's Teaching Excellence Award in 1990. In 2001 he funded a chemistry scholarship to help bring outstanding students into the chemistry program at Lake Superior State University. His groundbreaking lab text, Operational Organic Chemistry, was first published in 1981, and he has written three additional books for the organic chemistry laboratory. 

Instructor Resources