Preface
To the Instructor
Acknowledgments
Introduction
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
Purification
Measurement of Physical Constants
Physical Examination
Ignition Test
Classification
Solubility Tests
Classification Tests
Spectral Analysis
Infrared Spectra
NMR Spectra
Identification
List of Possibilities
Additional Tests and Data
Preparation of Derivatives
Report
Exercises
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
Bibliography
Index
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