Table of contents for Multiscale operational organic chemistry : a problem-solving approach to the laboratory course / John W. Lehman.

Bibliographic record and links to related information available from the Library of Congress catalog.

Note: Contents data are machine generated based on pre-publication provided by the publisher. Contents may have variations from the printed book or be incomplete or contain other coding.


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Contents
Preface 
To the Instructor 
Acknowledgments
Introduction 
Problem Solving in the Organic Chemistry Lab 
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	Learning Basic Operations. The Effect of pH on a Food Preservative 
2	Extraction and Evaporation. Separating the Components of "Panacetin" 
3	Recrystallization and Melting-Point Measurement. Identifying a Constituent of "Panacetin" 
4	Heating Under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil 
5	Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil 
6	Fractional Distillation. Separation of Petroleum Hydrocarbons 
7	Addition, Sublimation. A Green Synthesis of Camphor 
8	Boiling Point, Refractive Index. Identification of a Petroleum Hydrocarbon 
9	Column Chromatography, UV-VIS Spectrometry. Isolation and Isomerization of Lycopene from Tomato Paste 
10	Steam Distillation, Infrared Spectrometry. Isolation and Identification of the Major Constituent of Clove Oil 
11	Thin-Layer Chromatography, NMR Spectrometry. Identification of Unknown Ketones 
12	Vacuum Distillation, Optical Rotation. 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 Solvolysis 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 Trityl Carbocation 
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 Reeaction 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-meta-toluamide 
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 Reaction of Bromotriphenylmethane 
18	Preparation and Properties of a Gaseous Alkene 
19	Addition of Iodine to 
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 
The 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 
a	Heat Sources 
b	Smooth Boiling Devices 
c	Heating Under Reflux 
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 
a	Liquid-Liquid Extraction 
b	Salting Out 
c	Liquid-Solid Extraction 
19	Evaporation 611
20	Steam Distillation 617
21	Column Chromatography 621
a	Liquid-Solid Column Chromatography 
b	Flash Chromatography 
c	Reversed-Phase 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 
a Washing Solids
b Drying Solids 
27	Cleaning and Drying Gases 
E	Purification Operations 
28	Recrystallization 
a	Recrystallization from a Single Solvent 
b	Recrystallization from Mixed Solvents 
c	Choosing a Recrystallization Solvent 
29	Sublimation 
30	Simple Distillation 
a	Distillation of Liquids 
b	Distillation of Solids 
31	Vacuum Distillation 
32	Fractional Distillation 
F	Measuring Physical Constants 
33	Melting Point 
34	Boiling Point 
a	Distillation Boiling Point 
b	Capillary-Tube 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 
a Spectrometry 
b	 Spectrometry 
41	Ultraviolet-Visible Spectrometry 
a	UV-VIS Spectra 
b	Colorimetry 
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 

Library of Congress Subject Headings for this publication:

Chemistry, Organic -- Laboratory manuals.