Contents
Graphical Abstracts for the Experiments
13
Strategies and Tools
Chapter 1:
Introduction
1.1
19
The Many Benefits of Organic Chemistry - The Impact of Organic Chemistry
on Our Lives
Chapter 2:
Chapter 3:
------
1.2
The Need for Sustainable Chemistry
21
1.3
Green Chemistry: New Approaches to Important Problems
22
Summary
24
Identification and Evaluation of Chemical Hazards
25
2.1
Chemical Hazards
26
2.2
Quantitative Evaluation of Chemical Hazards
27
2.3
Classes of Hazardous Substances
28
Summary
34
Chemical Exposure and Environmental Contamination
3.1 Health Risks and Environmental Impact Require Exposure
35
3.2 Volatile Organic Compounds (VOCs)
36
3.3 Emissions from Human Activities
Chapter 4:
19
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35
---
--
36
3.4 Natural Sources of Environmental Exposure to Hazardous Substances
41
Summary
42
Sources of Information about Chemical Hazards
43
4.1
Evaluation of Hazards
43
Sources of Information about Chemical Hazards
45
4.2
-
Summary
Chapter 5:
-
48
Introduction to Green Chemistry
5.1
5.2
-
----- _..49
Traditional Approaches to the Reduction of Environmental Contamination and
Human Health Risk
49
Strategies of Green Chemistry
50
10
5.3 Tools of Green Chemistry
Summary
Chapter 6:
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Typical Solvents and Problems Associated with Their Use
6.2
Traditional Approaches to Solvent Handling and Disposal
6.3
Green Approaches to Solvents
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7.2
Safer Reagents
78
7.3
Nontraditional reagents
7.4
The "Three R' s" of Green Chemistry
00
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79
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79
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86
88
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Reaction Design and Efficiency
Reaction Efficiency
79
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Alternative Reagents
64
m
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Reagents
7.1
8. 1
55
m
0
Summary
Chapter 8:
------ --.55
6.1
Alternative
53
m
u
Alternati ve Sol vents
Summary
Chapter 7:
m
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89
-_m-- -
-- ---
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89
--
8.2 Experimental Atom Economy
91
8.3 Alternative Reaction Design
8.4
Alternati ve Synthetic Pathways
Summary
Chapter 9:
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9. 1
AI ternative
Feedstocks
9.2
Alternative Products
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99
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The Big Picture and Green Chemistry Metrics ---m
l02
10.1 The Challenge and Complexity of Implementing Green Chemistry
Summary
_.93
95
96
o
Alternative Feedstocks and Products
Summary
Chapter 10:
-- --
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106
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Laboratory Experiments
Chapter 11:
Preface to the Experimental Section
11.1 Introductory Comments
11.2 General Laboratory
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Safety Issues
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11
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108
08
l 09
11.3 Working With Chemicals
110
11.4 Waste Disposal/Recyc1ing
111
11.5 Sources of Chemical Safety Infonnation
111
11.6 Laboratory Notebooks and Reports
111
Experiment 1:
Solventless Reactions: The Aldol Reaction
115
Experiment 2:
Bromination of An Alkene: Preparation of Stilbene Dibromide
120
Experiment 3:
A Greener Bromination of Stilbene
125
Experiment 4:
Preparation and Distillation of Cyc1ohexene
129
Experiment 5:
Synthesis and Recrystallization of Adipic Acid
135
Experiment 6:
Oxidative Coupling of Alkynes: The Glaser-Eglinton-Hay
Experiment 7:
Gas-Phase Synthesis, Column Chromatography and Visible Spectroscopy of
00
Coupling
142
5,10,15,20- Tetrapheny lporphyrin
152
Experiment 8:
Microwave Synthesis of 5,10,15,20- Tetrapheny lporphyrin
159
Experiment 9:
Metallation of 5,10,15,20- Tetraphenylporphyrin
163
Experiment 10: Measuring Solvent Effects: Kinetics of Hydrolysis of tert-Butyl Chloride
167
Experiment 11: Molecular Mechanics Modeling
174
Experiment 12: Electrophilic Aromatic Iodination
182
Experiment 13: Palladium-Catalyzed
Alkyne Coupling/Intramolecular
Alkyne Addition: Natural
Product Synthesis
189
Experiment 14: Resin-Based Oxidation Chemistry
197
Experiment 15: Carbonyl Chemistry: Thiamine-Mediated Benzoin Condensation of Furfural
201
Experiment 16: Solid-Phase Photochemistry
206
Experiment 17: Applications of Organic Chemistry: Patterning Surfaces With Molecular Films
211
Experiment 18: The Friedel-Crafts Reaction: Acetylation of Ferrocene
225
Experiment 19: Combinatorial Chemistry: Antibiotic Drug Discovery
231
Appendix A:
239
The Twelve Principles of Green Chemistry
Index
241
12