Reaction green metrics: problems, exercises, and solutions

605 Pages·2019·66.878 MB·English

by  Andraos, John

Reaction Green Metrics
Problems, Exercises, and Solutions

Reaction Green Metrics
Problems, Exercises, and Solutions
By
John Andraos
CareerChem
Toronto, ON
Canada
[email protected]
CRC Press
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Contents Contents
Dedication
Dr. Christopher Randall Schmid
(1959– 2007)
Inaugural Editor of Organic Process Research & Development

Contents
Preface.......................................................................................................................xi
Chapter 1 Introduction ..........................................................................................1
1.1 What This Book Is About ..........................................................2
1.2 Structure ....................................................................................3
1.3 How to Use the Book .................................................................3
Chapter 2 Constitution of a Chemical Reaction and Reaction Balancing ............5
2.1 Identifying Components of any Chemical Reaction .................5
2.1.1 Terms, Definitions, and Examples ...............................5
2.1.2 Problems .......................................................................9
2.2 Balancing Chemical Equations ...............................................10
2.2.1 Terms, Definitions, and Examples .............................10
2.2.2 Problems .....................................................................30
2.3 Redox Reactions ......................................................................31
2.3.1 Terms, Definitions, and Examples .............................32
2.3.2 Determining Oxidation States of Atoms in
Structures ...................................................................35
2.3.3 Balancing Redox Reactions ........................................41
2.3.4 Oxidation Number Analysis .......................................58
2.3.5 Problems .....................................................................66
References ..........................................................................................79
Chapter 3 Experimental Description of Chemical Reactions .............................83
3.1 Structure of Literature Experimental Procedures ...................83
3.2 Quality of Literature Experimental Procedures ......................84
3.3 Problems ..................................................................................95
References ..........................................................................................97
Chapter 4 Chemical Reaction Classifications .....................................................99
4.1 Identifying Types of Reactions ................................................99
4.1.1 Terms, Definitions, and Examples .............................99
4.1.2 Problems ...................................................................136
4.2 Nomenclature for Ring Construction Strategies ...................138
4.2.1 Terms, Definitions, and Examples ...........................138
4.2.2 Problems ...................................................................177
References ........................................................................................195
vii
viii Contents
Chapter 5 Drawing Chemical Structures ..........................................................197
5.1 Principle of Conservation of Structural Aspect ....................198
5.1.1 Examples ..................................................................200
5.1.2 Problems ...................................................................204
5.2 Writing a Reaction Mechanism .............................................207
5.2.1 Elementary Steps ......................................................207
5.2.2 Curly Arrow Notation ..............................................207
5.2.3 Catalytic Cycles ........................................................213
5.2.4 Electrochemical Reactions .......................................224
5.3 Target Bond Mapping ............................................................235
5.3.1 Problems ...................................................................263
5.4 Tracking Oxidation State Changes ........................................267
5.4.1 Problems ...................................................................285
References ........................................................................................289
Chapter 6 Waste Production and Input Material Consumption ........................293
6.1 Definition of What Constitutes Waste ...................................297
6.1.1 Terms, Definitions, and Examples ...........................297
6.2 Metrics Associated with Waste Production ...........................299
6.2.1 Terms, Definitions, and Examples ...........................299
6.3 Metrics Associated with Input Consumption ........................306
6.3.1 Terms, Definitions, and Examples ...........................306
6.4 Metrics Associated with Product Formation .........................313
6.4.1 Terms, Definitions, and Examples ...........................313
6.5 Connections and Hierarchy ...................................................319
6.6 Worked Examples ..................................................................335
6.7 Problems ................................................................................414
References ........................................................................................443
Chapter 7 Intrinsic Greenness ...........................................................................447
7.1 Minimum Atom Economy.....................................................447
7.1.1 Terms, Definitions, and Examples ...........................447
7.1.2 Problems ...................................................................455
7.2 Probability of Determining Intrinsic Greenness for any
Chemical Reaction ................................................................469
7.2.1 Terms, Definitions, and Examples ...........................469
7.2.2 Problems ...................................................................495
7.3 Automated Determination of AE(min), p Intrinsic
Greenness, and Hypsicity for any Chemical Reaction ..........498
7.3.1 Calcu lator -Prob abili ty-In trins ic-Gr eenne ss.xl s
Spreadsheet ...............................................................498
7.3.2 Trends for Named Organic Reactions ......................499
References ........................................................................................513
Contents ix
Chapter 8 Automated Computation for a Single Reaction ................................515
8.1 Excel Spreadsheet Tools: Part 1 ............................................515
8.1.1 Densities.xls .............................................................515
8.1.2 Densities-of-Acid-Solutions.xls ................................515
8.1.3 Densities-of-Base-Solutions.xls ................................516
8.1.4 Densities-of-Carbohydrate-Solutions.xls .................517
8.1.5 Flash-Chromatography-Mass-Intensity-Template.xls ....518
8.1.6 Template-Reaction.xls ..............................................521
8.1.7 Template-Reaction-Input-Costs.xls ..........................521
8.2 Evaluating Material Efficiency for a Single
Chemical Reaction ................................................................521
8.3 Evaluating Input Cost for a Single
Chemical Reaction ................................................................524
8.4 Problems ................................................................................528
References ........................................................................................577
Appendix: Other Terminologies .........................................................................581
Index ......................................................................................................................589