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Reaction green metrics: problems, exercises, and solutions PDF

605 Pages·2019·66.878 MB·English
by  AndraosJohn
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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 Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2019 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed on acid-free paper International Standard Book Number-13: 978-1-138-38895-6 (Hardback) International Standard Book Number-13: 978-1-138-38894-9 (Paperback) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged, please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, no part of this book may be reprinted, reproduced, transmit- ted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, with- out written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com 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

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