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What the Experts Say About this Book (continued from the book’s back cover) “Keeping the logic of organic chemistry, Professor Green leads the reader through the most important topics of this field of science in an unusual fashion. Reading the manuscript allows the knowledge to be absorbed without an awareness that one is learning. The book is therefore not only very useful, but even very entertaining. Important parts of the history of chemistry are embedded in an excellent manner into the appropriate places of the text allowing the subject to be presented in a broad sensible context. I recommend this book to all students and teachers dealing with organic chemistry.” — Peter Huszthy, Budapest University of Technology and Economics, Hungary “This unusual textbook boldly questions our current approach to teaching organic chemistry and provides an alternative that is both unique and sensible. All too often, textbooks of organic chemistry present context-less elementary principles that rely on rote memorization, and only later do the “cool” and breathtaking applications of those principles come to be discussed. By drawing on riveting examples, this book reverses that approach by discovering the elementary principles in the wonderful applications of organic chemistry in our lives and uses this context to spur student learning. Such an approach, which more closely aligns with the natural learning process, could well be the answer to teaching this fascinating subject in a fun and effective way.” — Dasan M. Thamattoor, Colby College “I looked at this book out of pure curiosity. I opened the book at random and started to read. After a while I became so interested that I read on and on and missed a prior appointment. The book describes organic chemistry, the way it came about in the last 200 years. It is an irresistible read.” — Arnost Reiser, Polytechnic Institute of New York University “The idea of your book is new and revolutionary. It may take time for many people to accept it, but I consider your book highly valuable. I would encourage you to publish it and believe that eventually many people would like it.” — Lin Pu, University of Virginia, Charlottesville “This is an organic chemistry textbook that deviates from the traditional bottom- up approach, which begins with atoms and ends with biomolecules. In stark contrast, this book takes us first to the real molecular world through an active dialog that illustrates the importance of organic chemistry to our lives — what organic chemistry deals with. Perhaps, many students will then grasp the basic concepts for the first time. The book should be a useful reference and a gem for years to come” — Pedro Cintas, Facultad de Ciencias-UEX, Badajoz, Spain “You have confronted, in the specific case of organic chemistry, the two big problems in the teaching of experimental sciences in the University at the twenty first century. 1) How is it possible to learn the permanently increasing amount of knowledge necessary to achieve expertise in a discipline of science, which is additionally including information from other scientific fields? 2) How is it possible for this learning to occur by real understanding, which is the only path to true expertise, and not by simply overcoming evaluations and examinations? Organic Chemistry Principles in Context, in starting from a complex relevant topic, which is the final objective of learning, dissects the elements and basic scientific knowledge necessary to explain the topic. Taking a story telling historical approach attracts the student’s attention, which together with starting with an attractive topic is very probably the only way to explain complementary scientific disciplines in superior education.” — Ribo, JM, Department of Organic Chemistry and Institute of Cosmos Science, University of Barcelona, Catalonia, Spain “This book is anything but traditional. It opens with carbohydrate chemistry, a subject often relegated to the end of a beginning organic course because it is ‘so complicated’. Mark Green makes in a few beginning pages this “complicated” subject simplicity itself and moves effortlessly on into stereochemistry, organic reaction mechanisms and pretty much everything else that belongs in an organic chemistry course. The difference is that he tells organic chemistry as an adventure story. Everything is there. It’s fun. It’s interesting. It’s about chemistry and people and how it all came about and what it means. Surely this is why students (should) go to the university — to learn about ideas rather than only facts. The good student will learn organic chemistry the way it should be learned from this book. Curriculum committees are likely to find this book a square peg in a round hole. Maybe we need a bit more of that for good teaching?” — Richard M. Kellogg, University of Groningen (retired), Syncom Corporation, The Netherlands. “Starting with the pictures of the scientists that significantly contributed to our knowledge as a human factor, organic chemistry is brought to us as an adventure, an exciting story. Almost all important issues dealt with in organic chemistry appear in this book, however, not in the conventional order. With complex, real life examples, all fundamentals of organic chemistry are explained. The way the references to the scientists are made makes the book a report of a human endeavor coherent in time and place and not simply a collection of facts. The book is an entertaining, context-based treatise of organic chemistry that is very rich for students and teachers with at least the basic knowledge presented in general chemistry. The book is decorated with more than 250 figures and includes more than 640 problems. The textbook is written by a well- documented and extremely knowledgeable organic chemist.” — J. A. J. M. Vekemans, Eindhoven University of Technology, The Netherlands “This book should be read by every organic chemist, academic or industrial.” Harold Wittcoff, Process Evaluation and Research Planning, Nexant, Inc. (ret.) “For beginning students, it is not necessary to study all the details and all the reactions, old and new, in organic chemistry. The important thing is to study the fundamental principles, which brings the student to understand how the science is the product of human works and thoughts, the art and culture of organic chemistry. Your textbook just fits to this objective, I believe. The book starts with: “Both cellulose and starch are polymers”. At first students might ask why the book starts with this sentence. As they are reading Chapter 1, they see that an organic molecule is an artistic composition in three dimensions and come to understand the beauty of this three dimensional character, which is well represented by the difference between cellulose and starch. Finally their study will lead them to understand and even create new molecules using the art and culture of organic chemistry. This book is not an accumulation or a compilation of organic reactions but shows an interesting series of historical stories or victories and how organic chemistry has progressed. Nylons, elastomers and polyolefins are important stories of macromolecular chemistry from both a scientific and industrial point of view, with attention to scientists who played important roles. Your narrative description and writing style makes it easy for the students to understand the principle and importance in our life of the area which they are studying. The developments of these macromolecules are good examples of the fusion of science and engineering. I can turn over every page excitingly imagining what is written on the next page. The book is helpful and useful for every student to find the ways of the futures which they should follow.” — Koichi Hatada, Professor Emeritus of Osaka University “Any serious students or practitioners of Organic Chemistry will realize significant benefits and deepen their understanding of this beautiful science by reading this book.” — James A. Moore, Rensselaer Polytechnic Institute “The book’s one-of-a-kind approach to teaching organic chemistry gets rid of the fears that usually come with a college organic chemistry textbook. The historical accounts, along with important organic chemistry principles, are narrated in such a unique way that makes the whole subject fun to learn! Prof. Green’s book prepares students interested in pursuing science by teaching the fundamental ideas in chemistry and the end-of-the-chapter questions guide students through thinking like an organic chemist. This is so unlike all of the other textbooks that teach the subject only through pages and pages of reactions to be memorized! ” — Jinhui Zhao, Biomolecular Science B.S., Class of 2012, Polytechnic Institute of NYU “Organic Chemistry Principles in Context is a wonderful textbook for any student of organic chemistry. This textbook harmoniously combines fundamental chemistry principles with the historical context of their development, allowing the student to understand not only the chemical mechanisms, but also the social and scientific context of the development of organic chemistry. But most importantly, this textbook manages to avoid all of the clutter seen in conventional organic chemistry textbooks — given by the huge lists of chemical reactions that students have to memorize, along with their catalytic conditions — and focuses the students’ attention on the basic mechanisms that underlie this wonderful scientific field. Personally, I think that by doing this, Professor Mark Green has managed to remove the fear of memorizing organic chemistry from the hearts of the students and replace that fear with a desire to understand organic chemistry. I have used this textbook during my two semesters of Organic Chemistry with Professor Green and it has helped me understand organic chemistry at a level which allowed me to pursue a Masters degree in Chemistry and also obtain a high score on the MCAT exam.” — Radu Iliescu, Biomolecular Science B.S./Chemistry M.S., Class of 2013, Polytechnic Institute of NYU ORGANIC CHEMISTRY Principles in Context Copyright © 2012 by Mark M. Green, second printing 2013 All rights reserved No part of this book may be reproduced or transmitted in any form or by any electronic, digital or mechanical means, including photocopying, recording or by any information storage and retrieval system, without the express written permission of the publisher, except where permitted by law. ISBN 978-0-615-70271-1 Published By: ScienceFromAway Publishing New York, NY 10014 [email protected] Book Designer, Robert L. Lascaro www.lascarodesign.com Typeset in Minion Pro Display type: Helvetica Neue Printer: CreateSpace, a divison of Amazon.com Inc. Library of Congress Cataloging-in-Publication Data “Those ignorant of the historical development of science are not likely ever to understand fully the nature of science and scientific research.” Sir Hans Adolf Krebs, 1970. WITH GRATITUDE AND LOVE TO MY PARENTS, who opened the door to accomplishment for their children by making so much more out of life than they were given, and to Ruth Schulman for demonstrating the value of strength in adversity and her love and support, and always to my many students over the years who showed me the treasures accessible to a teacher’s life. To my wife, children, sons-in-law and grandchildren—thank you for family life and all its wonders, which continue to supply the foundation. Finally, to my teachers for showing me the way, Kurt Mislow, Carl Djerassi, Herbert Morawetz, Arnost Reiser and Harold Wittcoff.