Student Reasoning in Organic Chemistry Research Advances and Evidence-based Instructional Practices Advances in Chemistry Education Series Editor-in-chief: Keith S. Taber, University of Cambridge, UK Series editors: Avi Hofstein, Weizmann Institute of Science, Israel Vicente Talanquer, University of Arizona, USA David Treagust, Curtin University, Australia Editorial Advisory Board: Mei-Hung Chiu, National Taiwan Normal University, Taiwan, Rosaria da Silva Justi, Universidade Federal de Minas Gerais, Brazil, Onno De Jong, Utrecht University, Netherlands, Ingo Eilks, University of Bremen, Germany, Murat Kahveci, Çanakkale Onsekiz Mart University, Turkey, Vanessa Kind, Durham University, UK, Stacey Lowery Bretz, Miami University, USA, Hannah Sevian, University of Massachusetts Boston, USA, Daniel Tan, Nanyang Technolog- ical University, Singapore, Marcy Towns, Purdue University, USA, Georgios Tsaparlis, University of Ioannina, Greece. Titles in the Series: 1: Professional Development of Chemistry Teachers: Theory and Practice 2: Argumentation in Chemistry Education: Research, Policy and Practice 3: The Nature of the Chemical Concept: Re-constructing Chemical Knowl- edge in Teaching and Learning 4: Creative Chemists: Strategies for Teaching and Learning 5: Engaging Learners with Chemistry: Projects to Stimulate Interest and Participation 6: The Johnstone Triangle: The Key to Understanding Chemistry 7: Problems and Problem Solving in Chemistry Education 8: Teaching and Learning in the School Chemistry Laboratory 9: Nanochemistry for Chemistry Educators 10: Student Reasoning in Organic Chemistry: Research Advances and Evi- dence-based Instructional Practices How to obtain future titles on publication: A standing order plan is available for this series. A standing order will bring delivery of each new volume immediately on publication. For further information please contact: Book Sales Department, Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge, CB4 0WF, UK Telephone: +44 (0)1223 420066, Fax: +44 (0)1223 420247 Email: [email protected] Visit our website at www.rsc.org/books Student Reasoning in Organic Chemistry By Nicole Graulich Justus-Liebig-University Gießen, Germany Email: [email protected] and Ginger Shultz University of Michigan, USA Email: [email protected] Advances in Chemistry Education Series No. 10 Print ISBN: 978-1-83916-491-0 PDF ISBN: 978-1-83916-778-2 EPUB ISBN: 978-1-83916-779-9 Print ISSN: 2056-9335 Electronic ISSN: 2056-9343 A catalogue record for this book is available from the British Library © Royal Society of Chemistry 2023 All rights reserved Apart from fair dealing for the purposes of research for non-commercial purposes or for private study, criticism or review, as permitted under the Copyright, Designs and Patents Act 1988 and the Copyright and Related Rights Regulations 2003, this publication may not be reproduced, stored or transmitted, in any form or by any means, without the prior permission in writing of The Royal Society of Chemistry or the copyright owner, or in the case of reproduction in accordance with the terms of licences issued by the Copyright Licensing Agency in the UK, or in accordance with the terms of the licences issued by the appropriate Reproduction Rights Organization outside the UK. Enquiries concerning reproduction outside the terms stated here should be sent to The Royal Society of Chemistry at the address printed on this page. Whilst this material has been produced with all due care, The Royal Society of Chemis- try cannot be held responsible or liable for its accuracy and completeness, nor for any consequences arising from any errors or the use of the information contained in this pub- lication. The publication of advertisements does not constitute any endorsement by The Royal Society of Chemistry or Authors of any products advertised. The views and opinions advanced by contributors do not necessarily reflect those of The Royal Society of Chemis- try which shall not be liable for any resulting loss or damage arising as a result of reliance upon this material. The Royal Society of Chemistry is a charity, registered in England and Wales, Num- ber 207890, and a company incorporated in England by Royal Charter (Registered No. RC000524), registered office: Burlington House, Piccadilly, London W1J 0BA, UK, Telephone: +44 (0) 20 7437 8656. For further information see our website at www.rsc.org Printed in the United Kingdom by CPI Group (UK) Ltd, Croydon, CR0 4YY, UK Dedication Dedicated to the memory of Prof. George Bodner (08 March 1946–19 March 2021), Purdue University, who inspired so many over decades in their love for organic chemistry education.   Advances in Chemistry Education Series No. 10 Student Reasoning in Organic Chemistry: Research Advances and Evidence-based Instructional  Practices Edited by Nicole Graulich and Ginger Shultz © The Royal Society of Chemistry 2023 Published by the Royal Society of Chemistry, www.rsc.org v Foreword “How do we know what we know?” sounds like a trivial question but it is not. To differentiate between justified belief and opinion has never been more important in the sciences, and especially in the public perception of science in general. This epistemology is one of the pillars upon which sci- ence and all rational action and reasoning is built upon. As the title Student Reasoning in Organic Chemistry reveals, the present book edited by Nicole Graulich and Ginger Shultz analyses the teaching of organic chemistry with the goal to improve chemistry instruction. It therefore fills a long apparent, but never systematically addressed, knowledge gap regarding the outcome of our instructional efforts by highlighting current advances in chemistry edu- cation research. From a very personal perspective, I realize that when I draw an organic reaction mechanism, I hope the students will follow my drawings and my words and it all makes sense. Sometimes I realize that I am not quite sure whether the things I draw are simply memorised to understand the outcome of a reaction—sort of a mnemonic trick—or, if I have reasons to believe that this particular mechanistic hypothesis is close to some “scientific reality”. How hard is it to accept that an electron pair is a curved arrow from which most of the action originates? Can the students visualize chemical structures in three dimensions from some simple stick drawings that are in all honesty quite a leap of faith? Will different representation styles add to the students’ comprehension or confusion? There are many more questions of this sort that are highly relevant but often not discussed. I am pleased to see that the present book picks up where these questions leave me. I’ve spoken to colleagues about this and many feel similarly. Still, there are no systematic efforts to determine whether the applied teaching meth- ods, the language, or the pictorial framework ultimately leads to a deep   Advances in Chemistry Education Series No. 10 Student Reasoning in Organic Chemistry: Research Advances and Evidence-based Instructional  Practices Edited by Nicole Graulich and Ginger Shultz © The Royal Society of Chemistry 2023 Published by the Royal Society of Chemistry, www.rsc.org vii viii Foreword understanding of organic reaction mechanisms that would allow the stu- dents to reason rationally about the outcome of a reaction that they have not yet seen before. I am quite impressed that the present book tackles these issues with a very fresh look, often including very modern assessment tools of students as well as teacher habits and performances. As I teach organic reaction mechanisms myself, this book comes quite handy, and I comple- ment the Editors on their efforts to put such a valuable resource together. I am sure you will benefit from this collection of excellent articles just as much and hope you enjoy the reading! Dr Peter R. Schreiner Liebig-Chair and Professor of Organic Chemistry Justus Liebig University Giessen, Germany President, German Chemical Society (GDCh, 2020 & 2021)