Student Reasoning in Organic Chemistry: Research Advances and Evidence-based Instructional Practices

384 Pages·2023·18.246 MB·English

by  Graulich N., Shultz G. (ed.)

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
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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
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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)
Preface
Eliciting, Supporting, and Assessing Reasoning
Reasoning is a critical aspect of chemistry that students must learn to
become full participants in the discipline. However, reasoning is inherently
complex and science education researchers have struggled to consistently
define and, consequently, to capture patterns of reasoning in student dis-
course and coursework. We seek to understand reasoning to move beyond
the teaching of chemistry as a disconnected set of ideas and to improve the
outcomes of chemistry instruction. In chemistry broadly, we have examined
various types of reasoning that are distinctive of our discipline such as math-
ematical reasoning,1,2 reasoning with chemical representations,3,4 mechanis-
tic reasoning,5–7 and argumentation.8–10 Organic chemistry as a subfield of
chemistry requires reasoning that is distinct from other subfields. We know
that typical organic chemistry instruction often fails to effectively promote
reasoning and relies on assessments that emphasize rote memorization
rather than an understanding of underlying phenomena. This recognition
has led to an emerging focus on reasoning in organic chemistry that is cap-
tured in the chapters of this book including studies examining the role of
representations, in-depth studies of complex reasoning, classroom teaching
practices designed to promote reasoning, and approaches to the formative
assessment of reasoning.
The first section of the book covers research on student representational
competence. Understanding and interpreting visual complex representa-
tions is a primary challenge in organic chemistry learning. The contribu-
tions highlight how using representations in learning are perceived and

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
ix
x Preface
understood by students. While solving organic chemistry tasks students
often struggle to understand the underlying meaning of reaction mecha-
nisms and electron-pushing formalism. Little is known about what students
visually focus on while evaluating the plausibility of reaction mechanism
and how that relates to the types of features they discuss in their reason-
ing. Weinrich & Britt make use of eye-tracking, followed by think-aloud inter-
views, to examine how students visually focus on curved arrows and how
this relates to the students’ mentions of explicit and implicit features of the
given representation. The study demonstrates eye-tracking technology as a
valuable tool to examine how a feature (e.g., curved arrows) is focused on
while evaluating reaction mechanisms and how these insights can be used
to derive implications to support students’ mechanistic reasoning [Section
A, Chapter 1]. Keller & Habig qualitatively investigate if students working on
tasks involving stereochemistry and pericyclic reactions with augmented-re-
ality support incorporated spatial aspects into their explanations compared
to those working without augmented-reality [Section A, Chapter 2]. Learners
who used the augmented-reality app tend to be able to involve spatial aspects
in their reasoning more often and were able to conduct rotation operations
correctly compared to the control group. The work by Ward, Rotich, Hoang &
Popova draw on the seminal work from Kozma and Russel (1997) and com-
bined it with Schönborn and Anderson’s model (2008) to characterize how
organic chemistry students interpret, translate, generate, and use dash-wedge
diagrams and Newman projections [Section A, Chapter 3]. This work demon-
strates that the appropriateness of student reasoning can vary across tasks
focusing on different representations, different representational compe-
tence skills, and whether the student attends to the external features or the
conceptual information embedded in the representation.
The second selection of contributions highlights approaches to describe
student reasoning about reaction mechanisms expressed in written or verbal
contexts. Various frameworks have been used in the last decades that cover
aspects of causality and mechanistic reasoning. The chapters in this section
illustrate an in-depth analysis of students being engaged with organic chem-
istry tasks, argumentation, and in-class discourse. Crandell & Cooper pro-
vide a synthesis of their research on causal mechanistic reasoning as they
have applied it, a description of evidence-based strategies used to engage
students in reasoning and modelling, and findings from two longitudinal
studies [Section B, Chapter 4]. The longitudinal studies both compare stu-
dents in traditional introductory courses to those in CLUE courses, designed
to elicit causal mechanistic reasoning. Their findings speak to the impor-
tance of instruction that is designed to elicit reasoning. Deng, Carle & Flynn
illustrate an argumentation framework focusing on reasoning, granularity,
and comparisons to characterize students’ arguments in organic chemistry
and make use of a constructive alignment approach to guide teaching and
assessment [Section B, Chapter 5]. The third chapter by Asmussen, Rodemer,
Eckhard & Bernholt investigates undergraduate students’ verbal explana-
tions to a series of case comparisons on nucleophilic substitution reactions