Article

Cite This: J. Chem. Educ. XXXX, XXX, XXX−XXX pubs.acs.org/jchemeduc

Introducing NMR Spectroscopy Using Guided Inquiry and Partial

Structure Templating
Erin M. Kolonko*,† and Kristopher J. Kolonko‡
†
Department of Chemistry and Biochemistry, Siena College, Loudonville, New York 12211, United States
‡
Stewart’s Advanced Instrumentation and Technology Center, Siena College, Loudonville, New York 12211, United States
*
S Supporting Information

ABSTRACT: Strategies for teaching NMR spectral interpreta-

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tion in the undergraduate organic chemistry curriculum are

often faculty-centered and can lead to student reliance on rote
memorization and “guess and check” methods rather than
critical-thinking skills for structure determination. This article
describes a student-focused methodology for the introduction
of NMR spectral interpretation. Guided-inquiry tutorials using
NMR prediction tools were developed to enable students to
investigate the trends and concepts in 13C and 1H NMR
spectral interpretation, with an emphasis on making con-
nections between data and foundational chemical knowledge. A
systematic approach to solving unknown structure problems is
presented, providing a framework for students to organize
spectral data and to build molecules from partial structures. The success of this NMR spectroscopy teaching strategy, which can
be adapted for either laboratory or lecture environments, was demonstrated both in positive student survey responses as well as
in quantitative data showing a significant improvement in exam question scores.
KEYWORDS: Second-Year Undergraduate, Organic Chemistry, Laboratory Instruction, Computer-Based Learning,
Inquiry-Based/Discovery Learning, NMR Spectroscopy

■ INTRODUCTION
Interpretation of NMR spectroscopy data is a key skill taught
in undergraduate organic chemistry courses. In addition to
being one of the most important tools in organic chemistry for
structure determination, it is a unique platform for the
development of critical-thinking skills for undergraduate
students. NMR spectral interpretation is a complex process
in which students must grapple with different aspects of the
data, including the number of signals, chemical shift,
integration values, peak shape, and so on. They then must
organize and digest this information to ultimately link the
spectral data to chemical structure. Gaining experience with
this overall process is important for chemistry majors but also
provides students whose future is outside of the chemical field
with experience evaluating a moderately complex data set to
reach an evidence-based conclusion.
NMR spectroscopy is frequently taught by a direct
instruction method, or faculty-centered approach, in which
information is conveyed directly to students via readings in the
text or lectures followed by worked examples. In contrast,
guided-inquiry-based experiments in the chemistry laboratory
encourage students to apply their foundational knowledge and
then to use critical-thinking skills, which increases student
engagement while still being readily implemented.1 In guided-
inquiry-based methods, students are given a question and
procedure for investigation but must determine the known
© XXXX American Chemical Society and
Division of Chemical Education, Inc.
results through the investigative process.2,3 Guided-inquiry-
based NMR experiments have been presented to illustrate
simple spectral trends for the general chemistry curriculum4−6
and to predict aromatic shift tables in the organic chemistry
curriculum;7 however, a comprehensive introduction to NMR
spectroscopy via a guided-inquiry method has not been
reported.
Regardless of the teaching strategy, NMR theory and 1H
NMR spectroscopy are often introduced at a midpoint in the
semester, followed by 13C NMR spectroscopy, a format taken
by most commonly used organic textbooks.8−16 A notable
exception to this trend is the text by Clayden, Greeves, and
Warren, which introduces 13C NMR spectroscopy in Chapter 3
and 1H NMR spectroscopy at the more traditional midpoint of
the text.17 Similarly, the strategy of introducing 13C NMR
spectroscopy prior to 1H NMR spectroscopy has been gaining
traction in the literature because the carbon spectra are often
much simpler for students to interpret and are less
intimidating.6,18−20
After developing a background understanding of NMR
spectroscopy and spectral analysis, students are expected to
apply these concepts to elucidate an unknown structure given
Received: August 13, 2018
Revised: March 27, 2019
A DOI: 10.1021/acs.jchemed.8b00660
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
spectral data. Experienced chemists generally use a systematic
approach for the interpretation of NMR spectra; however, a
systematic process is often not explicitly taught in introductory
courses. In a study of spectroscopy problem-solving ability,
Cartrette and Bodner21 found that key approaches of
participants that were successful versus unsuccessful in
determining unknown structures from spectral data included
(1) a tendency to approach the problems systematically and
(2) drawing fragments of the structures at intermediate stages
of the process. This approach contrasts with the initial
tendency of students to guess at a whole structure with one
or two pieces of information and then try to match the rest of
the data, or the “guess and check” approach, which often leads
to a waste of time, missed pieces of information, or failure to
reach a logical structure.21
With this background in mind, a new methodology was
developed to restructure how NMR spectroscopy was
introduced and taught in a first-semester organic chemistry
course. Guided-inquiry-based activities were developed to
illustrate the main principles in 1D 13C and 1H NMR spectral
interpretation: number of signals, chemical shift, signal
intensity, and multiplicity. Additionally, a systematic process
was designed for guiding students in spectral analysis using a
defined template for signal analysis, followed by proposing
“partial structures” for each signal. Through this two-fold
approach for introducing NMR spectroscopy, students were
able to build a foundation to be more successful in structure
determination and to expand their critical-thinking skills.
■ STRATEGY AND LEARNING OBJECTIVES
Prior to the adoption of this methodology, spectroscopic
techniques were taught via lectures during the laboratory
period focusing on instrumentation and spectral interpretation,
followed by assigning students graded worksheets with practice
problems. This direct instruction method had several draw-
backs, including lack of student engagement, variation in
instruction from section to section, presentation of an
overwhelming amount of information for students without
time to process concepts, a lack of emphasis on critical
thinking, and indirect correlation with known chemical
concepts, such as structure and bonding. An analysis expressed
by various instructors based on graded work and student
conversations was that academically stronger students were
able to work through the information and devise their own
strategies for NMR spectral interpretation; however, moderate
to weaker students relied on the use of memorized spectral
facts and often employed a “guess and check” method for
determining structures, that is, drawing many possible
structures for a given molecular formula and checking them
against the spectrum. This brute force approach has been
shown to be highly inefficient and often unsuccessful.21 Upper-
level chemistry instructors found that students lacked the
ability to interpret basic NMR spectra in subsequent years and
disliked NMR spectroscopy in general.
To increase overall student understanding of NMR spec-
troscopy, guided-inquiry-based tutorials were used to introduce
the concepts and trends of 13C and 1H NMR spectroscopic
interpretation. The scaffolded nature of the tutorials enables
students to discover the concepts and correlations with known
information while making the learning process accessible and
manageable.22 Students were also encouraged to collabora-
tively work through the tutorials with their peers in the
laboratory section. The tutorials were presented in the
B DOI: 10.1021/acs.jchemed.8b00660
Article
laboratory component of the first semester in a two-semester
organic chemistry sequence. Introducing NMR spectroscopy
early in the organic chemistry sequence reinforces general
chemistry concepts, nomenclature, and organic structure and
provides a building point for the inclusion of spectroscopic
concepts throughout the lecture.23−26
Computer-based NMR prediction tools (Mnova, Mestrelab
Research) were employed to enable students to visualize
spectra without the cost of instrument time, reagents, or
solvents. Spectra are clear of additional peaks such as TMS,
residual NMR solvents, and so on, which is beneficial to
students when they are learning the basics of NMR spectral
interpretation. A computer-based format allows this method-
ology to be used in either a laboratory or a lecture setting.
Students can then use the same software to process and
analyze the NMR spectra throughout the two-semester
sequence and any subsequent advanced courses.
Once students had investigated the trends in 13C and 1H
NMR spectroscopy, they were taught a systematic method for
structure derivation from 1H NMR spectra based on the
generation of a partial structure table. This templated and
systematic approach to solving NMR spectroscopy problems
helped students to organize the complex information into
smaller, manageable pieces. Using this information and other
data, such as molecular formula, IR spectra, mass spectra, or
13
C NMR spectra, students were able to effectively build the
structure from the data.
■
METHODOLOGY
The NMR spectroscopy teaching methods described here were
used in the Organic Chemistry I laboratory curriculum for 2
subsequent years, involving a total of 169 students majoring in
biology (68%), biochemistry (14%), chemistry (9%), or other
sciences (9%). Structural characterization techniques are
taught exclusively in the laboratory portion of the curriculum,
with infrared spectroscopy, mass spectrometry, and 13C and 1H
NMR spectroscopy introduced during the first semester of the
two-semester sequence. Aromatic and 2D NMR spectroscopic
interpretations are introduced during the second-semester
laboratory curriculum. Few of the students had any experience
with NMR spectral interpretation prior to the course.
Mnova and NMRPredict
The Mestrelab Research Mnova software (formerly Mestre-C)
was used as a software platform for the NMR tutorials.27 A
perpetual academic site license includes 1D and 2D NMR
processing, NMRPredict, and mass spectrum plugins for a one-
time cost with the ability to purchase support and update
coverage. The program can be used on Mac, PC, and Linux
systems and is vendor-independent, supporting major file
formats. All students enrolled in the laboratory course are
strongly encouraged to install the software on their laptop
computers, and departmental computers with the software are
also available for student use.
Provided with the basic Mnova suite is an NMRPredict
plugin, which is the tool used to design the guided-inquiry
tutorials for NMR spectral interpretation that allowed each
student to draw structures with the software drawing tools and
predict 1D NMR spectra. Tutorials for both 13C and 1H NMR
spectroscopy were developed using the default settings:
CDCl3, 500 MHz/125 MHz, and Mnova Best predictor. If
desired, additional settings can be fine-tuned for spectrum
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
Figure 1. Predicted 13C NMR spectra for (A) pentane, (B) 2-methylbutane, and (C) 2,2-dimethylpropane. The spectra were used to illustrate
trends in the number of signals and signal intensity. The red prediction labels correspond to the red-labeled carbon atoms in the structures.
prediction including deuterated solvent, resonance frequency,
and prediction algorithm.
Alternatively, the tutorials could be adapted to use several
web-based prediction tools that are currently available at no
cost: nmrdb.org,28 SPINUS-WEB,29 or ChemDoodle Web
Components.30 These resources can be used in a similar
manner as NMRPredict for 13C and 1H NMR spectrum
predictions; however, they do not allow for raw data processing
or for saving or overlaying spectra.
13
C NMR Tutorial
The introduction of 13C NMR spectroscopy and subsequently
1
H NMR spectroscopy was incorporated into a 4-week lab
sequence involving natural product isolation. During the first
week, students were given a 25 min introductory lecture on the
principles of NMR spectroscopy, including nuclear spin and
spin states, chemical environment and shielding, chemical shift
units, and NMR-active isotopes. With instructor guidance,
students worked individually on the 13C NMR tutorial handout
during the downtime of a reflux isolation experiment for ∼1 h
and then finished the tutorial outside of the laboratory period.
The key goals of the 13C NMR tutorial were for students to
derive from trends in predicted 13C NMR spectra:
• the effect of symmetry on the number of signals,
C DOI: 10.1021/acs.jchemed.8b00660
Article
• the effect of the number of symmetric carbons and/or
the number of attached hydrogen atoms on the intensity
of the signal,
• the chemical shift trend for the hybridization of carbon
atoms, and
• the chemical shift trend for the attachment of polar
groups to carbon atoms.
For each concept, students were given IUPAC names in the
tutorial for a series of compounds and drew line-bond
structures on separate pages in the software. The process of
drawing structures into the software from given IUPAC names
reinforced both naming and line-bond drawing skills. Students
then predicted the 13C NMR spectra for each series of
compounds to illuminate specific trends and answered leading
questions to help them to understand why the trends were
observed. For example, the effect of symmetry in the molecule
to the number of NMR signals was determined by predicting
the spectra for the constitutional isomers pentane, 2-
methylbutane, and 2,2-dimethylpropane (Figure 1). The
predicted spectrum indicates the carbon numbers associated
with each peak, which enabled students to derive that (1) the
number of nonequivalent carbon atoms is equal to the number
of signals in the spectrum and (2) the signal intensity
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Figure 2. Superimposed representation of predicted 1H NMR spectra. (A) Predicted spectra of ethane, trimethylamine, dimethyl ether, 1,2-
dichloroethane, and ethanedial. (B) Predicted spectra of di-tert-butyl ether, acetone, dimethyl ether, and ethanedial. Individual spectra were
predicted in Mnova, and the spectra were superimposed in the software to illustrate the trends. Structures in matching colors were added using
ChemDraw to emphasize the trend and do not appear in the Mnova superimposed spectra.

correlates to both the number of equivalent carbon atoms and
the number of hydrogen atoms attached to the carbon atom.
These spectra can be viewed individually or can be overlaid
in the software, allowing students to visualize the differences in
the spectra. In total, students predicted spectra for four series
of compounds, covering the common chemical shift range for
13
C NMR spectra. They then used this information to answer
questions relating chemical concepts to the trends in number
of signals, signal intensity, and chemical shift and to develop a
chart of general 13C NMR shift ranges.
During the second week of the sequence after students had
completed the tutorial, instructors presented a summary
lecture of the trends that were investigated to reinforce the
concepts and answer any student questions. Distortionless
enhancement by polarization transfer (DEPT) 13C NMR
spectral interpretation was presented in this lecture, and
students were assigned a worksheet on 13C NMR spectral
analysis to practice the concepts.
1 compounds from IUPAC names, filled in a data table, and then
H NMR Tutorial
After students had gained a foundation of the concepts of
chemical shift and peak intensity from the 13C NMR tutorial,
the concepts of integration and multiplicity were introduced
using 1H NMR predicted spectra in the second tutorial during
the final 2 weeks of the sequence. During the first laboratory
session, students received an 1H NMR tutorial worksheet.
Students were expected to derive trends and concepts in 1H
D DOI: 10.1021/acs.jchemed.8b00660
NMR spectra from the guided-inquiry activity; no introductory
lecture was provided. With instructor guidance, students
worked individually on the handout during a 2 h Soxhlet
extraction laboratory experiment and then finished the tutorial
outside of the laboratory period. Analogous to the 13C NMR
tutorial, the key goals of the 1H NMR tutorial were for
students to derive from trends in predicted spectra:
• the effect of neighboring electronegative atoms on
chemical shift,
• the effect of carbon hybridization on the chemical shift
of hydrogen atoms,
• how integration values correspond to the number of
symmetric hydrogen atoms, and
• simple first-order coupling patterns (doublet, triplet,
quartet, etc.) based on the number of neighboring
hydrogen atoms.
In the tutorial, students predicted spectra from a series of
answered leading questions to help them to determine the
desired trend or concept. For example, students predicted the
1
H NMR spectra for ethane, trimethylamine, dimethyl ether,
1,2-dichloroethane, and ethanedial, which all have a single 1H
NMR signal, to determine the effect on the 1H NMR chemical
shift due to the presence of electronegative atoms attached
directly to the same carbon (Figure 2A). Subsequently, the
chemical shifts for the hydrogen atoms in ethanedial and
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Journal of Chemical Education Article

Figure 3. Predicted 1H NMR spectra for 1,1,2-tribromoethane (A), 1,1-dibromoethane (B), and bromoethane (C). Figures were modified from the
Mnova output to illustrate the key concept of multiplicity. Atom colors have been adjusted from the default settings, the scales have been removed,
and the signals have been aligned to highlight the differences in multiplicity rather than the differences in chemical shift.

dimethyl ether were compared with those of acetone and di-
tert-butyl ether, respectively (Figure 2B), to illustrate that the
number of bonds between the hydrogen atom and the
electronegative atom affects the magnitude of the downfield
shift.
To investigate the concept of multiplicity, students were
instructed to predict 1H NMR spectra of 1,1,2-tribromoethane,
1,1-dibromoethane, and bromoethane (Figure 3) and to note
the number of signals, chemical shifts, number of hydrogen
atoms on the neighboring carbon, and signal multiplicity. From
this analysis, students were able to derive that the multiplicity
of the signal corresponded to the number of neighboring
hydrogen atoms plus one. To reinforce previously illustrated
chemical shift trends, the change in chemical shift of the
hydrogen atoms due to the addition of bromine can be
highlighted by the instructor or added as a student question to
the tutorial.
During the second week of the sequence, instructors
presented a lecture (∼45 min) overview to (1) summarize
the key concepts from the tutorial, (2) explain how multiplicity
is derived, and (3) discuss more complicated multiplet patterns
(e.g., doublet of doublets). The instructors and students then
worked several problems together as a class using a systematic
partial structure approach, discussed below. After building a
foundation of knowledge from the tutorial, instructors found
that students were able to ask questions and were much more
engaged in the summary lecture.
Partial Structure Analysis
The final goal of this methodology was for students to utilize a
systematic approach to determine unknown structures from
E DOI: 10.1021/acs.jchemed.8b00660
spectra. With this strategy, students first organize 1H NMR
spectral data in a template and then apply the extracted,
tabulated data to generate partial structures that directly relate
to the data (Figure 4). Finally, any additional information (e.g.,
molecular formula and IR, mass, or 13C NMR data) is used
with these pieces to build a complete structure. This process
largely alleviated the tendency of students to try to “guess and
check” structures and reinforced the link between the spectral
information and chemical structure.
The 1H NMR spectrum for C8H10 (ethylbenzene) is used to
illustrate this process (Figure 4). The signal at 1.25 ppm has an
integration value of three, indicating three equivalent hydrogen
atoms, and appears as a simple triplet (1:2:1) pattern. To
determine a partial structure, the integration value is
interpreted first, which indicates a CH3, or methyl unit.31
This segment of the partial structure is circled to show that it
represents the hydrogen atoms from which the signal arises.
Using the n+1 rule and observed multiplicity, the structure of
the adjacent carbon atom(s) is proposed. On the basis of the
observed triplet pattern, the adjacent carbon atom(s) must
contain bonds to two hydrogen atoms. For a methyl unit, the
only possibility is for a CH2 unit as a neighbor. This portion of
the structure is underlined to indicate that the information is
derived from the multiplicity of the signal. Finally, the chemical
shift is used to infer if any neighboring groups are influencing
the hydrogen atoms (e.g., O, N, halogens, carbonyl, etc.).
Because the chemical shift (1.25 ppm) falls in the range of
primary alkyl groups, no additional partial structure informa-
tion can be derived from this signal.
The signal at 2.65 ppm integrates for two hydrogen atoms
and appears as a quartet (1:3:3:1) pattern. From integration
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
Figure 4. Partial structure analysis method can be summarized in
three steps: (1) initial interpretation of each signal (integration,
multiplicity, and chemical shift), (2) tabulation of the data and
proposal of a partial structure for each signal, and (3) connection of
the partial structures to form a full organic structure.
information, assignment of a CH2 unit as the source of the
signals (circled) is warranted. The multiplicity (quartet)
indicates that the CH2 has three hydrogen neighbors on
adjacent carbon atoms. Alone, this information can be
interpreted as either (1) a CH3 on one side and quaternary
carbon (or other atom without attached hydrogen atoms) on
the other side or (2) two adjacent carbon atoms containing
one and two hydrogen atoms, respectively. Finally, the
downfield chemical shift indicates that a deshielding group
(X), likely a carbonyl or aromatic ring due to the chemical
shift, is attached. On the basis of this information and the
presence of only one other signal in the alkyl group region, the
first partial structure option above can be rationally chosen.
The final signal at 7.26 ppm is a multiplet in the aromatic
region that has an integration value of five. During the first
semester course, students are taught to interpret aromatic
signals as one multiplet in which the integration denotes the
number of hydrogen atoms attached to the ring system. Thus,
by using the formula, degrees of unsaturation, and integration,
students are able to interpret the signal as a monosubstituted
benzene ring. In the second semester course, aromatic signals
F DOI: 10.1021/acs.jchemed.8b00660
Article
are more fully analyzed using multiplicity and coupling
constants after aromaticity is covered in the lecture course.
The final step in deciphering the structure is to combine the
partial structures such that the matching parts overlap. To
overlap partial structures, atoms that are circled in one partial
structure should be underlined in the other and vice versa
(Figure 4). Students must use the formula, additional data, and
critical-thinking skills to connect the partial structures that do
not overlap explicitly. This systematic approach is further
illustrated by the worked examples in the Supporting
Information. If students analyze all of the components of the
data (integration, multiplicity, and chemical shift) to derive
partial structures, then it is rare that they are unable to
determine the correct structure when given structures of a
difficulty level in line with introductory organic chemistry
courses. The most common pitfall for students in structure
elucidation is neglecting to incorporate chemical shift
information into the partial structures, which can lead to
incorrect linkages in the final structure (e.g., linking an ester
with the carbonyl and oxygen in reverse positions). On
occasion, there are spectra that could rationally be interpreted
as two possible organic structures based on student under-
standing (e.g., 2-phenylethyl acetate and 4-phenoxybutan-2-
one). Compounds such as these can be used to illustrate that
the identification of a unique structure often requires the
evaluation of characterization data from multiple techniques.
Instructors can choose either to accept any reasonable
structures, given the students’ knowledge base, or to provide
additional data (e.g., mp, mass spectrum, or IR and 13C NMR
spectra), depending on what has been covered in the course.
■ ASSESSMENT
The effectiveness of this strategy for teaching NMR spectros-
copy via guided-inquiry tutorials and partial structure
determination was assessed by (1) an end-of-semester student
survey regarding the laboratory curriculum and (2) a
comparison of student scores on structure elucidation
questions of exams.
At the end of the 2016 and 2017 fall semesters, students
responded to an online, anonymous survey regarding the
laboratory curriculum with response rates of 94 and 92%,
respectively, to give 157 total responses. On the basis of the
survey, over four-fifths of students responded that the 1H and
13
C NMR tutorials and the use of the Mnova software to work
up their own spectra provided “great” help in their learning in
the course (Figure 5). Eighty-five percent of students also
responded that they had made great (52%) or good (33%)
gain in interpreting spectroscopic data to elucidate organic
structures.
The effectiveness of the methodology was also assessed by
comparing exam question scores that focused on NMR
spectroscopy in years prior to and after the introduction of
the MNova tutorials and partial structure strategy. Questions
dealing with structure elucidation by interpretation of 1H and
13
C NMR data for 3 years before (2013−2015) and for 2 years
after (2016−2017) the introduction of the new method were
compared (n = 316 and 168 students, respectively). The data
demonstrate that the median scores (67 ± 1% before and 79 ±
1% after) increased significantly after the introduction of this
approach to teaching spectroscopy. An analysis of the
distribution of scores (Figure 6) indicates that the strategies
discussed herein enabled most students to be largely successful
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education Article

surveys as well as a comparison of exam question scores

indicated that the strategy is an effective means for the
introduction of NMR spectroscopy concepts and structure
determination to the student population at large.

■
*
ASSOCIATED CONTENT
S Supporting Information

The Supporting Information is available on the ACS

Publications website at DOI: 10.1021/acs.jchemed.8b00660.
13
C NMR tutorial (PDF, DOCX)
13
C NMR tutorial key (PDF, DOCX)
1
H NMR tutorial (PDF, DOCX)
1
H NMR tutorial key (PDF, DOCX)
Structure determination example problems (PDF,
DOCX)
Worked example problems (PDF)
Step-by-step guide to creating a partial structure table
(PDF)
Figure 5. Survey response data for NMR-related questions. Representative exam problems (PDF)

(57% had a score of 75% or greater) at interpreting NMR data

and predicting an unknown structure.
■ AUTHOR INFORMATION

■
Corresponding Author
CONCLUSIONS *E-mail: ekolonko@siena.edu.
A novel methodology for introducing undergraduate students ORCID
to NMR spectroscopy and interpretation was developed and Erin M. Kolonko: 0000-0002-9054-6642
implemented. This strategy involved the use of guided-inquiry Kristopher J. Kolonko: 0000-0003-4001-7133
tutorials utilizing computer-based prediction tools in Mnova Notes
NMR processing software to enable students to predict series
The authors declare no competing financial interest.

of spectra designed to illuminate NMR spectroscopy trends
and concepts. Students investigated both 13C and 1H 1D NMR
spectra, with the less complex 13C NMR spectra introduced
first. After the introduction of 13C and 1H NMR spectroscopy,
students were taught a systematic approach for the
determination of an unknown organic structure from spectral
data. This approach provides a template for students to
organize the 1H NMR data and determine partial structures for
each signal. The methodology guides students to more
efficiently and effectively determine an unknown structure
using a systematic process. Assessment through student
■
ACKNOWLEDGMENTS
We thank Thomas Hughes, Hilary Hofstein, Hans Reich, and
Daniel Wherritt for helpful conversations, Pablo Monje for
technical assistance with the prediction tools, and the Organic
Chemistry laboratory faculty and instructors at Siena College
who have taught with the curriculum and provided valuable
feedback. We also thank Information Technology Services at
Siena College for funding to purchase and maintain the Mnova
NMR processing software.

Figure 6. Exam data before (orange) and after (blue) implementation of the methodology. The distribution of student NMR spectroscopy-based
question scores is shown along with the median values (vertical lines). The median scores on NMR-based structure identification problems
increased significantly after the introduction of the tutorials and partial structure strategies (nbefore = 316, nafter = 168; standard error (SE = SD/√n)
is reported).

G DOI: 10.1021/acs.jchemed.8b00660
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Journal of Chemical Education

■
Article

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H DOI: 10.1021/acs.jchemed.8b00660
J. Chem. Educ. XXXX, XXX, XXX−XXX