Discovery (?) Group Projects in
the Organic Laboratory
Martin B. Jones
Adams State College
Alamosa, CO
Discovery (Guided-Inquiry)
Experiments
• Predetermined outcome (but only the
instructor knows)
• Inductive reasoning required of the students
• Procedure is given by instructor
Domin, D. S. J. Chem. Educ. 1999, 76, 543
Sources of Organic Chemistry
Discovery Experiments
Journal Articles (examples)
Mohan, R. S. and coauthors, 6 papers in J. Chem. Educ. 1999-2005;
Reeve, A. M. J. Chem. Educ. 2004, 81, 1497; Adrian, J. C. Jr; Hull,
L. A. J. Chem. Educ. 2001, 78, 529; Horowitz, G. J. Chem. Educ.
2003, 80, 1039; Moroz, J. S.; Pellino, J. L.; Field, K. W. J. Chem.
Educ. 2003, 80, 1319.
Textbooks (examples)
Pavia, Lampman, Kriz, Engle “Introduction to Organic Lab
Techniques – A Microscale Approach”; Schoffstall, Gaddis,
Druelinger “Microscale and Miniscale Organic Chemistry Lab
Experiments”; Mohrig, Hammond, Morrill, Neckers “Experimental
Organic Chemistry: A Balanced Approach”
History of Chemistry Group
Projects Labs at ASC
• Summer 2000 – ACS Gen Chem workshop
• Fall 2000 – Project Labs implemented in
General Chemistry at ASC
• Fall 2001 – Project Labs implemented in
Organic Chemistry at ASC
• Summer 2002 – Workshop on Organic
Discovery Experiments at BCCE
Group Projects in Organic
Chemistry at ASC
• Fall Semester: Effect of Acid on
Dehydration of 2-Methylcyclohexanol
(adapted from Taber, R. L.; Champion, W.C. J. Chem. Educ. 1967, 44,
620; Moeur, H. P.; Swatik, S. A.; Pinnell, R. P. J. Chem. Educ. 1997,
74, 833.)
• Spring Semester: Directing Influences in
Electrophilic Aromatic Substitution
Reactions (adapted from “Introduction to Organic Laboratory
Techniques – A Microscale Approach”, 3rd Ed. Pavia, Lampman, Kriz,
Engel; Saunders; 1999; Exps 39 & 40)
Common Features of Each Project
• Students get a handout that describes the project in
general, including the rubric I use for grading.
• Groups of 4 preferred.
• Molecular Modeling.
• Two weeks for laboratory work, one additional
week to prepare report.
• One formal report per group; individual duplicate
notebook pages also included.
• Group members evaluate each other and
themselves.
Rubric for Group Lab Report
E
G F
P
Format (5)
Correct
Incorrect
Introduction
(10)
Procedure
(20)
Results (20)
Clear purpose; reactions
shown
Unclear; no reactions
Detailed; observations given;
duplicate pages present
Brief; no observations;
no duplicate pages
Calculations shown;
instrumental and modeling
data included
No calculations,
instrumental data, or
modeling data present.
Discussion
(30)
Clear and based on correct
interpretation of actual
results
Based on incorrect
interpretation of actual
results
Ref’s (5)
Pertinent ref’s cited properly
No ref’s
Readability
(10)
Good organization; <3
spelling/grammar errors
Poor organization; many
spelling/grammar errors
Peer and Self Evaluation Rubric
Score yourself and your team members in each category using Excellent,
Good, Fair, Poor or No participation. Please mark your own name with an
asterisk (*). Be honest when you mark your ratings. If you have any
comments to make, use the space below the rubric.
Evaluation Category
Participation in planning/ design
of experiments
Participation in actual
experiments
Efficiency in completing all data
collection
Participation in discussion of
results
Participation in writing of group
report
Names of Group Members
Peer and Self Evaluation Rubric
Evaluation Category
Names of Group Members
A
B
C
D
Participation in planning/design
of experiments
G,E,E,G
G,E,E,G
G,E,E,G
G,E,G,G
Participation in actual
experiments
G,E,E,E
G,E,E,E
G,E,E,E
G,E,E,E
Efficiency in completing all data P,E,E,E
collection
G,E,E,E
G,E,E,E
G,E,E,E
Participation in discussion of
results
F,E,E,G
G,E,E,E
G,E,E,E
G,E,G,G
Participation in writing of group
report
P,E,G,F
E,E,E,E
G,E,E,E
G,E,G,F
Sum
Scaling Factor
17.9
0.918
19.5
1.00
19.4
0.995
18.7
0.959
Dehydration of 2-Methylcyclohexanol
OH
Acid, heat
+
- H2O
CH3
CH3
• Objectives
• Determine if Zaitsev's rule regarding product
distribution in dehydration reactions is valid.
• Investigate the effect of dehydrating agent on
product distribution and yield in dehydration
reactions.
• Timing of Experiment
• Typically the first non-technique based experiment
in the course
CH3
Directing Influences in EAS
Reactions
• Objectives
• Determine the directing influences of two different
substituents in typical electrophilic aromatic
substitution reactions
• Timing
• Second semester, just prior to discussion of EAS
reactions
Directing Influences in EAS
Reactions
NH
O
NH
O
Br 2, HBr, HOAc
Br
O
O
OCH3
OCH3
HNO3, H2SO4
NO2
“Group” Aspect of the Experiment
SA
A
D
My group worked well together for each
experiment.
5
7
My group worked well together for at least one
experiment.
6
5
I would have preferred to have been assigned
to a group rather than to have selected my own.
2
4
3
I think it’s a good idea to have my peers
evaluate me on my contributions to the project.
5
6
1
My group graded me fairly in the peer and selfevaluation rubric.
8
3
SD
N/
A
1
2
1
1
Selected Comments
• I think peer evaluations are generally good & most
students (at least in a class like this) are honest &
thoughtful.
• Having groups picked for us is good because we
learn to work with new people.
• It’s always easier to work with people you get
along with, rather than being assigned to a group
of people who may or may not work well together.
“Discovery” Aspect of the Experiment
SA
I already knew exactly how the experimental
results would turn out (i.e., product distributions)
prior to conducting the experiment and analyzing
the results.
A
D
3
9
1
The molecular modeling portions of the
experiments helped me predict the outcome of
the experiments.
5
6
Conducting the experiment and analyzing the
results helped me remember Zaitsev’s rule for
dehydration reactions and the directing influence
of different substituents in EAS reactions better
than just looking at reactions written on the
board.
These experiments should be done before any
discussion of dehydration (fall) and EAS (spring)
reactions in the lecture portion of the course.
7
5
1
1.5
7.5
SD
2
N/
A
Selected Comments
• A little discussion should be done so that students
have a clue about what is going on.
• Doing the experiments before could help but I
think it works well either way.
• I believe the experiment should be utilized at
approximately the same time lecture covers the
material. It would better reinforce the concepts
learned.
Experimental Design
SA
A
D
I think it’s a good idea for us to come up
with our own experimental procedure, as we
did in the fall.
4
6
1
I prefer to have the exact procedure spelled
out in the lab text, as it was in the spring.
1
6
5
SD
N/
A
1
Selected Comments
• I like the challenge of coming up with the
procedure. It is also helpful to have some
direction as in the spring. I think a combination of
both would be better.
• I think we learn more when we need to think about
it.
• Designing the experiment is half the fun.
Group Project Report
SA
A
D
SD
I enjoyed writing a formal report in the
format of a journal article.
4
1
6
1
I think it is beneficial for me to write a
formal report in the format of a journal
article.
6
6
10
1
I think we should have just written the report
as a normal report in our lab notebooks.
1
N/
A
Selected Comments
• This was the first time I really took a look at the
journal, since then I have looked at many articles.
In writing a report like the journal I learned how to
effectively read a journal article.
• While I didn’t enjoy the journal format, I think it
is beneficial to learn the scientific journal article
format.
• I don’t enjoy writing formal reports but the
importance of knowing their format supercedes
my laziness
Successful or Not?
• The group projects were nice because it gave a
variation in the schedule so that it never got
monotonous.
• Overall, a well worthwhile and engaging activity.
Would prefer not to do it in groups.
• Sometimes the group projects were frustrating, but
it is also a real life situation. Not only did we
learn from the experiment, but we learned from
each other as well.
Average project score (Fall ’05) – 85.5
Average project score (Spring ’06) – 90.3
Acknowledgements
Chemistry 321 and 322 students at Adams State
College from 2001 to present; especially students
from 2005-2006.
Jerry Bell, Melanie Cooper, and the rest of the
ACS GenChem “team”.
Allen Schofftstall, Barbara Gaddis, Connie
Pitman, and Susan Schelble for a workshop on
discovery experiments at the 17th BCCE.