Clickers in Organic Chemistry
Vincent Maloney
Indiana U. Purdue U. Fort Wayne
Active Learning in Organic Chemistry
Workshop
What is your experience with clickers?
A. Have not tried them
but am interested
B. Use them
occasionally
C. Use them regularly
D. Have not tried them
but am unconvinced
E. Opposed to their
use
43%
25%
21%
en
us
e
4%
th
ei
r
..
se
d
to
bu
t
Op
po
th
em
re
gu
la
ot
tri
ed
th
em
ca
s
oc
th
em
Us
e
Us
e
Ha
v
Ha
v
en
ot
tri
ed
th
em
bu
t
..
io
na
lly
r ly
7%
What barriers prevent you from
adopting clickers?
31%
28%
13%
10%
10%
7%
Co
st
to
Co
st
Ti
s
ud
tt
m
o
en
e
d
to
t
e
pa
le
ar
rtm
n
ne
en
t
w
so
ftw
Lo
ss
...
of
c la
ss
tim
Cl
e
ic k
er
us
Ot
er
he
/n
r
o
ba
rri
er
s
A. Cost to student
B. Cost to department
C. Time to learn new
software or adding
questions
D. Loss of class time
E. Other
F. Clicker user/no
barriers
Resources
• Teaching with Classroom Response Systems by
Derek Bruff, Jossey-Bass, 2009
• Clickers in Action: Active Learning in Organic
Chemistry by Suzanne M. Ruder, Norton, 2013
– Suggested by J. Muzyka
Why Clickers ?
(Student Response Systems)
• Technology for Classroom Assessment
Techniques (CATs)
• Variety of methods for obtaining immediate
feedback of student knowledge and learning
– before any quiz or exam where it’s “too late”
Why Clickers ?
• e.g. Ask a question based on material just
covered in lecture
– Have all students answer
– Quickly check answers
– Correct misconceptions/misunderstanding
Benefits
• Immediate feedback
• All students respond
• Anonymous to students
– Instructor can determine who answered and how
• Improve student learning
• Grading?
Benefits
• Improve student learning
– Thomas D’Angelo and K. Patricia Cross, Classroom
Assessment Techniques: A Handbook for College Teachers,
Jossey-Bass, 1993
– Bruff for clickers
– David C. Haak, et al. Increased Structure and Active
Learning Reduce the Achievement Gap in Introductory
Biology, Science 332, 1213 (2011)
– Louis Deslauriers, et al. Improved Learning in a LargeEnrollment Physics Class, Science, 332, 862, (2011)
– Linda B. Nilson, Teaching at Its Best, Jossey-Bass, 2010, pp.
273 – 280
What are the pedagogical benefits of
using clickers?
61%
39%
Be
de
sc
itu
tte
ra
tt
re
te
nt
io
0%
on
ce
rn
Al
.. .
lo
ft
he
ab
ov
e
of
s..
.
0%
n
of
pr
ov
ed
re
te
nt
io
Im
ov
ed
pr
n
en
ga
g
ov
ed
pr
Im
...
m
em
en
t
0%
Im
A. Improved
engagement
B. Improved retention of
material
C. Improved retention of
students
(course/institution)
D. Better attitudes
concerning course
and material
E. All of the above
Types of question
•
•
•
•
•
Review gen chem
Assess retention of material
Application of concept
Inquiry/discovery-based learning
Check attendance?
Solving problems
• Multi-step synthesis
• Mechanisms
• Spectral interpretation
Question types
•
•
•
•
Multiple choice
Numerical
Text
Sources of questions
– Instructor generated
– Publisher generated
– Student generated
What is the major product of the reaction shown?
A
B
C
D
20%
D
C
8%
B
4%
A
A.
B.
C.
D.
68%
CH
3
How many signals appear in the 13C NMR
spectrum of the compound shown?
96%
Responses
5
4
3
4
Values:
5
Value Matches: 0
Other
5
6
4%
4
Rank
1
2
What kind of isomers are these?
Br
Br
H
H
H
CH 3
30%
CH 3
H
9%
FI
G
er
Ot
h
UR
AT
IO
N
AL
M
ER
S
CO
N
ST
ER
EO
IS
O
DI
AS
TE
RO
M
ER
4%
M
ER
4
STEREOISOMERS
Values:
5
CONFIGURATIO...
Value Matches: 0
6
Other
9%
AS
TE
RE
O
DIASTEREOMERS
DIASTEREOMER
DIASTEROMER
DI
1
2
3
22%
M
ER
S
Responses
AS
TE
RE
O
Rank
26%
trans
DI
cis
How should the mechanism arrows be written? (Write a sequence of
numbers. The 1st number is the base of a curved arrow. The second
number is the head. If there is a second arrow, the 3rd number would
be the base and the 4th number would be the head.
1
H 3C H 2C
3
2
4
S
5
6
C H 2C H 3 + H 3C
8
7
Br
H 3C H 2C
91%
S
C H 2C H 3
CH3
Responses
3678
36
3
4
Values:
5
Value Matches: 0
6
Other
36
78
9%
36
Rank
1
2
B r-
Propose a multi-step synthesis to convert cyclohexene to ethoxycyclohexane.
1 D 2O
2
6 H 2O
7
R an ey N i, E tO H
-
OD
1 1 H 2S O 4, H 2O
HCl
12 N a
4 C l2
9 N aN H 2, N H 3
S O C l2
N
10 C H 3 C H 2 O - , C H 3 C H 2 O H ,
87%
13 C H 3 C H 2 B r
14 P B r 3
Responses
111213
810
3
Values:
4
Value
Matches: 0
5
Other
13%
11
12
13
6
5
81
0
Rank
1
2
8
3 M g, E t 2 O
(Li, T H F )
OH
1 1 H 2S O 4, H 2O
12 N a
O
1 3 C H 3C H 2B r
C H 2C H 3
O-
Synthesize 3-methylhex-3-ene from butan-2-ol and 1-bromopropane by
entering the number for the correct reagents for the letters in the boxes. You
will need to determine what Compounds U, V, and W along the way. Use each
reagent only once.
1. (1. LiAlH4, ether 2. H3O+)
2. Na2Cr2O7, H2SO4
3. Compound V
4. Compound W
5. Ph3P
6. BuLi, ether
7. Mg, ether
8. NaOEt, EtOH
O
H 3C
H2
C
C
CH3
Practices
• Informal peer learning
– Students discuss questions
• How time for questions?
– Varies, ~ 2 min.
– Listen to level of conversation
• What is the minimum number of questions
suggested per 50 min. class period?
– Varies, ~ 3
Practices
• “Good” questions for peer learning
– < 70% correct but >30% correct
– Ask students to discuss with someone who
disagrees and poll again
• Easy questions (>80% correct) often given to
avoid discouragement
• Posting % responses
– Can affect follow up polling
Practices
• Class participation points
– e-mail reason for absence to avoid losing clicker
points
– No grade for % correct
– Grade based on % correct
– Combination of both
Potential Issues
• Choosing same answer as smartest person
nearby
• Random guessing
• “Helping” absent friend
• Exams and quizzes
Logistics
• Options for student use
– Own
– Share
– Rent
– Mobile device
• Integration with PowerPoint
Original Conventional Wisdom
• Use one system across your institution
– Decided by faculty and/ITS
• Mobile devices
– Hardware no longer consideration
– Important considerations
•
•
•
•
Cost
Software
Ease of use
Where does data reside
Drawing Structures
• Mastering Chemistry: Pearson
– Easier to check student responses in class
– Draw structures and vote on them
Acknowledgements
• IPFW
– CELT
– ITS
• Jennifer Muzyka and Centre College