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

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What barriers prevent you from adopting clickers?

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

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ss o f c la ss ti me Cl ick er u Ot se he r/ r no b ar rie rs 28%

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 Large- Enrollment 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?

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

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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. A B. B C. C D. D

68% 20% A 4% 8% B C D

CH 3 How many signals appear in the 13 C NMR spectrum of the compound shown?

96%

2 3

Rank

1

Responses

5 4 6 Other

5 4% 4

What kind of isomers are these?

Br Br H CH 3 H cis 2 3

Rank

1

Responses

DIASTEREOMERS DIASTEREOMER DIASTEROMER 4 5 6 STEREOISOMERS CONFIGURATIO...

Other trans H H

30%

CH 3

22% 9% 9% 4% DI AS TE RE O M ER S DI AS TE RE O M ER DI AS TE RO M ER ST ER EO IS O M ER S CO N FI GU RA TI ON AL 26% Ot he r

How should the mechanism arrows be written? (Write a sequence of numbers. The 1 st number is the base of a curved arrow. The second number is the head. If there is a second arrow, the 3 rd be the base and the 4 th number would number would be the head.

3 1 2 H 3 CH 2 C S 4 5 CH 2 CH 3 + 6 7 H 3 C 8 Br H 3 CH 2 C

91%

S CH 2 CH 3 Br CH 3 2 3

Rank

1

Responses

3678 36 4

Values:

5

Value Matches: 0

6 Other

9% 36 36 78

Propose a multi-step synthesis to convert cyclohexene to ethoxycyclohexane.

1 D 2 O 6 H 2 O 2 Raney Ni, EtOH 7 OD 8 HCl

Rank

1 2 3 11 H 2 SO 4 , H 2 O 12 Na

Responses

111213 810 3 Mg, Et 2 O (Li, THF) 4 Cl 9 NaNH 2 , NH 3 2

87%

5 3 SOCl 2 CH 2 O , CH 3 N CH 2 OH,  13 CH 3 CH 2 Br 14 PBr 3

13%

6 Other

11 12 13 81 0

13 CH 3 CH 2 Br 11 H 2 SO 4 , H 2 O O CH 2 CH 3 OH 12 Na 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. LiAlH 4 , ether 2. H 3 O + ) 2. Na 2 Cr 2 O 7 , H 2 SO 4 3. Compound V 4. Compound W 5. Ph 3 P 6. BuLi, ether 7. Mg, ether 8. NaOEt, EtOH

H 3 C H 2 C C O CH 3

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