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![Page 1: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/1.jpg)
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Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation
Questions.
Julie B. Ealy and Jim Hermanson
Penn State University
Berks-Lehigh Valley
American Chemical Society
Anaheim, CA – March 2004
![Page 2: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/2.jpg)
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Multiple Molecular Images in Organic Chemistry
• CD – 3D molecular images that can be manipulated
• Molecular modeling software
• Physical ball and stick models
• Textbook – ball and wire; space filling; line drawings; “wedge” images
• Online images that can be manipulated
![Page 3: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/3.jpg)
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Cognitive Theory of Multimedia Learning
• Mayer, 2001 - material presented in both pictorial and verbal form
• Process pictures and words in sensory memory visually and auditorily – promotes active engagement in learning – contributes to transfer of knowledge
• Assessment through use of molecular images and questions not previously encountered in class
• Was there a transfer of knowledge?
![Page 4: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/4.jpg)
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Cyclohexane Quiz
![Page 5: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/5.jpg)
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Hydrogen 1 and 2
![Page 6: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/6.jpg)
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Rank: most eq to least eq
![Page 7: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/7.jpg)
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Ranking of structures C & D – preference for equatorial
![Page 8: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/8.jpg)
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Explanation of ranking
Explanation scored as correct or incorrect
n Mean
15 1.286
12 1.182
35 1.471
Overall mean = 1.370
ANOVA = 1.798 p = .175
![Page 9: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/9.jpg)
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Explanation: ranking, correct
• 59.68% (37) - Branch group larger: more hydrogens, more atoms
• 17.74% (11) - More room needed, larger groups cause more crowding
• 12.90% (8) – Stability: more stable if farther away from cyclohexane
• 12.90% (8) – Strain: the larger the molecule the more steric strain; more carbons and hydrogens on C – there is more steric hinderance
![Page 10: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/10.jpg)
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Explanation: ranking, correct
• 6.45% (4) – Repulsion: larger groups exert more repulsive forces
• 4.84% (3) – Electron cloud: Since C has more electrons, it would prefer the equatorial position where it can be further away
• 1.61% (1) – Energy: Groups such as C and D have large electron clouds and molecules containing these groups are most energetically stable when the groups are far apart from other atoms
![Page 11: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/11.jpg)
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Explanation: ranking, incorrect
• 29.03% (18) – Double bonded: harder for it to get where it wants to be; has no rotational ability; locked into place by pi bonds
• 8.06% (5) – Stability: D is more stable; C is more stable; C & D are more stable than A & B
• 6.45% (4) – Energy: more in C; more in C & D; D wants lower energy
![Page 12: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/12.jpg)
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Explanation: ranking, incorrect
• 6.45% (4) – NC: D would want to be closer due to sp2 orbital of C more readily than C’s sp3 orbital of carbon
• 4.84% (3) – Strain: The steric hinderance is not as great with a double bond.
• 3.23% (2) – Branch group larger
• 1.61% (1) – Repulsive forces and Electron cloud
![Page 13: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/13.jpg)
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Stereoisomer Quiz
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Representation of the structures
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If stereoisomers, then…
![Page 16: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/16.jpg)
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Explanation – If stereoisomers, then why?
Explanation scored as correct or incorrect50.00% correct (7) 3, no responseMean = 1.500Correct responses50.00% (7) – different spatial arrangement42.86% (6) – same formula21.43 % (3) – same structure21.43% (3) – mirror images
![Page 17: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/17.jpg)
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Explanation: stereoisomers, correct
• They are stereoisomers because they have the same formula and same structure except the OH groups on the 2nd and 3rd carbons could not possibly be manipulated to match each other without breaking any bonds
• Same molecular formula, same connectivity, different spatial arrangements
![Page 18: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/18.jpg)
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Explanation: stereoisomers, incorrect
• Compounds are mirror images of each other (incomplete)
• These images are not a mirror reflection of each other, although they have the same molecular formula. The H’s off of C-2 in the first picture are in the axial position, one equatorial in picture 2.
![Page 19: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/19.jpg)
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Equivalence Quiz
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Unique carbons?
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Equivalent sets of hydrogens?
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Explanation – structure A
• Scored as correct or incorrectMean = 1.500 n = 14Correct, 50 %, (7)
- equivalent sets of hydrogens were listed by number; one student circled the 3 equivalent sets- There are 3 equivalent sets of hydrogen. There are 3 different environments in which hydrogens occur. Because of the double bond this occurs.
![Page 23: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/23.jpg)
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Explanation – structure A, incorrect
a. 29.57% (4) – 1, 2, 3, 4, grouped as one set and 5, 6 grouped as a second set
b. 7.14% (1) – unclear answer
Carbons 1, 2, 3, and 4 have sets of 2 H
c. 14.29% (2) – no response
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Reactivity Quiz
![Page 25: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/25.jpg)
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Order of increasing reactivity
![Page 26: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/26.jpg)
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Alkyl halide description
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Transfer of knowledge?
• Equatorial vs. axial* Yes – greater than 60% responded correctly on the three quiz questions
• Stereoisomers* Yes – identification of molecular images as stereoisomers - > 76%41% identification of molecules as enantiomers50% explanation of images as stereoisomers
![Page 28: 1 Assessment of Organic Chemistry Students Utilizing Molecular Modeling Images: Quiz Results of Multiple Choice and Explanation Questions. Julie B. Ealy.](https://reader035.fdocuments.us/reader035/viewer/2022062806/5697c02d1a28abf838cd9733/html5/thumbnails/28.jpg)
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Transfer of knowledge?
• Equivalence quiz
* No – 0% - uniqueness of carbons – no axis of symmetry created difficulty
Yes - equivalent sets of hydrogens >57% - axis of symmetry
Explain hydrogen sets – 50%• Reactivity
* No – 37 % - perhaps attributed to reacting substances
Yes – 100% - identification of 1o, 2o, 3o
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Further Study
• Write new multiple choice questions• Rewrite some existing multiple choice questions
utilizing students’ conceptual errors• Write alternative fixed response questions
(Johnstone & Ambusaidi, 2001) utilizing students’ conceptual errors
• Rewrite multiple choice questions based on ambiguity
• Continue to increase sample size