2002 Final Key

2002 Final Key - Name_KEY_ ID # _ Organic Chemistry 2301...

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Name__________________KEY__________________ Chem 2301, Spring 2002, Final Exam, Page 1 ID # ____________________________________ Organic Chemistry 2301 Spring 2002 Final EXAM 350 Points 15 Pages plus tables 1) 10 points __________________ 2) 20 points __________________ 3) 20 points __________________ 4) 20 points __________________ 5) 30 points __________________ 6) 20 points __________________ 7) 30 points __________________ 8) 30 points __________________ 9) 30 points __________________ 10) 30 points __________________ 11) 30 points __________________ 12) 30 points __________________ 13) 25 points __________________ 14) 25 points __________________ Total 350 points __________________ Average 237 SD 61 Count 177
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Name__________________KEY__________________ Chem 2301, Spring 2002, Final Exam, Page 2 High 340
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Name__________________KEY__________________ Chem 2301, Spring 2002, Final Exam, Page 3 1. (10 points) Draw a Lewis dot structure for each of the following molecules; show all lone pairs. Indicate the hybridization at all atoms except hydrogen. (a) CH 3 CN H C H H C N sp3 sp (b) CH 3 COCH 2 CH 3 H C H H O H H C H H H sp3 sp2 sp3 sp2 C C 2. (20 points) The structure below is related to molecules observed in interstellar space and may have interesting electrical conducting properties. (a) Give the molecular formula for the above molecule. C 10 H 12 (b) Indicate the number of pi bonds and the number of sigma bonds in this molecule. 21 sigma bonds
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Name__________________KEY__________________ Chem 2301, Spring 2002, Final Exam, Page 4 5 pi bonds
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Name__________________KEY__________________ Chem 2301, Spring 2002, Final Exam, Page 5 3. (20 points) Consider the molecule 2,3-dimethyl butane shown below. 2,3-dimethyl butane (a) Looking down the C2-C3 bond, draw a Newman projection for the highest energy conformer. Use one of the templates provided. H 3 C H CH 3 CH 3 CH 3 H (b) Looking down the C2-C3 bond, draw a Newman projection for the lowest energy conformer. Use one of the templates provided. CH 3 H CH 3 CH 3 H H 3 C (c) Looking down the C2-C3 bond, draw a Newman projection for the lowest energy eclipsed conformer. Use one of the templates provided. H 3 C H CH 3 H CH 3 H 3 C (d) Is there more than one possible answer to the question in part (c)? If so, explain why. Present your answer in terms of eclipsing, gauche and anti interactions.
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Name__________________KEY__________________ Chem 2301, Spring 2002, Final Exam, Page 6 Yes, there are two 2 eclipsed conformers with same energy. In each case, they have one CH3-CH3 eclipsing interaction and two CH3-H eclipxing interactions.
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Name__________________KEY__________________ Chem 2301, Spring 2002, Final Exam, Page 7 4. (20 points) Identify the functional groups indicated by the arrows. Carbonyl is
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2002 Final Key - Name_KEY_ ID # _ Organic Chemistry 2301...

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