2000 Final Exam Key

2000 Final Exam Key - Name_KEY_ ID # _ Organic Chemistry...

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Name___________________KEY_________________ Chem 2301, Fall 2000, Final Exam, Page 1 ID # ____________________________________ Organic Chemistry 2301 Fall 2000 Final EXAM 350 Points 13 Pages plus tables 1) 20 points __________________ 2) 10 points __________________ 3) 25 points __________________ 4) 15 points __________________ 5) 15 points __________________ 6) 30 points __________________ 7) 30 points __________________ 8) 30 points __________________ 9) 30 points __________________ 10) 30 points __________________ 11) 30 points __________________ 12) 30 points __________________ 13) 30 points __________________ 14) 25 points __________________ Total 350 points __________________ Average 227 SD 58
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Name___________________KEY_________________ Chem 2301, Fall 2000, Final Exam, Page 2 Count 149 High 343
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Name___________________KEY_________________ Chem 2301, Fall 2000, Final Exam, Page 3 1. (20 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 CO 2 H H C H H C O O H sp3 sp3 sp2 sp2 (b) CH 3 CH 2 CHCCH 2 C H H H C H H C H C C H H sp2 sp2 sp sp3 sp3 2. (10 points) Consider the molecule shown below. CH 3 C1 C2 C5 C4 CH 3 H 3 C Use one of the Newman projection templates given below to show the most stable conformation of the above compound around the C4-C5 and C2-C1 bonds. Set up your drawing looking down the C4-C5 and C2-C1 bonds. Note: this means C4 and C2 are closer to you than C5 and C1.
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Name___________________KEY_________________ Chem 2301, Fall 2000, Final Exam, Page 4 CH 3 H CH 3 H H H CH 3 H C4-C5 Bond C2-C1 Bond H CH 3 H H 3 C CH 3 H H H C4-C5 Bond C2-C1 Bond 2 axial and 1 equatorial methyl groups, higher energy conformer 2 equatorial and 1 axial methyl group, lowest energy (most stable) conformer
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Chem 2301, Fall 2000, Final Exam, Page 5 3. (25 points) The structure of testosterone, a male specific hormone (androgen) is shown below. O Testostrone OH (a) How many chiral carbons are present in testosterone? O Testostrone OH Chiral carbons (*) * * * * * * 6 chiral carbons (b) Determine the absolute configuration ( R or S ) of the chiral center indicated in testosterone. O
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2000 Final Exam Key - Name_KEY_ ID # _ Organic Chemistry...

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