2008_Exam_3_Answer_Key

2008_Exam_3_Answer_Key - Organic Chemistry c3046y 3rd Hour...

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3rd Hour Exam Organic Chemistry c3046y Wednesday, April 9, 2008 Prof. Leighton Answer Key
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Name: Page 1 1. Predict the products of the following reactions, and provide a mechanism for their formation. b. (10 pts) (Indicate stereochemistry for this one.) a. (10 pts) 1. KH, Δ O 2. H 3 O + Me O OSiMe 3 Me 1. Δ 2. H 3 O + H H O O O H 3 O + H + OH Tautomerize O O H Me Me H Me 3 SiO O H Me Me H Me 3 SiO Me 3 SiO O Me Me HO O Me Me Enantiomer OK as well.
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Page 2 Name: 2. Predict the major product(s) of the following reactions: a. (10 pts) b. (10 pts) 1. i. O 3 ; ii. Zn 2. CF 3 CO 2 H 3. 2 equiv NaBH 3 CN, H + HN O O t -Bu O OBn BnO BnO O OBn O BnO "I + " PhSO 2 NH 2 AgBF 4 N O NH BnO BnO OBn PhSO 2 O OBn HO BnO
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Name: Page 3 3. Provide the reagents necessary to accomplish the following transformations (more than one step required): a. (10 pts) b. (10 pts) (Hint: two different kinds of rearrangement reactions are involved here. ..) CH 2 OH O H OH H H HO OH H HO H CH 2 OH O H HO OH H HO H H O Me Me N CH 3 O OMe O H 1. H 2 NOH 2. H 3 C O O CH 3 O NaOAc 3. NaOMe, MeOH (
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2008_Exam_3_Answer_Key - Organic Chemistry c3046y 3rd Hour...

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