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Exam2_Honors_Test_Run_Key

Exam2_Honors_Test_Run_Key - 242a Honors Organic Chemistry...

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242a Honors Organic Chemistry Exam II October 4 th 2007 Ghosh 1 Name: John McMurry 1. ( 15 points ) Predict the products of the following reactions. Show relative stereochemistry (only one stereoisomer ) where appropriate. Bonus: ( 3 points ) Provide a name for any three reactions shown above, such as hydroboration. 2. ( 15 points ) Provide the starting material, products or reagents for the following reactions. Hydroboration H O H O O H O H H OH OH H OH H H H OH H H B 1. OsO 4 2. NaHSO 3 , H 2 O 1. O 3 2. Zn, H 3 O + CH 2 I 2 , Zn(Cu) Ether HIO 4 H 2 O 1. BH 3 , THF 2. H 2 O 2 , OH - 1. Hg(OAc) 2 , H 2 O 2. NaBH 4 Oxidative Cleavage Simmons-Smith Reaction 1,2-dihydroxylation Ozonolysis/reduction Oxymercuration Hydroboration/oxidation δ+ δ−
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242a Honors Organic Chemistry Exam II October 4 th 2007 Ghosh 2 Bonus: ( 6 points ) Draw the intermediate that leads to the ketone ( A ) shown above. What is the rearrangement of the intermediate to the final product called? Provide a mechanism.
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