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HW6key - Sessler CH310M/318M Homework Problem Set 6 Due...

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Sessler CH310M/318M Homework Problem Set 6 Due Friday March 11th, 2011 Circle the section in which you are enrolled: 310M 318M Please write the first three letters of your last name in the above boxes Name:___________ TA ____________________ UT EID:___________ TA001 __________________ Signature:_________ TA ___________________ Grade ( + / - / 0 ):______________________ K E Y
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Sessler CH310M/318M Homework Problem Set 6 Due Friday March 11th, 2011 1. Starting from 1-methyl-1-cyclohexene draw the resulting products formed from each set of reaction conditions. Include stereochemistry where appropriate. Br 2 HCl HNO 3 , H 2 O 1. Hg(OAc), H 2 O 2. NaBH 4 1.BH 3 2. H 2 O 2 , KOH 1. OsO 4 2. NaHSO 3 , H 2 O Pd/C H 2 1.O 3 2. H 2 O 2 O O OH Cl OH OH OH OH OH Br Br Br Br OH H OH H OH 2. Explain why is there no stereochemical preference in the products of reactions that utilize a carbocation intermediate in one or two sentences. Draw a carbocation intermediate to support your claim. What is the hybridization of the carbon with the positive charge? There is no stereochemical preference via this type of mechanism because a carbocation intermediate is sp 2 hybridized and thus flat.
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