HW15Key - occurs under the indicated conditions fill both...

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Graded Homework Problem #15 – Answer Key Deadline : 3:00 p.m., Monday, 4/7/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. In each part below, predict the structure(s) of the major product(s) that will form when the organic starting material is subjected to the indicated reaction conditions. If two different products are formed, draw both of them, one structure in each box. Be sure to show any stereochemistry clearly and unambiguously in each structure you draw. Remember, stereoisomers are different compounds! If only one product is formed in the reaction, draw it in one of the boxes, and fill the other box with the symbol “X”. If no reaction
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Unformatted text preview: occurs under the indicated conditions, fill both boxes with the symbol “X”. Br 2 , H 2 O + (a) Br H 3 C CH 3 OH H 3 C HO Br CH 3 (enantiomers) anti addition regioselectivity n/a (b) + HCl Cl (achiral) (c) 1) BH 3 2) H 2 O 2 , NaOH, H 2 O + H CH 3 OH H O H H H CH 3 a racemic mixture arises from syn addition of H and OH anti-Markovnikov regioselectivity + (d) 1) O 3 2) H 2 O 2 O O OH (e) + 1) OsO 4 2) NaHSO 3 , H 2 O OH OH (achiral) The fact that dihydroxylation is a stereoselective syn addition does not matter here, since the product does not have any stereoisomers possible!!!...
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