PS5_Solutions - chair conformation). BH 3 then H 2 O 2 ,...

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CHEM 3570, FALL 2008 Problem Set 5 I created a couple of additional problems for testing Chapter 4 topics 1) Show the major product for each of the following reactions. Provide a detailed mechanism for the Br 2 reaction. OH H 2 ,Pd BH 3 then H 2 O 2 , NaOH Br 2 Br 2 , H 2 O m-CPBA Hg(OAc) 2 , H 2 O then NaBH 4 OH OH OH O H H Br OH O O H H O H H Br
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Mechanism: OH Br Br OH Br O H H Br B - H O H H Br
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2) Provide the product of this reaction (you need to draw it as a NICE cyclohexane
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Unformatted text preview: chair conformation). BH 3 then H 2 O 2 , NaOH H i n t : The product is a TRIOL tBu HO OH HO tBu HO OH OH 3) Provide the starting material needed? H 2 , Pd C L U E : The starting material DOES NOT contain ANY chiral carbons!!!!! You will learn in Chem 3580 that this compound is stabilized and cannot be hydrogenated under reasonable reaction conditions...
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PS5_Solutions - chair conformation). BH 3 then H 2 O 2 ,...

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