Exam2Key - 1. Complete the following two reaction...

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Name _____________________________________ W.09.215H Exam No. 2 Page 1 O Si 1. 2. 3. OH 1. H 2 /Pd/BaSO 4 quinoline 2. TsCl, pyridine 3. NaBr/acetone 1. OsO 4 2. NaOH 2. MgBr 3. aq. NH 4 Cl (acidic workup) 1. NaH 3. NaF, H 2 O OH O O Si Si 2. CH 3 I O OCH 3 + diastereomer + diastereomer O O OCH 3 + 1. CrO 3 , HCl, N 1. DMSO, Cl Cl O O 2. N + enantiomer O O (PCC) 1. Complete the following two reaction sequences. 1a. 1b. 6 4 4 4 4 2 NaH (or other strong base) Br NaF, H 2 O (or other fluoride source) Br O O Si Si OH OH HO OCH 3 O catalytic H + OH O
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Name _____________________________________ W.09.215H Exam No. 2 Page 2 2a. The Pinner reaction involves the conversion of nitriles like A to imino ether salts like B . The mechanism for this reaction is very similar to those that you have seen in class for carbonyl additions. Provide a complete arrow pushing mechanism for this transformation. Use H–B for an acid and B for a base when necessary. Ph C N HCl, CH 3 OH N O Ph H H Cl ( A ) ( B ) O NaOCH 2 CH 3 CH 3 CH 2 OH O O 2b. The Favorskii rearrangement involves the conversion of cyclopropanones like C to esters like D . The mechanism for this reaction starts with a carbonyl addition. Provide a complete arrow pushing mechanism.
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This note was uploaded on 02/23/2010 for the course BIO 172 taught by Professor Clark during the Winter '08 term at University of Michigan.

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Exam2Key - 1. Complete the following two reaction...

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