KeyForExam3 - Name _ W.09.215H Exam No. 3 Page 1 1....

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Name _____________________________________ W.09.215H Exam No. 3 Page 1 OH 1. Complete the following reaction sequences. 1. CrO 3 /H 2 SO 4 2. SOCl 2 3. N NH O Li + Ph O 1. O Li + Ph 2. NH 4 Cl/H 2 O 3. CrO 3 /H 2 SO 4 OSi(CH 3 ) 3 O H 3 CO 1. LiAlH 4 1. H N H 3 C OCH 3 2. PhLi 3. aqueous workup 1. 2. LiAlH 4 3. aqueous workup NH 2. NH 4 Cl/H 2 O 1. NaBH 4 2. NH 4 Cl/H 2 O H excess OSi(CH 3 ) 3 O H Provide the reagents below (number sequential steps) PCC or Swern O N N O Ph O OSi(CH 3 ) 3 O H 3 CO OSi(CH 3 ) 3 HO 1 equiv DIBAL OSi(CH 3 ) 3 O Ph OSi(CH 3 ) 3 N
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Name _____________________________________ W.09.215H Exam No. 3 Page 2 2. The hydrolysis of ester A could proceed by at least two possible mechanisms (I and II, below). Provide two different experiments that you could use to distinuguish between these mechanisms. But sure to completely describe the experiment and predict the expected outcome for each mechanism . You can modify the
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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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KeyForExam3 - Name _ W.09.215H Exam No. 3 Page 1 1....

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