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Answers%20to%20PS6 - Chem 242 Spring 2007 Problem Set 6...

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Chem 242 Spring 2007 Problem Set 6 Question 1. Give the IUPAC name for each of the following compounds. CHO Me Me Me O Me O H Cl CH 3 Cl Me Me O Me O 3-methyl cyclopentanecarboxaldehyde 3-methyl-2-butanone 4,5-dichlorohexanal 6-methyl-2,3-octanedione Question 2. Provide reagents to most efficiently perform the following transformations. CH 3 O H a) b) c) d) CH 3 N Ph H aniline (removal of H 2 O) CH 3 OH H 3 C CH 3 OH H 3 C NH 2 O OH Me Me H 3 C H H 3 C Me 1. Hg(OAc) 2 , H 2 O 2. EtMgBr 1. Hg(OAc) 2 , H 2 O 2. NaBH 4 1. O 3 (any workup) 2. KCN/HCN 3. H 3 O +
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Chem 242 Spring 2007 Question 3. A CH242 student wanted to perform the following reaction for their laboratory synthesis project: H OH H O H O H O BrMg (followed by an H + workup) A Why will this transformation fail? How might you make compound A from benzaldehyde? H O BrMg These functionality are incompatible (they will react with each other) H O H BrMg MeO OMe H OH H MeO OMe H OH H O A H 3 O +
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Chem 242 Spring 2007 Question 4. Provide a mechanism for the following transformation.
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Answers%20to%20PS6 - Chem 242 Spring 2007 Problem Set 6...

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