F.08.215.FE_blank - N ame Page 1 F 08 215F E P1 I 42 poi...

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Name _______________________ Page 1 F.08.215FEP1 I. (42 points) A. Provide the step-wise, curved arrow mechanism for the following ( OL 2007 , 9 , 385). OCH 3 H 3 CO O Cl OCH 3 H 3 CO O O OCH 3 O OCH 3 O H 3 CO O OCH 3 Na B . Provide the step-wise, curved arrow mechanism for the following ( JACS 2002 , 124 , 11975). CH 3 (CH 2 ) 14 C O OH + CH 3 (CH 2 ) 14 OH CH 3 (CH 2 ) 14 C O O(CH 2 ) 14 CH 3 H-B acid catalyst 9 33 + H 2 O
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Name _______________________ Page 2 F.08.215FEP2 II . (39 points) Isomaltose is a disaccharide found in beer, honey, and other natural products. The IUPAC name for isomaltose is - D -glucopyranosyl-(1->6)- - D -glucopyranose. A. Complete the following as required ( JOC 2007 , 72 , 4953). B. O H CH 3 O O C (H 3 C) 3 C C(CH 3 ) 3 1) CH 3 CH 2 MgB r 2) H 3 O + protonation draw one of the product stereoisomers provide oxidation reaction conditons that will not interfere with the ketal The following reaction is observed to give a mixture of aldol reaction stereoisomers. Draw one of them ( OL 2007 , 9 , 421). C. N O (H 3 C) 3 CO H O OCH 3 H O CH 3 + B Cl 3 D. Name this: CH 3 (CH 2 ) 14 C O O(CH 2 ) 14 CH 3 6 6 6 6 8 7 (catalyst)
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Name _______________________ Page 3 F.08.215FEP3 II I.
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