Exam_1-_Winter_2008_blank_copy

Exam_1-_Winter_2008_blank_copy - W08_ Exam 1 Blank Copy I....

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W08_ Exam 1 Blank Copy 1 A) ( JACS , 2006 , 128, 8128) Geosim is the volatile compound responsible for the characteristic smell of freshly turned soil. Identify the following information about geosim. I. (22 points) OH CH 3 CH 3 i) How many 13 C NMR signals? ii) How many stereoisomers does geosim have? iii) Geosim will reaction with Cr +6 to produce a color change. ( circle one ) True or False iv) Write the IUPAC name for geosim: geosim B) ( JOC, 2008 , 73, 2) O O OH OH Excess CH 3 OCH 2 Cl ((CH 3 ) 2 CH) 2 NCH 2 CH 3 (base) C) ( 2007 , 72, 9991) O H O O C H CH 3 Li 1) 2) H 3 O + (protonation) How many stereoisomers of B are possible? Compound B (no stereocheistry needs to be shown) D) ( 2007 , 8478) PCC CH 3 O O O E) ( 2007 , 9046) SCF 2 Br + CH 3 Si CH 3 H 3 C Cl Mg, THF (solvent) + MgBrCl Complete the following reaction sequences, including stereochemistry as required. 2 2 2 4 3 2 1 3 3 H
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W08_ Exam 1 Blank Copy 2 A) ( JOC, 2008 , 73, 517) The transformation of Reactant L to Product M takes place as follows: The oxirane oxygen coordinates to the diisobutyl aluminum hydride f ollowed by assisted ionization to open the oxirane, which gives a resonance-stabilized carbocation in the 4-membered ring (see Intermediate J, drawn in the space below). Then, an intramolecular hydride addition takes place where the hydride adds from the less
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This note was uploaded on 03/21/2009 for the course CHEM 215 taught by Professor Gottfried during the Winter '08 term at University of Michigan-Dearborn.

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Exam_1-_Winter_2008_blank_copy - W08_ Exam 1 Blank Copy I....

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