W_08_215_E1_key - Name:_KEY_ Page 1(W.08.215.E1p1) I. (22...

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Name:______KEY_______________ Page 1(W.08.215.E1p1) 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) O O CH 3 OCH 2 O OCH 2 OCH 3 12 7 (1S,2R,6S)-1,2-diethyl-2,6-dimethylcyclohexanol 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? OH O O 4 Compound B (no stereocheistry needs to be shown) D) ( 2007 , 8478) CH 3 O O OH 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 S F F Si CH 3 CH 3 CH 3 Complete the following reaction sequences, including stereochemistry as required. 2 2 2 4 3 2 1 3 3 H
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Name:______KEY_______________ Page 2(W.08.215.E1p2) 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 hindered face of the 4-membered ring. Finally, a protonation to remove the aluminum results in Product M.
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W_08_215_E1_key - Name:_KEY_ Page 1(W.08.215.E1p1) I. (22...

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