Winter 2007 blank

Winter 2007 blank - Name Page 1(W.07.215.E1p1 I(20 points...

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Name:_____________________ Page 1(W.07.215.E1p1) Cl O Cl TESADH Instead of a single stereoiosmer of Molecule A, mixture of the enantiomers of Molecule A was treated with NaBH 4 . Four different oxiranes resulted from this reaction: Oxirane C and its enantiomer, and Oxirane D and its enantiomer. Draw the oxiranes in the boxes below. Molecue A Enantiomer of Oxirane C Oxirane D a) ( JOC , 2007 , 72 , 30) Using the reagents W110A and TESADH, a single stereoisomer of Molecule A undergoes a completely stereoselective addition of a hydride (without a protonation) to yield alkoxide intermediate B which then forms Oxirane C. Oxirane C b) ( JOC , 2007 , 72 , 139) The reaction shown below froms a new C-C bond. The proposed mechanism for this reaction includes two steps: an electrophilic addition (A E ) followed by an elimination. Draw the two step mechanism. O S S HOBF 3 O S S H 2 OBF 3 + + O S S HOBF 3 + O S S H 2 OBF 3 + W110A Show appropriate stereochemistry at both relevant centers of the alkoxide intermediate B.
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This note was uploaded on 01/28/2011 for the course CHEM 210 taught by Professor Kiste during the Spring '10 term at Michigan Flint.

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Winter 2007 blank - Name Page 1(W.07.215.E1p1 I(20 points...

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