Winter 2006 blank

Winter 2006 blank - Name:_ Page1 (W.06.215.E1.p1) I. (28...

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Name:___________________ Page1 (W.06.215.E1.p1) OH OH HO H 3 CO excess H 2 CrO 4 HCl (a) I. (28 points) Complete the following reaction sequences, including stereochemistry as required. If stereoisomers are formed, draw one isomer and write in the box "+ enantiomer" or "+ diastereomer" 4 4 4 (b) J Org Chem 2005 , 70 10619 O 1) B 2 H 6 , THF 2) NaOH, H 2 O 2 HOCH 2 CH 2 OH C 18 H 30 O 3 Hint: Two functional group transformations take place Jones: CrO 3 H 2 O/ H 2 SO 4 4 4 8 H 2 SO 4 catalytic TsOH 0 o C C 19 H 25 ClO 4 (CH 3 CH 2 ) 3 N CH 3 I
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Name:___________________ Page2 (W.06.215.E1.p2) II. (18 points) (a) J. Am. Chem. Soc. 2006 128 , 199 C OH H C C C OCH 3 O B - C OH C C Compound A Compound D Compound C Compound A is transformed to Compound C. The transformation is catalyzed by a base, B: - . The mechanism includes the intermediate, Compound D . Draw Compound D and the mechanism illustrating the transformation of D to Compound C . You may use HB and B: - for any Bronsted acid and base that you need to use. Compound X N CH 2 SH O S O O HO (b) 8 3 2 O HO H C O OCH 3 Draw both Compund D and the mechansim for forming
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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 2006 blank - Name:_ Page1 (W.06.215.E1.p1) I. (28...

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