CH 310N POW-8_key - for racemic mixtures and “meso”...

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CH 310N – POW #8 Williams Fall 2010 Due: 8 AM, Tues Oct. 26, 2010 1 Name (print): ____________________________________________________________ Signature: _______________________________________________________________ Do Homework In Pen Please write the first three letters of your last name in the boxes
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CH 310N – POW #8 Williams Fall 2010 Due: 8 AM, Tues Oct. 26, 2010 2 1. Complete the following transformations by providing the missing reactants or products. Specify relative stereochemistry where appropriate, and write “racemic” for racemic mixtures, and “meso” when a meso compound is produced. (3 pts). CH 3 H 3 C CH 3 O 1. B 2 H 6 2. H 2 O 2 , NaOH H 3 C CH 3 H O 1. MgBr 2. H 3 O + H 3 C CH 3 OH HO HO Racemic Ph 3 P CH 2 HgSO 4 , H 2 SO 4 H 2 O H 3 C CH 3 H 3 C CH 3 OH PCC or PDC CH 3 CH 3 OH racemic 1. OsO 4 2. NaHSO 3 OR OsO 4 (cat.) H 2 O 2
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CH 310N – POW #8 Williams Fall 2010 Due: 8 AM, Tues Oct. 26, 2010 3 2. Provide complete structures for the reagents or products as needed to complete the following transformations. Show stereochemistry where relevant, and write “racemic”
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Unformatted text preview: for racemic mixtures, and “meso” when a meso compound is produced. (3 pts) O O Br OH NaOH, Dioxane I 1. LDA 2. MeI 2. BuLi or NaH Br 2 , H 2 O O H 2 C PPh 3 1. PPh 3 racemic O O O OEt O EtO racemic B) A) H O O α, β-unsaturated ketone NaH, EtO O O OEt NaOH heat CH 310N – POW #8 Williams Fall 2010 Due: 8 AM, Tues Oct. 26, 2010 4 3. Provide the appropriate reagents or products as necessary to complete the following transformations (4 pts). H 3 C CH 3 H 3 C Cl NaO t Bu HO t Bu a) O Br 2 (excess), KOH H 2 O, heat b) Ph CH 3 O Ph O Br c) O O d) CH 3 CH 3 O CH 3 racemic H 3 C H 3 C CH 3 O Br Br Br Br Br 2 , CH 3 CO 2 H H 2 O, heat 1) LDA, THF warm 2) H 3 C O Cl CH 310N – POW #8 Williams Fall 2010 Due: 8 AM, Tues Oct. 26, 2010 5 SCORE : _______________ /10 O OH O OH OH O e) NaOH, H 2 O f) O g) 1) CH 3 CH 2 ONa CH 3 CH 2 OH (CH 3 CH 2 ) 2 O 2) NaOH, H 2 O heat O CH 3 O 1) NaBH 4 2) H + /H 2 O H 3 C O CH 3 O CH 3 O...
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CH 310N POW-8_key - for racemic mixtures and “meso”...

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