ps7 - the reactions(a and(b profiled below CH 3 CH 3 CH 3...

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Chemistry 3590 Honors Organic Chemistry I PROBLEM SET #7 FALL, 2009 Please answer problems 43, 45, 71 and 80 in Chapter 7 of Bruice ( note: the answers to problems 61 and 68 in the Study Guide contain errors!) and the following questions: (1) How could the following racemic compounds be synthesized using a Diels-Alder reaction? In some cases, additional retrosynthetic analysis might be needed to identify the Diels-Alder “disconnect.” Ph CO 2 CH 3 CH 3 O CH 3 COCH 2 CH 3 H CH 3 O CN CN CN CN H HO (a) (b) (c) (d) (2) Which one of the four constitutional isomers ( W-Z ) of dimethylcyclopentene shown below would give the particular pattern of steroisomers in both
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Unformatted text preview: the reactions (a) and (b) profiled below? CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 W X Y (racemic) Z (racemic) (a) It reacts with excess HBr to form two different racemic mixtures. (b) It reacts with: (i) BH 3-THF; (ii) H 2 O 2 , HO-, H 2 O to form one meso stereoisomer and one racemic mixture. (3) The first attempt to prepare hexaphenylethane by dimerization of the triphenylmethyl radical instead led to the formation of the product Q shown below. Propose a mechanism for this reaction. Why do you suppose hexaphenylethane is not formed? C Ph Ph Ph 2 Ph Ph H Ph 3 C Ph = Ph 3 C–CPh 3 X Q...
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