CHEM2211 Exam 3 2008

CHEM2211 Exam 3 2008 - n U\U STRY 2211 XA l J i'l lnrch 26...

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)- w y nU:. \USTRY 2211 [XAl\] J i'llnrch 26. 1008 Be sure to read each question carefully_ Partial credit may b(> as,;gned where appropriate. This test must be laken in pen. Penril emms "ill not he graded. Good lu c k~! L (10 pomts) Consider the carbocations below. !fa carbocmion can rearrange to fonn a more stable carbocation. draw a SInu:mrc for the rearranged carbocation in the bo.~ provided. Ifno rearrangement i. likely wrile "no rearrangement" d (!) TOTAL SCORE .. _-- •. ' -- '--- ;. --- ' - - - 2. (10 points) Viny1cyc1opropanc reacts with HBr 10 yield a rearrallg,'d alkyl bromide. Draw curved arrows 10 show the reaction of vinykyclopropanc wilh HUT to yield the rearranged carbocation. Dr~w the stTUcture of the rearranged carbocatioll intemtediate in brackets, and draw the structure of the final product in the bo.~ . r.> C H- ', cd - - , o
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, 3- (14 points) epi-Aristolochcnc. a hydrocarbon found in both pepper and lobacco, is biosynthesil.ed by the following pathway_ Add curyed arrows 10 show the mechanism of each step.
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  • Spring '07
  • Atwood
  • Trigraph, dd curyed arrows, likely wr il, ore stable carbocation., vinykyclopropanc wilh HUT, rly indkate bolh

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CHEM2211 Exam 3 2008 - n U\U STRY 2211 XA l J i'l lnrch 26...

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