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Penn 241quiz2-06 ans - CHEM 241-601 Quiz 2 85 pts November...

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CHEM 241-601 Name_________________________ Quiz 2, 85 pts. November 7, 2006 Signature____________________________ Answer the following questions in the space provided. (point values in parentheses) 1.(15) Consider the molecules 3(S),4(S)-3-bromo-2,2,4,5,5-pentamethylhexane ( A ) and the corresponding 3(S),4(R) ( B ) stereoisomer. These 2 stereoisomers each undergo a stereospecific E2 reaction in hot NaOH to afford two different alkene products . Additionally, one of the stereoisomers reacts 100 times more rapidly than the other. Draw both A and B in their “reactive” conformations (either Newman or saw horse projections) and determine: a) the structures of the 2 products and b) which substrate reacts more rapidly. Briefly explain (your pictures should be most of your explanation). Br * * C C H t Bu CH 3 Br t Bu H Br H t Bu t Bu CH 3 H S S S R H t Bu Br C H CH 3 t Bu C H t Bu CH 3 Br H t Bu C C t Bu CH 3 H t Bu t Bu H C CH 3 t Bu C A B B reacts more rapidly since the reactive conformation is more stabl (and therefore exists a greater % of the time).
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