0243Pb79-09.cwk (WP)

0243Pb79-09.cwk (WP) - simply to craft a decently detailed...

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Problem 79, Chemistry 0243 - 2009 Although cyclohexene undergoes the normal addition reaction with bromine, benzene ( 1 ) does not. Br 2 Br Br Br 2 no reaction 1 Under forcing conditions, benzene will react, but the product does not come from the addition reaction, but from a substitution. The rate of the reaction depends on solvent polarity, so it is still an ionic (not radical) reaction . Br 2 Br 1 "forcing conditions" + HBr (a) Your job is NOT to explain why benzene fails to do the normal addition reaction, but
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Unformatted text preview: simply to craft a decently detailed arrow formalism mechanism for the substitution reaction. (b)Toluene ( 2 ) could, in principle, form any or all of the three products shown. Use your mechanism to predict whether para or meta will be preferred, and explain why. We are NOT asking you to make any predictions about ortho. CH 3 Br 2 CH 3 Br CH 3 Br CH 3 Br "forcing conditions" or or 2 ortho meta para...
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Fall '10 term at NYU.

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