Dolbier HW Solutions 568

Dolbier HW Solutions 568 - 662 ARYL HALIDES (b) Only one...

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( b ) Only one benzyne intermediate is possible, leading to two products in a 1:1 ratio. D refers to 2 H (deuterium). 23.14 ( a ) o -Chloronitrobenzene is more reactive than chlorobenzene, because the cyclohexadienyl anion intermediate is stabilized by the nitro group. Comparing the rate constants for the two aryl halides in this reaction reveals that o -chloro- nitrobenzene is more than 20 billion times more reactive at 50 ° C. ( b ) The cyclohexadienyl anion intermediate is more stable, and is formed faster, when the electron-withdrawing nitro group is ortho to chlorine. o -Chloronitrobenzene reacts faster than m -chloronitrobenzene. The measured difference is a factor of approximately 40,000 at 50 °
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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