Dolbier HW Solutions 571

Dolbier HW Solutions 571 - 665 ARYL HALIDES 23.17 Reaction...

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23.17 Reaction of a nitro-substituted aryl halide with a good nucleophile leads to nucleophilic aromatic substitution. Methoxide will displace f uoride from the ring, preferentially at the positions ortho and para to the nitro group. 23.18 ( a ) This reaction is nucleophilic aromatic substitution by the addition elimination mechanism. The nucleophile, , displaces chloride directly from the aromatic ring. The product in this case was isolated in 57% yield. ( b ) The nucleophile, hydrazine, will react with 1-chloro-2,4-dinitrobenzene by an addition elimination mechanism as shown. The nitrogen atoms of hydrazine each has an unshared electron pair and hydrazine is fairly nucleophilic. The product, 2,4-dinitrophenylhydrazine, is formed in quantitative yield. ( c ) The problem requires you to track the starting material through two transformations. The F rst of these is nitration of
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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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