23.17Reaction of a nitro-substituted aryl halide with a good nucleophile leads to nucleophilic aromaticsubstitution. Methoxide will displace fuoride from the ring, preferentially at the positions ortho andpara 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 productin 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 fairlynucleophilic. The product, 2,4-dinitrophenylhydrazine, is formed in quantitative yield.(c)The problem requires you to track the starting material through two transformations. The Frstof 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.