Dolbier HW Solutions 573

Dolbier HW Solutions 573 - by a Sandmeyer reaction in which...

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23.19 The reaction of p -bromotoluene with aqueous sodium hydroxide at elevated temperature proceeds by way of a benzyne intermediate. The same benzyne intermediate is formed when p -chlorotoluene is the reactant, and so the product ratio must be identical regardless of whether the leaving group is bromide or chloride. 23.20 Dinitration of p -chloro(tri f uoromethyl)benzene will take place at the ring positions ortho to the chlorine. Compound A is 2-chloro-5-(tri f uoromethyl)-1,3-dinitrobenzene. Tri f uralin is formed by nucleophilic aromatic substitution of chlorine by dipropylamine. Tri f uralin is N , N -dipropyl-4- (tri f uoromethyl)-2,6-dinitroaniline. 23.21 p -Chlorobenzenethiolate reacts with p -nitrobenzyl chloride by an S N 2 process to give compound A. Reduction of the nitro group yields the aniline derivative, compound B. Chlorbenside is then formed
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Unformatted text preview: by a Sandmeyer reaction in which the diazonium ion is replaced by chlorine. CH 2 S O 2 N Cl Compound A 1. Fe, HCl 2. NaOH CH 2 S H 2 N Cl Compound B CH 2 S Cl Cl Chlorbenside 1. NaNO 2 , HCl 2. CuCl 1 CH 2 Cl O 2 N p-Nitrobenzyl chloride CH 2 S O 2 N Cl p-Chlorophenyl p-nitrobenzyl sulfide (compound A) Cl NaS Sodium p-chlorobenzenethiolate CF 3 Cl NO 2 O 2 N 2-Chloro-5-(tri f uoromethyl)-1,3-dinitrobenzene (compound A) CF 3 N(CH 2 CH 2 CH 3 ) 2 NO 2 O 2 N N , N-dipropyl-4-(tri f uoromethyl)-2,6-dinitroaniline (tri f uralin) CF 3 Cl p-Chloro-(tri f uoromethyl)-benzene HNO 3 H 2 SO 4 , heat (CH 3 CH 2 CH 2 ) 2 NH CH 3 Br 1 CH 3 OH m-Methylphenol CH 3 OH p-Methylphenol NaOH, H 2 O 300 8 C CH 3 ARYL HALIDES 667...
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