Summary of Arene and Aryl Halide Chemistry

S SUMMARY OF ARENE AND ARYL HALIDE CHEMISTRY PREMMTION A. ALKYLBENZENES 

Problem 11.45 Write structural formulas for the principal monosubstitution products of the indicated reactions from the following monosubstituted benzenes. For each write an S or F to show whether reaction is SLOWER or FASTER than with benzene, (o) Monobromination, C HjCF,. (b) Mononitration, CjH5COOCHj. (c) Monochlorination, C HjOCHj. (d) Monosulfonation, C HjI. (e) Mononitration, C HjC H,. (/) Monochlorination, CjHjCN. (g) Mononitration, C HjNHCOCHj. (h) Monosulfonation, CftHjCH(CH3)CH2CHj. 

Problem 11.46 Which xylene is most easily sulfonated  

Problem 11.47 Write structures for the principal mononitration products of (a) o-cresol (o-methylphenol), (b) p-CHjCONHC HjSOjH, (c) w-cyanotoluene (m-toluonitrile).  

Problem 11.48 Assign numbers from 1 for least to 5 for most to designate relative reactivity to ring monobromination of the following groups. 

Problem 11.43 Use PhH, PhMe, and any aliphatic or inorganic reagents to prepare the following compounds in reasonable yields (a) m-bromobenzenesulfonic acid, (h) 3-nitro-4-bromobenzoic acid, (c) 3,4-dibromonitrobenzene, 

Nitration of p-BrC6H4CH3 would have given about a 50-50 mixture of two products 2-nitro-4-bromotoluene would be unwanted. When oxidation precedes nitration, an excellent yield of the desired product is obtained. 

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