For each of the following compounds, indicate the ring carbon that would be nitrated if

Chapter 19, Problem 62

(choose chapter or problem)

For each of the following compounds, indicate the ring carbon that would be nitrated if the compound is treated with HNO 3 /H 2 SO 4 : a. NO2 COOH b. O C C O CH3 O O CH3 57. Show how the following compounds could be synthesized from benzene: a. m -chlorobenzenesulfonic acid b. m -chloroethylbenzene c. m -bromobenzonitrile d. 1-phenylpentane e. m -bromobenzoic acid f. m -hydroxybenzoic acid g. p -cresol h. benzyl alcohol i. benzylamine 58. How many electrophilic aromatic substitution products are obtained from the chlorination of a. o -xylene? b. p -xylene? c. m -xylene? 59. Arrange the following groups of compounds in order from most reactive to least reactive toward electrophilic aromatic substitution: a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole b. 1-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, 1-methyl-2,4-dinitrobenzene c. toluene, p -cresol, benzene, p -xylene d. benzene, benzoic acid, phenol, propylbenzene e. p -methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p -chloromethylbenzene f. bromobenzene, chlorobenzene, fl uorobenzene, iodobenzene 60. What are the products of the following reactions? a. + HNO3 CH3 O O C H2SO4 b. 1. Mg/Et2O 2. D2O Br CH3 c. + O 1. AlCl3 2. H2O O O OCH3 d. N + Br2 e. 1. Br2, hn 2. Mg/Et2O 3. ethylene oxide 4. HCl CH3 f. FeCl3 Cl + 2 CF3 c. OCH3 Cl d. OH COOH e. C Br O CH3 f. OH CH3 g. CH3 NO2