Question

4.35 Indicate the main monosubstitution products in each of the following reactions. Keep in mind that certain substituents are meta directing and others are ortho,para directing. a. anisole +bromine (Fe catalyst) b. nitrobenzene chlorine (Fe catalyst) c. bromobenzene concentrated sulfuric acid (heat) + SO d. toluene + chlorine (Fe catalyst) e. benzenesulfonic acid + concentrated nitric acid (heat) (H,SO, catalyst) f. iodobenzene + chlorine (Fe catalyst) g. toluene + acetyl chloride (AICl, catalyst) h. ethylbenzene + concentrated nitric acid (H,SO, catalyst)

Answer 1

Ring activating groups directs the incoming electrophile to ortho and para positions Ex:-NH2, -OR, -NR2, -OH, alkyl and halides Ring deactivating groups direct the incoming electrophile to the meta position Ex :-NO2,-SO3H,-CHO,-COOH,-CF3, etc. OCH OCH OCH3 anisole ortho bromo anisole para bromo anisole NO NO CI nitrobenzene meta-chloronitrobenzene SO2H H2SO4 SO bromobenzene So3H CH CI Cl toluene SO,H so,H HNO H,504 234 NO benzenesulfonic acid meta-nitrobenzenesulfonic acid Cl iodobenzene Cl

CH CH3 O CHa CH3COCI CH AICI toluene Et Et Et HNO3NO2 H,504 ethylbenzene NO2