W-Chlorotoluene

Note See also w-Chlorotoluene or Benzyl Chloride, Vol 2,p B95-R, for other derivs... 

The spectra of the intermediate transients formed in the reaction of OH with dichloro- and dibromo-benzenes and chloro- and bromo-toluenes exhibited absorption maxima around 325-330 nm with both ortho- and w to-isomers of dichlorobenzenes, dibromobenzenes, and bromotoluenes (Fig. 6). The transients were assigned to the isomeric OH adducts formed from the addition of OH to the benzene ring. A blue shift was observed in the absorption maximum of -bromotoluene (315 nm) when compared to its ortho- and meta-isomers which have maxima at 330 nm. Such a behavior was also seen in the absorption spectra of OH adducts of 0- and w-chlorotoluenes (325-330 nm) and w-xylenes (326-328 nm) as compared to their... 

When w-chlorotoluene is treated with sodium amide in liquid ammonia, the products of the reaction are o-, m-, and />-toluidine (i.e., 0 CH3C6H4NH2, OT-CH3C6H4NH2, and />-CH3CeH4NH2). Propose plausible mechanisms that account for the formation of each product. 

---