Haloarenes

Haloarenes are the compounds in which a halogen is attached directly to a benzene ring -- X bonded straight to a ring carbon itself, not to a side chain hanging off the ring (which would instead be a benzylic halide, as covered under Classification, section 14.2). Because the halogen sits on an sp2, aromatic carbon rather than an ordinary sp3 alkyl carbon, haloarenes turn out to behave quite differently from haloalkanes in almost every respect covered in this chapter: their C-X bond is shorter and stronger (section 14.5.2), they resist nucleophilic substitution under norm …