A Manual of the Chemistry of the Carbon Compounds

348 TEE CHEMISTRY OF
More than seven atoms of chlorine cannot be introduced into
toluene, as, by the further action of chlorine upon the last substitution-products,
the molecule is decomposed with the formation of
hexachlorobenzene,
1*4 Monochlorotoluene is formed by the direct action of chlorine
upon toluene, and the isomefic 1*3 compound has been obtained from
toloidine, which is first converted into acetoluide, and the latter treated
by chlorine. The chlorinated compound yields, on boiling with
alkalis, monochlortolaidine, which is converted into a diazo-compound
and the latter decomposed by absolute alcohol;—
CCHSC11 NJO4H + C 2 H *-OH « C6H4CLCH8 + K2 + HjSO4 + C,H4O
When bromine-vapour is passed into boiling toluene, substitution
takes place only in the methyl group, and the first product formed is
benzyl bromide C6H6.CH2C1, but by acting with bromine on toluene in
the cold two isomeric bromotoluenes are produced,
14 Bromotohiene forms rhombic, colourless crystals, melting at
28-5°, and boiling at 181°.
1*3 Bromotoluene is a liquid which does not crystallize at a low
temperature, and boils at 181°.
By the further action of bromine on toluene in the cold, dibromotolume
C0H8Br2.CHg is obtained, a crystalline solid, melting at 180",
and boiling at 245°.
Iodine substitution-produots of toluene have been obtained from
the three isomeric amldotoluenes by converting them into diazo-compounds,
and decomposing the latter with hydriodic acid
1-2 lodololuene and 1*3 lodotohime are liquids, both boiling at
204°, whilst 1*4 lodotolmne crystallizes In shining, thin plates,
melting at 35°, and boiling at 211°'5.
NITRO-SVBSTOTTION-PRODUCTS,
ffltrotoluenes (LH^NQ^CHg.—By dissolving toluene ia fuming
nitric acid, and adding water to the solution, a heavy oily liquid,
resembling nitrobenzene, is obtained, which ia a mixture of two
isomerides; they may be separated by continued fractional distillation.
1*4 Nitrotoluene crystallizes in colourless prisms, melting at 54°,
and boiling at 237°. By oxidizing it with dilute nitric acid, it is
converted into paranitrobenzoic acid.
1*2 Nitrotoluene is a liquid which does not solidify in a freezing
mixture, and boils at 223°; boiling dilute nitric acid has hardly any
action on it
1*3 Nitrotolwne has been produced by converting 1*4 amidotoluene
into a nitro-amidotolnene, which was transformed into a
diazo-compound, and the latter decomposed fry alcohol. It forms