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A Manual of the Chemistry of the Carbon Compounds

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388 THE CHEMISTRY OF<br />

COMPOUNDS WITH NINE ATOMS OP CARBON.<br />

The compounds <strong>of</strong> this group are derived from <strong>the</strong> following<br />

hydrocarbons :—<br />

Methyl-ethyl-benzeue C « H i { CH^<br />

Propyl-benzene C6H6.C3H7<br />

IsopropyUbenzene or Cumene . . CBH6.CH4 CJT S<br />

Allyl-benzene C6H6,C8H6<br />

TRIMETHYL-BENZENES<br />

ME8ITYLENK, OR 1*3*5 TBIMETHTL-BENZENE<br />

\. 3<br />

Occurs toge<strong>the</strong>r with pseudocumene in coal-tar, and is produced by<br />

acting with sulphuric acid on acetone. Each molecule <strong>of</strong> this coinpound<br />

loses one molecule <strong>of</strong> water, and <strong>the</strong> residues CH3 — C—CH<br />

combine, three metliyl-ethines being condensed to trimethyl-benzene,<br />

just as three niolecnles <strong>of</strong> ethine form one <strong>of</strong> benzene. (See page 318.)<br />

This reaction shows that <strong>the</strong> methyls occupy <strong>the</strong> symmetrical position<br />

1-3-5.<br />

Pure meaitylene is prepared by pouring one volume <strong>of</strong> acetone ou<br />

some sand placed in a retort, and <strong>the</strong>n adding a cold mixture <strong>of</strong> one<br />

volume <strong>of</strong> sulphuric acid and half a volume <strong>of</strong> water.<br />

After 24 hours, <strong>the</strong> mixture is distilled, and <strong>the</strong> distillate purified<br />

by continued fractional distillation. Pure mesitylene is a refractive<br />

liquid, possessing a peculiar smell, and boiling at 168°.<br />

Monochlorotnesitylene C0HaClCCH^$ is a limpid liquid, boiling<br />

QX AUO f<br />

pichloromesitylene CjHCUCH^ crystallizes from alcohol in shining<br />

prisms, melting at. 59°, and boiling at 205°.<br />

fnchloromesiiykne CjCljCCH^g melts at 204°, and sublimes in long<br />

prisms.<br />

These three compounds are formed by <strong>the</strong> action <strong>of</strong> chlorine on<br />

cold mesitylena

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