Structure and nomenclature

The simplest of the alkylbenzenes, methylbenzene, is given the special name of toluene. Compounds
containing longer side chains are named by pjefixing the name of the alkyl group to the word -
benzene, as, for example, in ethylbenzene, n-propylbenzene, and isobittylbenzene. The simplest of
the dialkylbenzenes, the dimethylbenzenes, are given the special names of xylenes; we have, then,
o-xylene, m-xylene, and p-xylene. Dialkylbenzenes containing one methyl group are named as
derivatives of toluene, while others are named by prefixing the names of both alkyl groups to the
word -benzene. A compound containing a very complicated side chain might be named as a
phenylalkane (C6H5 = phenyl). Compounds containing more than one benzene ring are nearly always
named as derivatives of alkanes. The simplest alkenylbenzene has the special name styrene. Others
are generally named as substituted alkenes, occasionally as substituted benzenes. Alkynylbenzenes
are named as substituted alkynes.

Physical properties

As compounds of low polarity, the alkylbenzenes possess physical properties that are essentially the
same as those of the hydrocarbons we have already studied. They are insoluble in water, but quite
soluble in non-polar solvents like ether, carbon tetrachloride, or ligroin. They are almost always less
dense than water. As we can see from Table 12.1, boiling points rise with increasing molecular
weight, the boiling point increment being the usual 20-3u 3 for each carbon atom. Since melting
points depend not only on molecular weight but also on molecular shape, their relationship to
structure is a very complicated one. One important general relationship does exist, however,
between melting point and structure of aromatic compounds: among isomeric disubstituted
benzenes, the para isomer generally melts considerably higher than the other two. The xylenes, for
example, boil within six degrees of one another; yet they differ widely in melting point, the o- and w-
isomers melting at -25 and -48, and the/MSomer melting at -f 13. Since dissolution, like melting,
involves overcoming the intermolecular forces of the crystal, it is not surprising to find that generally
the para isomer is also the least soluble in a given solvent. The higher melting point and lower
solubility of a para isomer is only a special example of the general effect of molecular symmetry on
intracrystalline forces. The more symmetrical a compound, the better it fits into a crystal lattice and
hence the higher the melting point and the lower the solubility. Para isomers are simply the most
symmetrical of disubstitutr d benzenes. We can see (Table 12.1) that 1,2,4,5-tetramethylbenzene
melts 85 to 100 higher than the less symmetrical 1,2,3,5- and 1,2,3,4-isomers. A particularly striking
example of the effect of symmetry on melting point is that of benzene and toluene. The introduction
of a single methyl group into the extremely symmetrical benzene molecule lowers the melting point
from 5 to -95. Titik lebur yang lebih tinggi dan kelarutan yang lebih rendah dari para isomer hanya
istimewa contoh efek umum simetri molekuler pada kekuatan intrakristalin.

Senyawa yang lebih simetris, semakin cocok untuk menjadi kisi kristal dan karenanya

semakin tinggi titik leleh dan semakin rendah kelarutannya. Para isomer itu sederhana

benzenes disubstitutr d paling simetris. Kita dapat melihat (Tabel 12.1) bahwa 1,2,4,5-
tetramethylbenzene mencair 85 hingga 100 lebih tinggi daripada yang kurang simetris

1,2,3,5- dan 1,2,3,4-isomer. Contoh yang sangat mencolok dari efek

simetri pada titik leleh adalah benzena dan toluena. Pengenalan a

gugus metil tunggal ke dalam molekul benzena yang sangat simetris menurunkan

titik leleh dari 5 hingga -95.