Trichlorotoluenes are
organochlorine compounds
Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds that contain one or more carbon–chlorine bonds. The chloroalkane class (alkanes with one or more hydrogens substituted b ...
, in particular
aryl chloride
In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, bro ...
s, with the formula . Six
constitutional isomer
In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...
s exist, differing in the relative position of the three chlorine
substituent
In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule.
The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...
s around the ring. All isomers colorless and lipophilic solids.
Preparation and use
Four trichlorotoluenes—the 2,3,4-, 2,3,6-, 2,4,5-, and 2,4,6- isomers—are produced in significant yields by treatment of toluene with three
equivalents of chlorine in the presence of various
Lewis acid
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any ...
s.
These isomers result from the usual
selectivity
Selectivity may refer to:
Psychology and behaviour
* Choice, making a selection among options
* Discrimination, the ability to recognize differences
* Socioemotional selectivity theory, in social psychology
Engineering
* Selectivity (radio), a ...
of
electrophilic aromatic substitution
Electrophilic aromatic substitution (SEAr) is an organic reaction in which an atom that is attached to an aromatic ring, aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitut ...
reactions of substituted benzenes.
2,3,6-Trichlorotoluene is a precursor to
2,3,6-trichlorobenzoic acid (2,3,6-TBA), a commercial herbicide.
Related compounds
*
Dichlorotoluene Dichlorotoluenes are organochlorine compounds, in particular aryl chlorides, with the formula . Six constitutional isomers exist, differing in the relative position of the two chlorine substituents around the ring. They are all colorless and lipop ...
References
{{Reflist
Toluenes
Chlorobenzene derivatives
Multiple compounds, tabular