There are several aromatic compounds with the formula #C_8H_9Cl#. What are three that have a disubstituted ring where the chlorine is not attached to the ring?

1 Answer
Truong-Son N.
Aug 14, 2016

They have to be the ortho/meta/para isomers. "Not attached to the ring" only means not directly attached. It does not mean you have a chlorine atom somewhere, floating freely next to the compound.

Ortho (same side) means a 1,2 relationship between two aromatic substituents, meta means 1,3, and para (opposite sides) means 1,4.

A default aromatic ring is benzene, #"C"_6"H"_6#, so consider #"C"_6"H"_4# by default for a disubstituted aromatic ring without substituents and go from there. With two carbons and 5 hydrogens available, and the chlorine not directly on the ring...

  • We can have #-"CH"_2"Cl"# as one substituent and #"CH"_3# as the other. This accounts for the remaining #"C"_2"H"_5# in the formula.
  • We can move one of substituents around for the isomers.

Convince yourself that the formulas are still #"C"_8"H"_9"Cl"#. These are respectively called:

  • o-chloromethyltoluene
  • m-chloromethyltoluene
  • p-chloromethyltoluene
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