# How to identify the aromatic compound with the sum formula C7H6Cl2?

An aromatic compound (A), $$\ce{C7H6Cl2}$$, gives $$\ce{AgCl}$$ on boiling with alcoholic $$\ce{AgNO3}$$ solution and yields $$\ce{C7H7OCl}$$ on treatment with $$\ce{NaOH}$$. (A) on oxidation gives a mono-chlorobenzoic acid which affords one mono-nitro derivative. Find the Compound (A).

Here from $$\ce{C7H6Cl2}$$ we can say it is a benzene derivative. Now as only one chlorine atom reacts with $$\ce{AgNO3}$$, one chlorine atom is directly connected to benzene and one is connected to methyl group which is connected to benzene. But how to find where the $$\ce{-CH2Cl}$$ is situated, i.e. ortho, meta or para?

• Well ! Which chlorobenzoic acid can react with nitric acid and afford only one nitro-derivate ? Think a while ! It is not difficult ! Feb 15 at 20:06
• Well ! para-chlorobenzoic acid is the only possible solution. The nitro group will be attached next to the Cl atom, and that is the only reasonable possibility. Feb 15 at 20:48
• Then what is the problem with ortho product Feb 16 at 4:58
• No problem ! This is the consequence of the electrophilic attack on the benzene ring already substituted. You should know these rules about ortho-, para- or meta- substitutions. I will not develop them here. Feb 16 at 11:18