How is benzene nitrated?

1 Answer
Dec 29, 2017

So you want to nitrate benzene....

Explanation:

This is an organic reaction, but it features a nice bit of inorganic chemistry. Specifically, it uses sulfuric acid to protonate nitric acid, and form the nitronium cation, a powerful electrophile that binds to the electron-rich benzene ring....

#underbrace(HOstackrel+N(=O)O^(-))_"nitric acid"+H_2SO_4 rarr HO-stackrel+N(=O)OH+HSO_4^(-)#....

#HO-stackrel+N(=O)OH rarr underbrace(O=stackrel+N=O)_"nitronium ion"+H_2O#

And then...
#O=stackrel+N=O+C_6H_6 rarr {C_6H_6}^(+)NO_2#

#{C_6H_6}^(+)NO_2+HSO_4^(-) rarr C_6H_5NO_2 + H_2SO_4#

The nitric acid/sulfuric acid mix is known as a nitrating mixture...and the benzene ring can be substituted by up to 3 nitro groups, in a #1,3,5# pattern....

Anyway, if you want to do the reaction, you will have to look it up in #"Organic Syntheses"#....it is a classic organic reaction.