Question #0bff3

1 Answer
Oct 18, 2016

You might get "1,3,5-trinitrobenzene."

Explanation:

Conc. nitric acid and conc. sulfuric acid mixed together form the classic nitrating mixture that delivers the NO_2^+ electrophile:

H_2SO_4(aq) + HNO_3(aq) rarr H_2NO_3^(+) + HSO_4^-

Sulfuric acid protonates nitric acid, which then spits out water and nitronium ion:

H_2NO_3^(+) rarr H_2O + NO_2^(+)

The nitronium ion, which is linear, is a potent electrophile, and will react with nucleophiles such as an aromatic ring.

C_6H_5NO_2 + NO_2^(+) +HSO_4^(-) rarr 1,3-C_6H_4(NO_2)_2 +H_2SO_4.

Another equiv of nitronium ion might give 1,3,5-C_6H_3(NO_2)_3

The nitro group is a "meta-director."