Nitration of Arenes
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What electrophile is involved in the nitration of benzene?
Nitronium ion, NO₂⁺
What mechanism is used in the nitration of benzene?
Electrophilic substitution
What reagents are used to generate the nitronium ion, NO₂⁺?
Concentrated nitric acid (HNO₃) and concentrated sulfuric acid (H₂SO₄)
At what temperature does the nitration of benzene take place, and why at this temperature?
60°C, to ensure mononitration and prevent further substitution
What happens if a higher tempertaure is used during nitration?
A second nitro group may be substituted onto the benzene ring
Write the equation for the formation of the electrophile, nitronium ion, NO₂⁺
2H₂SO₄ + HNO₃ → NO₂⁺ + 2HSO₄⁻+ H₂O
Why is sulfuric acid described as a catalyst in nitration? (H+ reg. - no use)
The H+ is regenerated when it reacts with HSO₄⁻ to reform H₂SO₄, so it is not used up.
Draw the overall equation for the reaction
Outline the mechanism for the nitration of 1- methylbenzene
One use of nitrated arenes?
Manafacture of explosives
How does an existing side group affect nitration of a benzene ring?
The nitro group can substitute at different positions on the ring
What can nitrobenzene be reduced to?
Phenyl amine
What are the reagents used in the reduction of nitrobenzene into phenyl amine?
Reagents: Hot tin (Sn) + concentrate HCl
What are the conditions used in the reduction of nitrobenzene into phenyl amine?
It is heated in a mixture under reflux