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Nitration of Benzene

The document summarizes the nitration of benzene reaction. Benzene reacts with a mixture of concentrated nitric acid and sulfuric acid at 50°C or less to form nitrobenzene. The sulfuric acid acts as a catalyst by generating the reactive nitronium ion from the reaction of nitric acid and sulfuric acid. This nitronium ion is the electrophile that undergoes electrophilic substitution when it attacks the benzene ring, adding a nitro group to form nitrobenzene.

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171 views3 pages

Nitration of Benzene

The document summarizes the nitration of benzene reaction. Benzene reacts with a mixture of concentrated nitric acid and sulfuric acid at 50°C or less to form nitrobenzene. The sulfuric acid acts as a catalyst by generating the reactive nitronium ion from the reaction of nitric acid and sulfuric acid. This nitronium ion is the electrophile that undergoes electrophilic substitution when it attacks the benzene ring, adding a nitro group to form nitrobenzene.

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usman
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The Nitration of Benzene

The Nitration of Benzene


This page gives you the facts and a simple, uncluttered mechanism for the electrophilic substitution reaction between benzene and a
mixture of concentrated nitric acid and concentrated sulfuric acid.

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The electrophilic substitution reaction between benzene and nitric acid
Benzene is treated with a mixture of concentrated nitric acid and concentrated sulfuric acid at a temperature not exceeding 50C. As
temperature increases there is a greater chance of getting more than one nitro group, -NO2, substituted onto the ring. Nitrobenzene is
formed:

\[ C_6H_6 + HNO_3 \rightarrow C_6H_5NO_2 + H_2O\]

or:

The concentrated sulfuric acid is acting as a catalyst.

The formation of the electrophile


The electrophile is the "nitronium ion" or the "nitryl cation", \(NO_2^+\). This is formed by reaction between the nitric acid and the
sulphuric acid.

\[ HNO_3 + 2H_2SO_4 \rightarrow NO_2^+ 2HSO_4^- + H_3O^+\]

The electrophilic substitution mechanism


Stage one

Stage two

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Contributors
Jim Clark (Chemguide.co.uk)

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