Textbook Question
What products would you expect from the following coupling reactions?
(d)
(e)
19. Reactions of Aromatics: EAS and Beyond
Benzene Reactions
Multiple Choice
Which set of reagents is required to synthesize nitrobenzene from benzene?
A
Concentrated and concentrated
B
Chlorine () and aluminum chloride ()
C
Acetyl chloride () and aluminum chloride ()
D
Bromine () and iron(III) bromide ()
Verified step by step guidance1
Identify the type of reaction needed to convert benzene to nitrobenzene. This is an electrophilic aromatic substitution where a nitro group (-NO\_2) is introduced onto the benzene ring.
Understand that nitration of benzene requires generating the nitronium ion (NO\_2\^+), which acts as the electrophile in the reaction.
Know that the nitronium ion is formed by mixing concentrated nitric acid (HNO\_3) with concentrated sulfuric acid (H\_2SO\_4). The sulfuric acid protonates nitric acid, leading to the loss of water and formation of NO\_2\^+.
Write the key equilibrium for the generation of the nitronium ion:
\(\$\$\mathrm{HNO\_3 + H\_2SO\_4 \rightleftharpoons NO\_2^+ + HSO\_4^- + H_2O}\)\$\$
Conclude that the correct reagents for nitration of benzene to nitrobenzene are concentrated sulfuric acid and concentrated nitric acid, which together generate the electrophile needed for substitution.
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