How does benzene react with $\ce{NaNO2/HCl}$? Will $\ce{PhNO}$ be obtained? I read that pyridine can be produced under special conditions, but what will happen in some less exotic conditions?

  • $\begingroup$ Afaik, $\ce{NO^+}$-cation is too weak as electrophile to react with benzene, nitrosobenzene is obtained indirectly. $\endgroup$
    – permeakra
    Sep 1, 2014 at 13:40

1 Answer 1


As you noted, the link you provided was to a reaction run under rather exotic conditions (low-temperature plasma). Under more everyday laboratory conditions, for example, in solution, activated aromatic rings can react with $\ce{NO^+}$ as shown below.

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However if there is a ring-activating amino substituent present, then the $\ce{NO^+}$ will react with the nitrogen to produce the synthetically important diazonium ion.

enter image description here


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