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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?

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  • $\begingroup$ Afaik, $\ce{NO^+}$-cation is too weak as electrophile to react with benzene, nitrosobenzene is obtained indirectly. $\endgroup$ – permeakra Sep 1 '14 at 13:40
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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.

enter image description here

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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