Monday, May 27, 2019

organic chemistry - Nitrosation of benzene


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?



Answer



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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