Reaction of an alkyl halide with silver nitrite I want to know that whether both alkyl nitrite and nito alkane are produced or if nitroalkane is the only product. There are many different (contradicting) things written in different books that is confusing me.
On treating ethanolic solution of haloalkane with silver nitrite ($\ce{Ag-O-N=O}$), nitroalkane is formed because since the bond between $\ce{Ag-O}$ is covalent, the lone pair on nitrogen acts as an attacking site for nucleophilic substitution.
$$\ce{R-X + AgNO2 -&gt; R-NO2 + AgX}$$
But on the other hand if haloalkane is treated with potassium nitrite ($\ce{KNO2}$), alkyl nitrite is formed as major product because since the bond between $\ce{K-O}$ is ionic in nature, the negative charge on oxygen serves as an attacking site.
$$\ce{R-X + KNO2 -&gt; R-O-N=O + KX}$$