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.

  • $\begingroup$ Reaction of alkyl with KCN is different from reaction of alkyl with AgCN $\endgroup$ – manshu Apr 26 '16 at 6:35

On treating ethanolic solution of nitroalkane 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.

$$\ce{R-X + AgNO2 -> R-NO2 + AgX}$$

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.

$$\ce{R-X + KNO2 -> R-O-N=O + KX}$$

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    $\begingroup$ But my question is , Is it the only product or the product with higher yield $\endgroup$ – BEWARB Apr 26 '16 at 13:29
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    $\begingroup$ @BEWARB It is the only product. $\endgroup$ – Nilay Ghosh Apr 26 '16 at 13:31
  • $\begingroup$ Can $AgNO_2$ not exist as nitrite-N? $\endgroup$ – User Dec 17 '17 at 4:03
  • $\begingroup$ @Internet Guy no, silver nitrite is nitrite-O as the silver is bonded to oxygen atom. See this: chemistry.stackexchange.com/questions/55300/… $\endgroup$ – Nilay Ghosh Dec 17 '17 at 4:35
  • $\begingroup$ @Nilay Ghosh but the other O has 2 lone pairs, why dosen't it attack the methyl group ...? $\endgroup$ – vishesh jain Jun 18 '19 at 4:10

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