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.

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    $\begingroup$ Reaction of alkyl with KCN is different from reaction of alkyl with AgCN $\endgroup$
    – manshu
    Apr 26, 2016 at 6:35

1 Answer 1


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.

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

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, 2016 at 13:29
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    $\begingroup$ @BEWARB It is the only product. $\endgroup$ Apr 26, 2016 at 13:31
  • $\begingroup$ Can $AgNO_2$ not exist as nitrite-N? $\endgroup$
    – User
    Dec 17, 2017 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/… $\endgroup$ Dec 17, 2017 at 4:35
  • $\begingroup$ @Nilay Ghosh but the other O has 2 lone pairs, why dosen't it attack the methyl group ...? $\endgroup$ Jun 18, 2019 at 4:10

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