Question

Choose the correct statements among the following when treatment of $C{H}_{3}C{H}_{2}Br$ with $KN{O}_2$ and $AgN{O}_2$ is done.
I. The major product will be ethyl nitrite in case of $KN{O}_2$.
II. The major product will be nitroethane in case of $KN{O}_2$.
III. The major product will be ethyl nitrite in case $AgN{O}_2$.
IV. The major product will be nitroalkane in case $AgN{O}_2$.

• A. I and II
• B. II and III
• C. I and IV
• D. III and IV

Answer 1

The correct option is C I and IV

$KN{O}_2$ is predominantly ionic.​ It exists as free ions in solution. O site is more nucleophilic than N site and available to attack the ethyl chloride. Hence, the major product will be ethyl nitrite.

$C_2{H}_{5}Br+KN{O}_2\to \underset{\text{Ethylnitrite (Major)}}{C_2{H}_{5}ONO}+\underset{\text{Nitroethane (Minor)}}{C_2{H}_{5}N{O}_2}$
Ag-O bond in $AgN{O}_2$ is predominantly covalent Since, N site is more nucleophilic than O site and available to attack the ethyl chloride​. Hence, lone pair of N attacks the ethyl chloride and nitroethane is formed as major product​.
$C_2{H}_{5}Br+AgN{O}_2\to \underset{\text{Ethylnitrite (Major)}}{C_2{H}_{5}N{O}_2}+\underset{\text{Nitroethane (Minor)}}{C_2{H}_{5}ONO}$
Hece option c is correct.