Question

Choose the correct statement(s) among the following when treatment of $C{H}_{3}C{H}_{2}Br$ with $KN{O}_2$ and $AgN{O}_2$ is done:

• A. The major product will be ethyl nitrite in case of $KN{O}_2$
• B. The major product will be nitroethane in case of $KN{O}_2$
• C. The major product will be ethyl nitrite in case $AgN{O}_2$
• D. The major product will be nitroalkane in case $AgN{O}_2$

Answer 1

Answer: (A), (D)

The major product will be nitroalkane in case $AgN{O}_2$

$KN{O}_2$ 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​.
$C_2{H}_{5}Br+AgN{O}_2\to \underset{\text{Ethylnitrite (Major)}}{C_2{H}_{5}N{O}_2}+\underset{\text{Nitroethane (Minor)}}{C_2{H}_{5}ONO}$

Hence, (a) and (d) are correct.