Answer to Question #176111 in Organic Chemistry for Vikram

Question

Write the product for the reaction of iodoethane with sodium nitrite and silver nitrite. explain why two different types of product are formed.

Answer 1

NaNO2 is predominantly ionic and one of the oxygen atoms has a negative charge. Nucleophilic attack through this negatively charged oxygen atom on the iodoethane mainly gives ethyl nitrite. AgNO2 is a covalent compound and both oxygen and nitrogen atoms carry lone pair of electrons. Nitrogen is less electronegative than oxygen so its pair is more easily available for bond formation. As a result, the product is nitroethane.