What is the product obtained when ethyl bromide is treated with silver nitrite () in aqueous ethanol?
Answer and explanation
Correct answer: A. Nitroethane
- Step 1: Silver nitrite () possesses predominantly covalent silver-oxygen bonds: .
- Step 2: Because the oxygen atom is covalently bonded to silver, its nucleophilicity is significantly muted; the unshared electron pair on the nitrogen atom acts as the primary nucleophilic center.
- Step 3: Backside attack of the nitrogen lone pair on ethyl bromide expels bromide to yield nitroethane () as the major organic product.
Answer
Nitroethane ().
Why not the others: Ethyl nitrite is the major product obtained with ionic alkali metal nitrites such as ; Ethanamine is obtained by Gabriel phthalimide synthesis or ammonolysis; Ethanol is obtained by hydrolysis with aqueous alkali.
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