JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3099
Two sequences are carried out on bromoethane. Sequence I: KCN in aqueous ethanol, then boiling with dilute HCl. Sequence II: AgCN in ethanol (covalent, N-bonded reagent), then warming with dilute HCl. Select the correct statements.
AIn sequence I the nitrogen atom of cyanide is the nucleophilic site that bonds to the ethyl carbon.
BSequence I finally gives propanoic acid (as ammonium chloride is also formed).
CSequence II finally gives propanoic acid, since both cyanide reagents form a C-C bond.
DSequence II finally gives ethylammonium chloride and methanoic (formic) acid.
Answer: B, D
Ionic KCN attacks through carbon: CHX3CHX2BrCHX3CHX2CN, and acid hydrolysis of the nitrile gives CHX3CHX2COOH with NHX4Cl. AgCN is covalent, so the lone pair on nitrogen is used and the isocyanide CHX3CHX2NC forms. Isocyanides are hydrolysed by dilute acid (not alkali) to a primary amine salt and methanoic acid: CHX3CHX2NC+2HX2OCHX3CHX2NHX2+HCOOH. Hence the first two statements are correct.