MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / SN1 vs SN2: substrate, nucleophile, solvent, leaving group
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3099

Two sequences are carried out on bromoethane. Sequence I: in aqueous ethanol, then boiling with dilute . Sequence II: in ethanol (covalent, N-bonded reagent), then warming with dilute . Select the correct statements.

  1. AIn sequence I the nitrogen atom of cyanide is the nucleophilic site that bonds to the ethyl carbon.
  2. BSequence I finally gives propanoic acid (as ammonium chloride is also formed).
  3. CSequence II finally gives propanoic acid, since both cyanide reagents form a C-C bond.
  4. DSequence II finally gives ethylammonium chloride and methanoic (formic) acid.

Answer: B, D

Ionic KCN attacks through carbon: , and acid hydrolysis of the nitrile gives with . is covalent, so the lone pair on nitrogen is used and the isocyanide forms. Isocyanides are hydrolysed by dilute acid (not alkali) to a primary amine salt and methanoic acid: . Hence the first two statements are correct.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN1 vs SN2: substrate, nucleophile, solvent, leaving group

More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group