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JEE Main levelSingle correct optionDifficulty 2 of 3o3082

Sodium phenoxide reacts with bromoethane in DMF at . The major product is

  1. A (ethoxybenzene)
  2. B2-ethylphenol
  3. C4-ethylphenol
  4. D and ethene only

Answer: A

Phenoxide is an ambident nucleophile that can react at oxygen or at the ring carbons ortho/para to oxygen. In a polar aprotic solvent such as DMF, where the oxygen is not hydrogen bonded, the highly charged oxygen is the more nucleophilic site and the kinetic product is the aryl alkyl ether, ethoxybenzene (Williamson synthesis).
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