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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3107

1,4-Dibromobutane ( mol) is heated with mol of potassium phthalimide in DMF and the product is then boiled with hydrazine hydrate. The final organic product is

  1. Abutane-1,4-diamine
  2. B4-bromobutan-1-amine
  3. Cpyrrolidine
  4. Dbutan-1-amine

Answer: A

The phthalimide anion is a good nucleophile that is not strongly basic, and DMF increases its reactivity. With 2 mol of reagent, both primary C-Br bonds are displaced by SN2 to give the bis(phthalimide). Hydrazine then removes both phthaloyl groups and gives the diamine . The phthalimide nitrogen cannot be alkylated twice, so no secondary amine is formed.
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More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group