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JEE Main levelSingle correct optionDifficulty 2 of 3o1021

Compared with ethoxide, is

  1. Aan equally strong base but a better nucleophile because it is larger
  2. Ba stronger base and a better nucleophile
  3. Ca stronger base but a poorer nucleophile, because of steric hindrance
  4. Da weaker base and a poorer nucleophile

Answer: C

Tert-butanol (pKa about 17) is less acidic than ethanol (pKa about 16), so tert-butoxide is the stronger base. Its three methyl groups shield the oxygen, so it attacks a carbon centre slowly. Basicity is an attack on a small proton and is insensitive to bulk, whereas nucleophilicity is not.
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More questions on Electrophiles, nucleophiles, nucleophilicity and leaving groups