MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition / Solvent effects on reactions
JEE Advanced levelSingle correct optionDifficulty 3 of 3o1046

Relative rate constants (hypothetical, all scaled to in methanol = 1.0) for at 25 C are: in methanol, 1.0, 20, 90; in DMF, 4000, 1400, 500. Which conclusion follows from these data?

  1. ADMF decreases the rate for all three ions, with affected most
  2. BChanging to DMF reverses the order, and is accelerated most (about 90-fold)
  3. CChanging to DMF leaves the order unchanged and accelerates most (about 500-fold)
  4. DChanging from methanol to DMF reverses the order of nucleophilicity, and is accelerated most (about 4000-fold)

Answer: D

Acceleration (DMF/methanol): = 4000/1.0 = 4000, = 1400/20 = 70, = 500/90 = 5.56. The smallest, most strongly hydrogen-bonded ion gains most. The order is in methanol (90 > 20 > 1) but in DMF (4000 > 1400 > 500).
Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Solvent effects on reactions

More questions on Solvent effects on reactions