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JEE Main levelSingle correct optionDifficulty 2 of 3o1069

Imine formation from a ketone and a primary amine is fastest at about pH 4-5 and slower both in strongly acidic and in basic solution. Which statement explains this?

  1. AAt low pH the carbonyl oxygen cannot be protonated at all; at high pH the amine is protonated
  2. BAt low pH the imine is too stable to form; at high pH the ketone is oxidised
  3. CAt low pH hydroxide attacks the carbonyl; at high pH the amine undergoes elimination
  4. DAt low pH the amine is largely protonated and not nucleophilic; at high pH there is too little acid to protonate the carbinolamine OH so that water can leave

Answer: D

The two steps of imine formation need opposite conditions. Addition needs free amine, which is lost by protonation in strong acid. Loss of water from the carbinolamine needs acid catalysis, which is lacking in base. The rate therefore peaks at weakly acidic pH.
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