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Fundamentals of Organic ChemistryChemistryAmines

Identify the correct decreasing order of nucleophilicity for the following amines: (i) (ii) (iii)

Options

  1. A(i) > (ii) > (iii)
  2. B(ii) > (iii) > (i)
  3. C(iii) > (i) > (ii)
  4. D(i) > (iii) > (ii)

Correct answer

A. (i) > (ii) > (iii)

Step-by-step solution

Nucleophilicity of amines depends on the availability of the lone pair on the nitrogen atom for attack on an electrophile. Steric hindrance plays a major role in determining nucleophilicity; greater steric crowding around the nitrogen atom significantly decreases its nucleophilicity. In compound (i) (quinuclidine), the alkyl groups are constrained in a rigid bicyclic ring system. This structural feature "ties back" the alkyl chains, exposing the lone pair on the nitrogen atom. Due to minimal steric hindrance, it is

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