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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

For the given compound, which of the indicated nitrogen atoms has the least tendency to be protonated?

Options

  1. ANitrogen indicated by arrow 'd'
  2. BNitrogen indicated by arrow 'a'
  3. CNitrogen indicated by arrow 'b'
  4. DNitrogen indicated by arrow 'c'

Correct answer

B. Nitrogen indicated by arrow 'a'

Step-by-step solution

In the given compound, the nitrogen atoms indicated by arrows 'b', 'c', and 'd' are pyridine-like nitrogens. They are part of double bonds, and their lone pairs reside in sp^2 hybridized orbitals. These orbitals are orthogonal to the -system of the rings, meaning the lone pairs are localized and readily available to accept a proton. The nitrogen atom indicated by arrow 'a' is a pyrrole-like nitrogen. It is bonded to a hydrogen atom and two carbon atoms via single bonds. Its lone pair resides in an unhybridized p-or

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