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Question: Answered & Verified by Expert
The one which is least basic is
ChemistryGeneral Organic ChemistryBITSATBITSAT 2009
Options:
  • A $\mathrm{NH}_{3}$
  • B $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}$
  • C $\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{~N}$
  • D $\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \mathrm{NH}$
Solution:
2828 Upvotes Verified Answer
The correct answer is: $\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{~N}$
More the electron density on $\mathrm{N}$, higher will be the basicity. Density on $\mathrm{N}$ is influenced by the (i) nature of the group (+I or -I) present in alkyl group or benzene nucleus and (ii) resonance (delocalisation of the electron present on $\mathrm{N}$ ). In $\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{~N}$ :
electron pair is delocalised to the maximum extent due to three benzene rings and hence least available for protonation, thus it will be least basic)

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