Q39 / 125 · BITSAT 2009 · Chemistry

The one which is least basic is

  • A
    $\mathrm{NH}_{3}$
  • B
    $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}$
  • Correct answer
    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

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)

Hence, the correct answer is option: 'C'.

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