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JIPMER 2012
Exam
JIPMER
Year
2012
Subject
Chemistry
Chapter
Amines

JIPMER 2012 · Chemistry · Amines

Which of the following is most basic in nature?

Which of the following is most basic in nature?

Options

  1. ANH3\mathrm{NH}_3
  2. BCH3NH2\mathrm{CH}_3 \mathrm{NH}_2
  3. C(CH3)2NH\left(\mathrm{CH}_3\right)_2 \mathrm{NH}
  4. DC6H5 N(CH3)2\mathrm{C}_6 \mathrm{H}_5 \mathrm{~N}\left(\mathrm{CH}_3\right)_2

Correct answer

C. (CH3)2NH\left(\mathrm{CH}_3\right)_2 \mathrm{NH}

Step-by-step solution

Basicity of amines depends upon the availability of lone pair of nitrogen for donation. Electron releasing group like −CH3-\mathrm{CH}_3 increases the basicity of amines by increasing electron density over nitrogen, which facilitate the donation of lone pair of electrons. Electron withdrawing groups like -Ph group withdraws electrons and thus, make amines less basic by decreasing electron density over nitrogen. Hence, the order of basic nature of the given amines is (CH3)2NH>C6H5 N(CH3)2>CH3NH2>NH3\left(\mathrm{CH}_3\right)_2 \mathrm{NH}\gt\mathrm{C}_6 \mathrm{H}_5 \mathrm{~N}\left(\mathrm{CH}_3\right)_2\gt\mathrm{CH}_3 \mathrm{NH}_2\gt\mathrm{NH}_3 Thus, (CH3)2NH\left(\mathrm{CH}_3\right)_2 \mathrm{NH} is most basic.
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