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Question

Which of the following is least basic?


A

(CH3CO)2NH

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B

(CH3CO)NHC2H5

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C

(C2H5)3N

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D

(C2H5)2NH

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Solution

The correct option is A

(CH3CO)2NH


The explanation for the correct option:

(a) (CH3CO)2NH

  1. Basicity of amines is the tendency to donate the lone pair of electrons of N(nitrogen) in a chemical reaction, more easily it can donate more will be the basicity.
  2. The presence of electron-withdrawing and conjugation of lone pair decreases the basicity.
  3. The presence of an electron-donating group increases the basicity.
  4. Here, the lone pair of N is engaged in conjugation with two carbonyl groups and the lone pair is not available for donation conjugation.
  5. So, it will be the least basic.

The explanation for incorrect option:

(b) (CH3CO)NHC2H5

  1. Here, there is carbonyl group which will be engage the lone pair in conjugation.
  2. But, there is alkyl group as well, which shows +I effect.
  3. So, it will be more basic than (a)

(c) (C2H5)3N

  1. It is a tertiary amine with three alkyl group which will show +I effect and increase the basicity.
  2. It will be most basic.

(d) (C2H5)2NH

  1. It is a secondary amine with two alkyl which will show +I effect and increase the basicity.
  2. It will be more basic but less than (c)

Therefore, Option (a) is correct option, (CH3CO)2NH is least basic.


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