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Which of the following amines is the strongest base?Select answer from the options below3-chloroanilineaniline4-aminoaniline4-methylaniline

Question

Which of the following amines is the strongest base?Select answer from the options below3-chloroanilineaniline4-aminoaniline4-methylaniline

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Solution

The basicity of amines is determined by the availability of the lone pair of electrons on the nitrogen atom for donation. Electron-donating groups increase basicity by increasing the electron density on the nitrogen, while electron-withdrawing groups decrease basicity by decreasing the electron density on the nitrogen.

  1. 3-chloroaniline: The chlorine atom is an electron-withdrawing group. It will decrease the electron density on the nitrogen, making it less basic.

  2. Aniline: Aniline is a weak base due to the delocalization of the lone pair of electrons on the nitrogen into the benzene ring.

  3. 4-aminoaniline: The amino group at the 4th position is an electron-donating group. It will increase the electron density on the nitrogen, making it more basic.

  4. 4-methylaniline: The methyl group at the 4th position is also an electron-donating group. It will increase the electron density on the nitrogen, making it more basic.

Comparing 4-aminoaniline and 4-methylaniline, the amino group is a stronger electron-donating group than the methyl group. Therefore, 4-aminoaniline is the strongest base among the given options.

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