Question

Rank the following substituted anilines from most basic to least basic:

Short answer

The order followed as:

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Step-by-step solution

Basicity of aniline

The compound has high electron density and has the capability to donate the free electron pairs are highly basic in nature and have a high pka value like in aniline N has lone pair freely to donate hence basic in nature.

Order of basicity

Methoxy aniline is more basic in nature due to the presence of oxygen having lone pairs which help in delocalization and that makes it more basic in nature.

Then, methyl aniline due to the presence of an alkyl and electron-donating group becomes basic in nature.

Then, in Bromo aniline due to presence of bromine which is an electron-withdrawing group makes it less basic in nature.

The least basic is acetanilide due to the presence of carbonyl which is highly electron-withdrawing in nature and withdraws all the electron density towards carbonyl oxygen making it less basic in nature.

The order followed as:

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Order of Basicity of aniline