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Chapter 25: PROBLEM 25.21 (page 1019)

Question: Rank the following compounds in order of increasing basicity

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01

Basicity of arylamines and alkylamines

Arylamines (aniline) having a ring accept electrons pairs from the amine group. Therefore, aniline is less basic than alkylamines.

Alkylamines have an alkyl group that donates electrons and increases their basicity.

02

Amide

Amide also contains nitrogen which is bonded with the carbonyl group. The lone pair of electrons in the amide delocalize to the carbonyl group. Therefore, amide is less basic than aniline.

03

Explanation

The increasing order of basicity is as shown.

Increasing basicity order

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Most popular questions from this chapter

Tertiary ( 3°) aromatic amines react with NaNO2 and HCl to afford products of electrophilic aromatic substitution. Draw a stepwise mechanism for this nitrosation reaction and explain why it occurs only on benzene rings with strong ortho, para activating groups.

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