Question:
Give reasons of the following:
(i) Aniline does not exhibit Friedel–Crafts reaction.
(ii) Ethyl amine is soluble in water while aniline is not.
Give reasons of the following:
(i) Aniline does not exhibit Friedel–Crafts reaction.
(ii) Ethyl amine is soluble in water while aniline is not.
(ii) Ethyl amine is soluble in water while aniline is not.
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Remember: Solubility in water depends on hydrogen bonding capacity and molecular size.
Updated On: Oct 7, 2025
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Solution and Explanation
(i) Friedel–Crafts reaction.
Aniline reacts with Lewis acid catalysts (like AlCl\(_3\)) forming insoluble complexes. This deactivates the benzene ring, preventing Friedel–Crafts alkylatiocylation.
(ii) Solubility difference.
Ethyl amine: Small size, strong H-bonding with water → soluble.
Aniline: Bulkier phenyl group decreases polarity and reduces hydrogen bonding with water → very low solubility.
Step 3: Conclusion.
(i) Aniline does not undergo Friedel–Crafts due to catalyst complexation.
(ii) Ethyl amine soluble; Aniline not soluble.
Aniline reacts with Lewis acid catalysts (like AlCl\(_3\)) forming insoluble complexes. This deactivates the benzene ring, preventing Friedel–Crafts alkylatiocylation.
(ii) Solubility difference.
Ethyl amine: Small size, strong H-bonding with water → soluble.
Aniline: Bulkier phenyl group decreases polarity and reduces hydrogen bonding with water → very low solubility.
Step 3: Conclusion.
(i) Aniline does not undergo Friedel–Crafts due to catalyst complexation.
(ii) Ethyl amine soluble; Aniline not soluble.
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