4. a) Place the following compounds in order of increasing acidity of their most acidic proton. b) For two of the carboxylic acids, do an ARIO analysis to explain their relative acidities. 4-nitrobenzoic acid, trichloroacetic acid, hydrochloric acid, acetic acid, phenol, 4-methoxyphenol, ethanol, water, ammonia, propyne, propene, cyclopentadiene and hydrogen sulfide.

4. a) Place the following compounds in order of increasing acidity of their most acidic proton. b) For two of the carboxylic acids, do an ARIO analysis to explain their relative acidities. 4-nitrobenzoic acid, trichloroacetic acid, hydrochloric acid, acetic acid, phenol, 4-methoxyphenol, ethanol, water, ammonia, propyne, propene, cyclopentadiene and hydrogen sulfide.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section21.4: Phenols

Problem 21.6P: Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.

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