The relative acidity between carboxylic acids has been used as a means for determining the electron-withdrawing...

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Chemistry

The relative acidity between carboxylic acids has been used as ameans for determining the electron-withdrawing or electron-donatingabilities of substituents.
a) The pKa of phenyl acetic acid is 4.31, making it a strongeracid than acetic acid. Is the Ph group electron-donating orelectron-withdrawing in this case?
b) The Ph group is a mild o,p-director in EAS reactions. Is thePh group electron-donating or electron-withdrawing? If the answercontradicts your answer from part a, provide an explanation.
c) 4-Methoxybenzoic acid is a weaker acid than benzoic acid, yetmethoxyacetic acid is a stronger acid than acetic acid. Rationalizethese seemingly contradictory results.
d) Methyl groups are usually considered electron-donatinggroups. Propanoic acid is a weaker acid than acetic acid. Is thatresult in agreement?

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4.4 Ratings (601 Votes)

aThe pKa of phenyl acetic acid is 431 making it a stronger acid than acetic acid Is the Ph group electrondonating or electronwithdrawing in this case Ans Phenyl is electron withdrawing group in this case which makes phenyl acetic acid more stronger b The Ph group is a mild opdirector in EAS reactions Is the Ph group electrondonating or See Answer

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