Q.

Although, phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Why ?

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a

Because carboxylate ion has negative charge delocalized over only one O – atom

b

Because carboxylate ion has negative charge delocalized over two – oxygen atoms

c

Phenoxide ion has equivalent structure

d

Phenoxide ion has negative charge localized on an O – atom

answer is B.

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Detailed Solution

Although, phenoxide ion has more number of resonating structure than carboxylate ion, carboxylic acid is a stronger and than phenol. This is because, the negative charge is delocalized over two electronegative O – atoms in carboxylate ion whereas in phenoxide ion, the negative charge is less effectively delocalized over one oxygen atom and less electronegative C – atoms as shown below.

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