Which of the following is incorrect?

Options

A. Phenol is much more acidic than alcohol
B. Aqueous hydroxides convert phenol into their salts while aqueous mineral acids convert the salts back into free phenols
C. Like carboxylic acids, most phenols are soluble in aqueous sodium bicarbonate `(NaHCO_(3))`
D. Methyl phenols (cresols) are less acidic than phenol it self while nitrophenols are more acidic

Answer

C

Explanation

Most phenols are weaker acids than carbonic acid, and hence, unlike carboxylic acids, do not dissolve in aqueous bicarbonate solution. Thus, aqueous `NaHCO_(3)` provides a method for distinguishing and separating most phenols from carboxylic acids. Phenols are conveniently liverated form their salts by the aciton of carbonic acid:
`CO_(2)+H_(2)O hArr H_(2)CO_(3)`

Since phenol is a weaker acid than carbonic acid, it can be separated from carboxylic acids by making the soolution alkaline with sodium salt and so many be extracted with ether. The carboxylic acid salts are not decomposed by carbon dioxide.
(1) The negative charge on the alkoxide anion, `RO^(-)` , is completely localized while the negative charge on the phenoxide anion, `PhO^(-)`, is delocalized by extended `pi` bonding to the orhto and para ring position as indicarted By `delta-`in the resonance hybrid.

Therefore `PhO^(-)` is a weaker base than `RO^(-)` and hence `PhOH(ArOH)` is a stronger acid than `ROH`
(2)
(4) Electron donating `(ED)` substituents such as alkyl groups concentrate negative charges , malking `ArO^(-)` a stronger base and the phenol a weaker acid.

Electron attracting `(EA)` substituents disperse negative charges, making `ArO^(-)` a weaker base and the phenol a stronger acid.