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Question

A mixture of toluene, benzoic acid, aniline and phenol was dissolved in diethyl ether and extracted with 5%NaHCO3 solution. This extract was acidified until a white crystalline compound appeared. What is the identity of this compound?

A
Toluene
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B
Benzoic acid
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C
Aniline
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D
Phenol
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Solution

The correct option is C Benzoic acid
Toluene is a neutral compound and aniline is a base. They do not react with sodium bicarbonate which acts as a weak base.
Phenol is a very weak acid and does not react with sodium bicarbonate.
Benzoic acid reacts with sodium bicarbonate to form water soluble sodium benzoate. On neutralization, sodium benzoate regenerates benzoic acid.
C6H5COOHNaHCO3−−−−−C6H5COONaH+C6H5COOH

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