20. A mixture of toluene, benzoic acid, aniline and phenol was dissolved in diet

Question

20. A mixture of toluene, benzoic acid, aniline and phenol was dissolved in diethyl ether and extracted with 0.1 M NaHCO3 solution. This aqueous extract was acidified until a white crystalline compound appeared. What is the identity of the crystalline compound? (Hint: see pKa table below) CH3 NH2 toluene benzoic acid aniline phenol a. toluene b. benzoic acid c. aniline d. phenol pKa Values Formula C&HsCH3; CsHSNH2 pKa 41 Acid Toluene Aniline Phenol Carbonic Acid Protonated Aniline Benzoic Acid C&HsOH27; 9.95 6.36 5.2 4.19 H2CO3 C&H;,COOH

Explanation / Answer

20. B

Benzoic acid has the smallest pKa value whichmeans it is the most acidic. Weak base like NaHCO3 can dissolve it in aqueous solution. And when it is acidified again white crystalline compound is obtained.

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