JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g2108
An ether solution contains aniline, benzoic acid (pKa 4.20), phenol (pKa 10.0) and toluene. Using pKaH of anilinium 4.6 and pKa of HX2COX3 6.4, which statements about extraction with aqueous solutions are correct?
ADilute HCl extracts aniline into the aqueous layer as anilinium chloride
BAqueous NaHCOX3 extracts benzoic acid but not phenol
CAqueous NaOH (after the earlier extractions) can extract phenol
DAqueous NaHCOX3 extracts phenol as well as benzoic acid
Answer: A, B, C
Aniline is basic enough to be protonated by dilute HCl. Bicarbonate (conjugate acid pKa 6.4) deprotonates benzoic acid (4.20) but not phenol (10.0). Hydroxide (15.7) deprotonates phenol. D is false, and toluene remains in the ether.