following this chart answer the following question: if you mistakenly extracted

Question

following this chart answer the following question:

if you mistakenly extracted the ether solution first with NaOH solution and then with NaHCO3 solution, no crystals would be produced upon acidification of the NaHCO3 layer. briefly explain!! please help!!!

tert-butyl methyl ether CsH,NHCOCH3 (acetanilide) P-CH3-CsH4-COOH (p-toluic acid) p-C4H9-c6H40h(p-tert-butylphenol) mix -NaHCO3 solution 2 ether layer aqueous layer (extraction) C6HNHCOCH3 HCO3Na HCI solution 3 -NaOH solution ether aqueousfiltrate residue (extraction) (filtration) discard CeH,NHCOCH 5 _-HCl solution 6Na2SO4 residue (anhydrous) filtrate (fitration) decantate residue discard (decantation) CoHsNHCOCH3 discard vapor residue (evaporate discard CGHsNHCOCH3 Figure 8 Flowchart for separations using microscale techniques

Explanation / Answer

p-toluic acid is strong acid and p-tert butyl phenol is weak acid.

NaHCO3 is weak base. It reacts with p-toluic acid only. It does not react with p-tert butyl phenol.

NaOH is strong base. It reacts with p-toluic acid and p-tert butyl phenol.

If you mistakenly extracted the ether solution first with NaOH solution, then aqueous layer will contain sodium salt of p-toluic acid and sodium salt of p-tert butyl phenol. Ether layer will contain acetanilide.

Hence, when you extract ether layer (containing only acetanilide) with NaHCO3 solution, no crystals would be produced upon acidification of the NaHCO3 layer as p-tert butyl phenol is not present in this layer.

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