2) You have toseparate 4-toluic acid (a strong acid, pKa 4.36 – look upstructure

Question

2) You have toseparate 4-toluic acid (a strong acid, pKa 4.36 – look upstructure) from 4-bromoaniline (a base – look up structure).Assume the two substances don’t react with each other. Themixture of 4-toluic acid and 4-bromoaniline is dissolved in ether.You MAY need the following information: The pKa of HCl is –7;pKa of carbonic acid is 6.52 and the pKa of water is 15.

a) Why would using either sodium bicarbonate or sodium hydroxide beable to extract 4-toluic acid into the aqueous layer? (Give reasonsfor both)

b) What would the name of the species in the aqueous layer be whenthe mixture mentioned above is extracted with either sodiumhydroxide or sodium bicarbonate?

Explanation / Answer

since sodium hydroxide is a strong base it will react easily with4-toluic acid to give the neutralization product. In case of sodiumbicarbonate, it is a weak base and it reacts with strong acid4-toluic acid and forms sodium salt of carboxylic acid. sodium para toluate (sodium salt of 4-toluic acid) hope this helps

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