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)

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. hope this helps

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