Question

Question 8 Status: Incomplete answer Points possible: 1.00 When separating benzoic acid, naphthalene, and aniline, identify the solution used for each described purpose. Extract aniline into the aqueous layer Choose... Extract reconstituted benzoic acid out of the aqueous layer Choose... Choose... Choose... Reconstitute benzoic acid from aqueous layer Reconstitute aniline from aqueous layer Extract benzoic acid into the aqueous layer Extract reconstituted aniline out of the aqueous layer Please answer all parts of the question. Choose... Choose...

Answer 1

Extract aniline in aq layer : Add aq HCl

Extract reconstituted benzoic acid in aq layer : Add ether (diethyl ether)

Reconstitute benzoic acid from aq layer : Add HCl

Reconstitute aniline from aq layer : Add NaOH

Extract benzoic acid into aq layer : Add aq NaOH

Extract reconstituted aniline out of aq layer : Add ether (diethyl ether)

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Mixture of benzoic acid (BA)(organic acid), aniline (organic base), and naphthalene (neutral organic molecule), all are soluble in the solvent diethyl ether.

To separate aniline (organic base) from ether solution, do an acidic extraction of the organic base. To the ether solution containing naphthalene, BA and aniline, aq HCl is added. This acid reacts with the amine to form an ammonium salt. The ammonium salt is water-soluble and goes into the aqueous layer.

To isolate aniline(reconstitution), the acidic solution can be basified (add aq NaOH) followed by the addition of ether to extract the neutral aniline into ether.

To separate BA (organic acid) from ether solution, do an basic extraction of the organic acid. To the ether solution containing naphthalene, BA and aniline, aq NaOH is added. This base reacts with the BA to form an sodium benzoate salt. The sodium benzoate salt is water-soluble and goes into the aqueous layer.

To isolate BA(reconstitution), the basic solution can be acidified (add aq HCl) followed by the addition of ether to extract the neutral BA into ether.