You carefully purified phenanthrene from a very long, complicated ...

[arivle123]

You carefully purified phenanthrene from a very long, complicated procedure. It took days. It
  is very important for you to hand the purified phenanthrene in to your instructor in one hour
  to get a good grade. Oops You accidentally put the phenanthrene into a vial that you thought
  was clean but instead had a lot of NaCl clinging to the sides. What can you do to quickly
  purify the phenanthrene again?

Question 2

What is wrong with the following procedure?
  The reaction mixture, consisting of NaBr and an ethanol solution of the product, is diluted
  with an equal volume of water, then extracted once with an equal volume of diethyl ether. The
  lower aqueous layer is discarded.

[LegendaryAnswers]

Answer to Question 1

Add a small amount of water to dissolve the NaCl and then extract into an organic solvent,
such as hexanes or methylene chloride.

Answer to Question 2

Ethanol is miscible with both water and diethyl ether. Therefore, a substantial amount of ethanol, diethyl ether, and product would be present in the discarded water layer. Before such an
extraction is carried out, most of the ethanol should be evaporated from the original mixture.