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3. Using information available in the Merck Index (access on Ryerson's library website) to answer
the following questions. (1 mark)
a. What is the partition coefficient for 3-nitroaniline between diethyl ether and water (at 20 C and pH > 8)
b. What is the partition coefficient for benzoic acid between diethyl ether and water (at 20 C and pH < 2.8)
4. Suppose that benzophenone (a neutral compound) were added to the benzoic acid and 3-
nitroaniline that you extracted. Outline the steps that you would take to isolate the benzophenone
from the mixture? (1 mark)
5. Suppose that you have a reaction mixture which consists of 13.2 g of KBr and 11.0 g of an
interesting organic compound dissolved in 100 mL of water. You would like to have the pure
organic compound, separate from water and salt, so you decide to carry out an extraction. You
add 100 mL of dichloromethane and vigourously shake in a separatory funnel.
a) After settling, both layers are clear colourless liquids. How do you know which layer is the organic
layer? (1 mark)
b) After separating the organic from the aqueous layer, and evaporating the organic solvent you find that
you have recovered 7.0 g of the interesting organic compound. What is this compound's partition
coefficient with dichloromethane? (1 mark)
c) If you then add the remaining aqueous solution back into the separatory funnel, along with 100 mL of
fresh dichloromethane, and perform another extraction, how much more of the interesting compound
would you expect to recover? (Hint: This requires you to consider how much of the interesting
compound remains in the aqueous phase after the first extraction.) (1 mark)
d) Suppose that instead of two successive extractions with 100 mL of dichloromethane each time, you
had used all 200 mL of dichloromethane in a single extraction. How much of the interesting compound
would you expect to have recovered? (1 mark)

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