EXTRACTION- SEPARATION OF A MIXTURE

Purpose: To separate a mixture of benzoic acid (strong acid), 2-naphthol (weak acid) and
p-dimethoxybenzene (neutral substance) by extraction.
Procedure: Accurately weigh approximately 3 g of the three-component mixture from your
instructor and dissolve it in 25 mL ether. Be sure to dissolve the entire sample since it is not
homogeneous. Pour the solution into a 125 ml separatory funnel. To extract the benzoic acid
from the mixture, add 10 mL f 10% aqueous sodium bicarbonate and shake thoroughly. Draw
off the lower (aqueous) layer into 125 mL Erlenmeyer flask and repeat the extraction with a
second portion of sodium bicarbonate. Finally, extract with 10 ml of water, to remove excess
sodium bicarbonate, which may be dissolved in the ether layer. Combine the three extracts
and then set this mixture aside.
To separate the 2-naphthol from the mixture, extract the ether solution twice with 10 mL of
10% NaOH and once with water. Combine the alkaline layers and set aside.
Pour out the remaining ether solution (which should contain only the p-dimethoxybenzene)
through the neck of the separatory funnel into a small Erlenmeyer flask, add a few granules
of anhydrous CaCl2 and shake the mixture occasionally for 15 minutes. Decant the ether into
a small weighed beaker and place it in the hood to allow the ether to evaporate. Weigh the
residue and determine its melting point.
Neutralize the combined sodium bicarbonate extracts by adding conc. HCl until addition of a
drop of HCl causes no additional precipitation. Cool and isolate the product by vacuum
filtration using a Hirsch funnel. Recrystallize from hot water. After drying weigh and
determine the melting point.
Neutralize the combined NaOH extracts by adding cone. HCl until addition of a drop of HCI
causes no additional precipitation. The solution may be kept cool with ice during
neutralization. Recover the precipitated 2-naphthol by vacuum filtration, and recrystallize
from hot water. Dry, and determine the melting point. Turn in the benzoic acid and the
2-naphthol to your instructor

Benzoic Acid

2-Naphthol

p-dimethoxybenzene

Name__________________________
_________
EXTRACTION: SEPARATION OF ACIDIC AND NEUTRAL SUBSTANCES
Sample # _______________
Compound

Weight Recovered

Melting Point

% in Unknown

Benzoic Acid
2-Naphthol
p-Dichlorobenzene
Questions:
1. What are the advantages and disadvantages of using ether as an extraction solvent?

2.

In extracting an organic compound from an aqueous solution, what practical

advantage ensues if the organic solvent used is more dense than water?

3.

Why must the stopper be removed from a separatory funnel before liquid can be.
withdrawn from it?

4.

Outline a method for separating the following mixture into its pure components. Use
back of sheet if necessary.

p-toluidine
(basic)
(neutral)

2-naphthol

p-dimethoxybenzene

Soalnya sama kaya no 3 tapi Cuma sampai Baja

Find the concentration of iodine remaining in the
aqueous layer after extraction?
The distribution coefficient for iodine between an organic solvent and water is 85.
Find the concentration of iodine remaining in the aqueous layer after extraction of
50.0 ml of 1.00 x 10-3 M iodine with the following quantities of the organic solvent:
a. Single extraction with 50.0 ml of the organic solvent.
b. Two successive extraction with 25.0-ml portions of the organic solvent.
c. Five successive extration with 10.0-ml portions of the organic solvent. What is
the percentage of iodine extracted?
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Answers

Best Answer: The formula to use is:

[I2]aq = [Vaq/(VorgK+Vaq)]^i X [I2]initial
a. [I2]aq = [50/(50(85) +50)]^1 X 1X10^-3 = 1.16X10^-5 M
b. [I2]aq = [50/(25(85)+50)]^2 X 1.00X10^-3 = 5.28X10^-7 M
Just repeat the calculation for c.