Here is a flowchart for the separation of a mixture of a primary aliphatic amine (RNH, pK, 10.8), a carboxylic acid (RCOOH, pK, 5), and a phenol (ArOH, pK, 10). Assume that each is insoluble in water but soluble in diethyl ether. The mixture is separated into fractions A, B, and C. Which fraction contains the amine, which contains the carboxylic acid, and which contains the phenol? A mixture of three compounds RNH, Amine Carboxylic acid Phenol RCOOH AFOH Dissolve in diethyl ether Mix with HCI, H,0 Ether layer Aqueous layer Add NafICO, H,O Add diedhyl echer. NAOH, H,0 Aqueous layer Aqueous layer Ether layer Ether layer Add dieuhyl ether. HCI, H,0 Evaporate ether Evaporate ether B Aqueous layer Ether layer Evaporate ether

Macroscale and Microscale Organic Experiments
7th Edition
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Kenneth L. Williamson, Katherine M. Masters
Chapter7: Extraction
Section: Chapter Questions
Problem 1Q
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In what way(s) might the results of the separation and purification procedure
outlined  be different if the following conditions exist?

Q. Aqueous NaOH is used in place of aqueous NaHCO3.

Here is a flowchart for the separation of a mixture of a primary aliphatic amine
(RNH, pK, 10.8), a carboxylic acid (RCOOH, pK, 5), and a phenol (ArOH,
pK, 10). Assume that each is insoluble in water but soluble in diethyl ether.
The mixture is separated into fractions A, B, and C. Which fraction contains the
amine, which contains the carboxylic acid, and which contains the phenol?
A mixture of three compounds
RNH,
Amine Carboxylic acid Phenol
RCOOH
AFOH
Dissolve in diethyl ether
Mix with HCI, H,0
Ether layer
Aqueous layer
Add NafICO, H,O
Add diedhyl echer. NAOH, H,0
Aqueous layer
Aqueous layer
Ether layer
Ether layer
Add dieuhyl ether. HCI, H,0
Evaporate ether
Evaporate ether
B
Aqueous layer
Ether layer
Evaporate ether
Transcribed Image Text:Here is a flowchart for the separation of a mixture of a primary aliphatic amine (RNH, pK, 10.8), a carboxylic acid (RCOOH, pK, 5), and a phenol (ArOH, pK, 10). Assume that each is insoluble in water but soluble in diethyl ether. The mixture is separated into fractions A, B, and C. Which fraction contains the amine, which contains the carboxylic acid, and which contains the phenol? A mixture of three compounds RNH, Amine Carboxylic acid Phenol RCOOH AFOH Dissolve in diethyl ether Mix with HCI, H,0 Ether layer Aqueous layer Add NafICO, H,O Add diedhyl echer. NAOH, H,0 Aqueous layer Aqueous layer Ether layer Ether layer Add dieuhyl ether. HCI, H,0 Evaporate ether Evaporate ether B Aqueous layer Ether layer Evaporate ether
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