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Assignment 2 Answers - CHM 2120 Assignment#2 ANSWERS In...

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CHM 2120 – Assignment #2 – ANSWERS In this assignment: - Separation of organic compounds using acid/base techniques - Acids/Bases - S N 2, S N 1, E2, E1 1. How would you separate the following mixtures of compounds? a. Octan-1-ol and octan-1-amine Dissolve both in EtOAc. Add a 10% HCl solution in H 2 O, which protonates the amine. Now the octan-1-ol is in the EtOAc, and the protonated (charged) amine is in the aqueous layer. Separate the organic and aqueous layers. Evaporate the organic layer to obtain pure octan-1-ol. Deprotonate the amine to make it neutral by adding a 10% NaOH solution in H 2 O. Extract the aqueous layer with EtOAc. The neutral amine dissolves best in the organic layer. Separate the layers and evaporate the EtOAc to obtain pure octan-1-amine. OH NH 2 OH In EtOAc NH 3 In aqueous layer NH 2 in EtOAc Salts (ex: NaCl) in aqueous layer Add HCl (aq) And EtOAc Add NaOH (aq) and EtOAc Pure OH Evaporate the EtOAc Pure NH 2 Evaporate the EtOAc
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Assignment 2 - Answers 2 b. Cyclohexanecarboxylic acid from nitrobenzene Dissolve both in EtOAc. Add a 10% NaOH solution in H 2 O, which deprotonates the carboxylic acid. Now we have nitrobenzene in the organic layer, and the deprotonated (charged) cyclohexanecarboxylic acid (a carboxylate) in the aqueous layer. Separate the organic and aqueous layers. Evaporate the organic layer to obtain pure nitrobenzene. Protonate the carboxylate by adding a 10% HCl solution in H 2 O. Extract the aqueous layer with EtOAc. The neutral acid dissolves best in the organic layer. Separate the layers and evaporate the EtOAc to obtain pure cyclohexanecarboxylic acid. c. OH O NO 2 NO 2 In EtOAc O O In aqueous layer OH O in EtOAc Salts (ex: NaCl) in aqueous layer Add NaOH (aq) And EtOAc Add HCl (aq) and EtOAc Pure NO 2 Evaporate the EtOAc Pure OH O Evaporate the EtOAc
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Assignment 2 - Answers 3 CO 2 H Ibuprofen (advil) and H N O Same procedure as in part B.
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