Assignment_2_SN2_elimination_Answers

Assignment_2_SN2_elimination_Answers - CHM 2120 Assignment...

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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 3 In aqueous layer 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 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 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 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. 2. Which of the following is the strongest, and which is the weakest base? a) CH 3 CH 2 O - b) CH 3 CH 2 OH; c) CH 3 CH 2 S - d) CH 3 CH 2 CO 2 - e) CH 3 CH 2 NH 2 Strongest base: a; Weakest base: b 3. Which of the following is the strongest, and which is the weakest nucleophile?
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This note was uploaded on 01/25/2011 for the course CHM 2120 taught by Professor Dr.flynn during the Spring '10 term at University of Ottawa.

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Assignment_2_SN2_elimination_Answers - CHM 2120 Assignment...

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