Consider the oxidation reaction shown below. A TLC of the starting material (phenylacetaldehyde) is shown to the left using 50% Ethyl acetate/50% hexanes as the solvent system. Answer the following questions about this reaction: 50/50 EtOAc/hexanes Oxidation OH phenylacetaldehyde phenethyl carboxylic acid a) Draw a TLC plate of the reaction using 50% EtOAc/50% hexanes as your solvent system assuming approximately 50% conversion of phenylacetaldehyde to phenethyl carboxylic acid (lane 1 = starting material, lane 2 = reaction mixture) 12 50/50 EtOAc/hexanes b) Draw a TLC of the reaction using 50% EtOAc/50% hexanes as your solvent system assuming 90% conversion of phenylacetaldehyde to phenethyl carboxylic acid (lane 1 = starting material, lane 2 = reaction mixture) 1 2 50/50 EtOAc/hexanes c) Draw a TLC of the reaction mixture using 80/20 Ethyl acetate/hexanes as your solvent system assuming 90% conversion of phenylacetaldehyde to phenethyl carboxylic acid (lane 1 = starting material, lane 2 = reaction mixture) 1 2 80/20 EtOAc/hexanes d) The reaction was conducted in Ethyl acetate (reaction solvent). No matter how hard you tried, the reaction did not progress more than 90% to completion. Write a procedure how you would purify the reaction and isolate the pure solid phenethyl carboxylic acid using acid/base extraction

Consider the oxidation reaction shown below. A TLC of the starting material (phenylacetaldehyde) is shown to the left using 50% Ethyl acetate/50% hexanes as the solvent system. Answer the following questions about this reaction: 50/50 EtOAc/hexanes Oxidation OH phenylacetaldehyde phenethyl carboxylic acid a) Draw a TLC plate of the reaction using 50% EtOAc/50% hexanes as your solvent system assuming approximately 50% conversion of phenylacetaldehyde to phenethyl carboxylic acid (lane 1 = starting material, lane 2 = reaction mixture) 12 50/50 EtOAc/hexanes b) Draw a TLC of the reaction using 50% EtOAc/50% hexanes as your solvent system assuming 90% conversion of phenylacetaldehyde to phenethyl carboxylic acid (lane 1 = starting material, lane 2 = reaction mixture) 1 2 50/50 EtOAc/hexanes c) Draw a TLC of the reaction mixture using 80/20 Ethyl acetate/hexanes as your solvent system assuming 90% conversion of phenylacetaldehyde to phenethyl carboxylic acid (lane 1 = starting material, lane 2 = reaction mixture) 1 2 80/20 EtOAc/hexanes d) The reaction was conducted in Ethyl acetate (reaction solvent). No matter how hard you tried, the reaction did not progress more than 90% to completion. Write a procedure how you would purify the reaction and isolate the pure solid phenethyl carboxylic acid using acid/base extraction

EBK A SMALL SCALE APPROACH TO ORGANIC L

4th Edition

ISBN:9781305446021

Author:Lampman

Publisher:Lampman

Chapter5: Chromatography

Section: Chapter Questions

Problem 1Q

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