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CH,OCH,CI SnCl, CH,CI The chloromethylated polystyrene resin used for Merrifield solid-phase peptide synthesis is prepared by treatment of polystyrene with chloromethylmethyl ether and a Lewis acid catalyst. The reaction involves the following steps: 1. Reaction of the ether with the Lewis acid to form cation 1; 2. Electrophilic aromatic substitution to form resonance stzbilized cation 2: 3. Deprotonation yields aromatic ether 3: 4. Protonation to žorm protonated ether 4; 5. Displacement by chloride ion to form the final product Write out the mechanism on a separate sheet of paper and then draw the structure of the resonance contributors of the resonance stabilized cation 2. • Use Rl groups to indicate the points where the polymer repeats. The R group tool is located in the charges and lone pairs drop-down menu. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu - [F

CH,OCH,CI SnCl, CH,CI The chloromethylated polystyrene resin used for Merrifield solid-phase peptide synthesis is prepared by treatment of polystyrene with chloromethylmethyl ether and a Lewis acid catalyst. The reaction involves the following steps: 1. Reaction of the ether with the Lewis acid to form cation 1; 2. Electrophilic aromatic substitution to form resonance stzbilized cation 2: 3. Deprotonation yields aromatic ether 3: 4. Protonation to žorm protonated ether 4; 5. Displacement by chloride ion to form the final product Write out the mechanism on a separate sheet of paper and then draw the structure of the resonance contributors of the resonance stabilized cation 2. • Use Rl groups to indicate the points where the polymer repeats. The R group tool is located in the charges and lone pairs drop-down menu. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu - [F

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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CH,OCH,CI SnCl, CH,CI The chloromethylated polystyrene resin used for Merrifield solid-phase peptide synthesis is prepared by treatment of polystyrene with chloromethylmethyl ether and a Lewis acid catalyst. The reaction involves the following steps: 1. Reaction of the ether with the Lewis acid to form cation 1; 2. Electrophilic aromatic substitution to form resonance stzbilized cation 2: 3. Deprotonation yields aromatic ether 3: 4. Protonation to žorm protonated ether 4; 5. Displacement by chloride ion to form the final product Write out the mechanism on a separate sheet of paper and then draw the structure of the resonance contributors of the resonance stabilized cation 2. • Use Rl groups to indicate the points where the polymer repeats. The R group tool is located in the charges and lone pairs drop-down menu. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu ChemDoodle"
Transcribed Image Text:CH,OCH,CI SnCl, CH,CI The chloromethylated polystyrene resin used for Merrifield solid-phase peptide synthesis is prepared by treatment of polystyrene with chloromethylmethyl ether and a Lewis acid catalyst. The reaction involves the following steps: 1. Reaction of the ether with the Lewis acid to form cation 1; 2. Electrophilic aromatic substitution to form resonance stzbilized cation 2: 3. Deprotonation yields aromatic ether 3: 4. Protonation to žorm protonated ether 4; 5. Displacement by chloride ion to form the final product Write out the mechanism on a separate sheet of paper and then draw the structure of the resonance contributors of the resonance stabilized cation 2. • Use Rl groups to indicate the points where the polymer repeats. The R group tool is located in the charges and lone pairs drop-down menu. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu ChemDoodle"
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