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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 63AP: As far back as the 16th century, South American Incas chewed the leaves of the coca bush,...

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