Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 31.SE, Problem 18MP
Interpretation Introduction

Interpretation:

Propose the mechanism for the formation of polymeric resin by the reaction of polystyrene with n-(hydroxymethyl) pthalimide and triflouromethanesulphonic acid followed by the reaction with hydrazine.

Concept introduction:

In the Merrifield solid-phase method, peptide synthesis is carried out with the growing amino acid chain covalently bonded to small beads of a polymer resin, rather than in solution.

SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed simultaneously. In first step nucleophilic substitution reaction takes place. Since two reacting species are involved in the slow (rate-determining) step, this leads to the term substitution nucleophilic (bi-molecular) or SN2.

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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE
Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.
Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH
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