Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 28.6, Problem
Interpretation Introduction

(a)

Interpretation: The structure of prepolymer A formed from 1,4-dihydroxybenzene and excess epichlorohydrin is to be stated.

Concept introduction: Epoxides are strained three-membered rings. They undergo anionic polymerization to afford the ring opening, by following the SN2 pathway. The ring opening in an unsymmetrical epoxide takes place at the less substituted or the more accessible carbon atom.

Interpretation Introduction

(b)

Interpretation: The structure of cross-linked polymer B formed from the treatment of A with H2NCH2CH2CH2NH2 is to be stated.

Concept introduction: Epoxides are strained three-membered rings. They undergo anionic polymerization to afford the ring opening, by following the SN2 pathway. The ring opening in an unsymmetrical epoxide takes place at the less substituted or the more accessible carbon atom.

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3. SYNTHESIS. Propose a sequence of synthetic steps (FGI) that convert the starting material (SM) into the Target molecule. For each FGI in your proposed synthesis, specify the reagents / conditions, and draw the product(s) of that FGI. DO NOT INCLUDE the FGI mxn in the answer you submit. If an FGI requires two reagent sets, specify the order in which the reagent sets are added, e.g., i) Hg(OAc)2 / H₂O; ii) NaBH4/MeOH. Indicate the stereochemistry (if any) of the products of each FGI. FGI 1. Me Starting Material Source of all carbons in the Target molecule (can use multiple copies) Me Me Target molecule + enantiomer
curved arrows are used to illustate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction mechanism steps
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