ORGANIC CHEMISTRY(LL)-W/ACCESS >CUSTOM<
ORGANIC CHEMISTRY(LL)-W/ACCESS >CUSTOM<
10th Edition
ISBN: 9781259917196
Author: Carey
Publisher: MCG CUSTOM
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Chapter 28.7, Problem 5P

Problem 28.5

(a) Write a chemical equation for the reaction in which tert-butoxy radical adds to vinyl chloride to initiate polymerization. Show the flow of electrons with curved arrows.

(b) Repeat part (a) for the polymerization of styrene using AIBN as an initiator.

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Although chain branching in radical polymerizations can occur by intermolecular H abstraction as shown in Mechanism 30.2, chain branching can also occur by intramolecular H abstraction to form branched polyethylene that contains butyl groups as branches.a. Draw a stepwise mechanism that illustrates which H must be intramolecularly abstracted to form butyl substituents.b. Suggest a reason why the abstraction of this H is more facile than the abstraction of other H’s.
Consider monomers A–C. (a) Rank the monomers in order of increasingreactivity in cationic polymerization. (b) Rank the monomers in order ofincreasing reactivity in anionic polymerization.
Although chain branching in radical polymerizations can occur by intermolecular H abstraction as shown in Mechanism 28.2, chain branching can also occur by intramolecular H abstraction to form branched polyethylene that contains butyl groups as branches.a. Draw a stepwise mechanism that illustrates which H must be intramolecularly abstracted to form butyl substituents. b. Suggest a reason why the abstraction of this H is more facile than the abstraction of other H's.
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