Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 29.6, Problem BQ
Interpretation Introduction

Interpretation:

Among the given terms, the term that explains reason for addition of water to cyanoacrylate has to be identified.

Concept introduction:

Anionic Polymerizations:  It can be initiated by addition of a nucleophile to an activated

Alkene.  The most common nucleophiles used for this purpose are metal alkyls such as methyl- and sec-butyllithium. The newly formed carbanion then acts as a nucleophile and adds to another monomer unit, and the propagation continues.

Organic Chemistry, Chapter 29.6, Problem BQ

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Why does the weak nucleophile, water, efficiently add to the cyanoacrylate? 1. Superglue must possess hydroxide as a promoter to initiate the polymerization in the presence of water. 2. The carbanion formed by nucleophilic addition of water is resonance-stabilized by two electron-withdrawing groups. 3. The zwitterion formed by addition of water is well solvated in the cyanoacrylate matrix of the glue. 4. Both 1 and 2.
6. Nylon 6 is commercially produced via the hydrolytic polymerization of E-caprolactam (azepan-2-one). The mechanism can occur via chain-growth and step-growth mechanisms. Draw these two mechanisms and explain which is expected to predominate.
Which illustrates a random co-polymer? а. b. wan d.
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