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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-with drawing groups. 3. The zwitterion formed by addition of water is well solvated in the cyanoacrylate matrix of the glue. 4. Both 1 and 2.

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Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350

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Chapter
Section
BuyFindarrow_forward

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Chapter 29.6, Problem BQ
Textbook Problem
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Why does the weak nucleophile, water, efficiently add to the cyanoacrylate?

  1. 1. Superglue must possess hydroxide as a promoter to initiate the polymerization in the presence of water.
  2. 2. The carbanion formed by nucleophilic addition of water is resonance-stabilized by two electron-with drawing groups.
  3. 3. The zwitterion formed by addition of water is well solvated in the cyanoacrylate matrix of the glue.
  4. 4. Both 1 and 2.

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

Explanation of Solution

Reason for correct option:

The polymerisation involved in the curing of superglue is given by,

In the first step water adds to cyanoacrylate and form an anion.  This carbanion formed is resonance stabilized by presence of two electron withdrawing groups.  Therefore, water adds efficiently to cyanoacrylate...

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Chapter 29 Solutions

Organic Chemistry
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