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Chapter 14: Q 14-14-60 E (page 447)

Adiponitrile, a starting material used in the manufacture of nylon, can be prepared in three steps from 1,3-butadiene. How would you carry out this synthesis?

Short Answer

Expert verified

The first step of the three is-

Step by step solution

01

Introduction

Adiponitrile is an organic compound which is a precursor used for polymer nylon. Nylon is a synthetic polymer made up of polyamides. It is a silk like thermoplastic made from petroleum which can be melted, can be processed into fibres, films or shapes.

02

Addition, Nucleophilic substitution, Catalytic hydrogenation

First step is the addition of on 1,4 positions to form 1,4-dibromo-2-butene.

After this, 1,4-dibromo-2-butene undergoes nucleophilic substitution with NaCN (SN2)

The product then forms Adiponitrile by undergoing catalytic hydrogenation.

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Most popular questions from this chapter

Predict the products of the following Diels-Alder reaction:

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Show the product of the Diels鈥揂lder reaction of the following dienewith 3-buten-2-one, H2C=CHCOCH3. Make sure you show the fullstereochemistry of the reaction product.

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Di-tert-butyl-1,3-butadiene does not undergo Diels-Alder reactions. Explain.
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