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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

Would you expect allene, H2C=C=CH2, to show a UV absorption in

the 200 to 400 nm range? Explain.

The following ultraviolet absorption maxima have been measured:

1,3-Butadiene 217 nm

2-Methyl-1,3-butadiene 220 nm

1,3-Pentadiene 223 nm

2,3-Dimethyl-1,3-butadiene 226 nm

2,4-Hexadiene227 nm

2,4-Dimethyl-1,3-pentadiene 232 nm

2,5-Dimethyl-2,4-hexadiene 240 nm

What conclusion can you draw about the effect of alkyl substitution on

UV absorption maxima? Approximately what effect does each added

alkyl group have?

Dimethyl butynedioate undergoes a Diels-Alder reaction with (2E,4E)-2,4-hexadiene. Show the structure and stereochemistry of the product.

Show the mechanism of the acid-catalyzed polymerization of 1,3-butadiene.

Give IUPAC names for the following compounds:
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