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Chapter 27: Problem 47

Nylon 66 is produced by the reaction of 1,6 -hexanediamine with adipic acid. A different nylon polymer is obtained if sebacyl chloride is substituted for the adipic acid. What is the basic repeating unit of this nylon structure?

Short Answer

Expert verified
The basic repeating unit of this nylon structure is \( -(NH-(CH2)6-NH-CO-(CH2)8-CO)- \)

Step by step solution

01

Identify the Reactants

The reactants are 1,6-hexanediamine, which is a diamine compound, and sebacyl chloride, a diacid chloride. The structure of 1,6-hexanediamine is H2N-(CH2)6-NH2 and sebacyl chloride is ClOC-(CH2)8-COCl. Notice the 'amine' groups \(NH2\) present in the diamine and the 'acid chloride' groups \(COCl\) in the diacid chloride.
02

Understand the Polymerization Process

During the polymerization process, a hydrogen atom from the amine group of the diamine reacts with the chloride of the acid chloride group, forming a molecule of HCl and linking the two reactants together through an amide linkage, -NH-CO-.
03

Formulate the Basic Repeating Unit

The reaction won't just happen once, but will repeat many times, leading to the formation of a polymer. The basic repeating unit of this nylon structure, given the reactants, will be HN-(CH2)6-NH-CO-(CH2)8-CO.
04

Simplify the Basic Repeating Unit

In the final step, simplify the basic repeating unit and remove the elements that will not repeat in the polymer chain. This gives the basic repeating unit in the nylon as -(NH-(CH2)6-NH-CO-(CH2)8-CO)-.

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Describe what is meant by each of the following reaction types, and illustrate with an example: (a) nucleophilic substitution reaction; (b) electrophilic substitution reaction; (c) addition reaction; (d) elimination reaction; (e) rearrangement reaction.

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Write equations for the substitution reaction of \(n\) -bromopentane, a typical primary haloalkane with the following reagents: (a) \(\mathrm{NaN}_{3};\) (b) \(\mathrm{N}\left(\mathrm{CH}_{3}\right)_{3};\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CNa};\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SNa}\).

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