Chapter 30: Question 30.8 (page 1206)

Draw a stepwise mechanism for the conversion of acrylonitrile (CH2=CHCN)to polyacrylonitrile, -[CH2=CHCN]n, using butyllithium(BuLi) as the initiator and CO2 as the electrophile to terminate the chain.

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Step by step solution

01

Stepwise reaction

A stepwise reaction constitutes a reaction comprising two or more steps in the mechanism. An example of a stepwise reaction is free-radical polymerization, which includes initiation, propagation, and termination.

02

Polymerization

Polymerization constitutes a process where small molecules called monomers link to form a network molecule called polymers. The molecules created from the polymerization comprises of linear or branched structure.

03

Stepwise mechanism for the conversion of acrylonitrile to polyacrylonitrile

The general steps involved in converting acrylonitrile to polyacrylonitrile are initiation, propagation, and termination.

In the first step, the creation of carbanion happens by the nucleophilic addition of butyl lithium.

Initiation step

The second step is propagation in which the carbanion incorporates another monomer.

Propagation step

The third step is termination, where the incorporation of electrophile stops the chain leading to the formation of poly(vinyl acetate).

Termination step

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Most popular questions from this chapter

(a) Explain why poly(vinyl alcohol) cannot be prepared by the radical polymerization of vinyl alcohol (CH2=CHOH)(b) Devise a stepwise synthesis of poly(vinyl alcohol) from vinyl acetate(CH2=CHOCOCH3)(c) How can poly(vinyl alcohol) be converted to poly(vinyl butyral), a polymer used in windshield safety glass?

Draw a stepwise mechanism for the following reaction, which is used to prepare bisphenol A (BPA), a widely used monomer in polymer synthesis.

Compound A is a novel poly(ester amide) copolymer that can be used as a bioabsorbable coating for the controlled release of drugs. A is a copolymer of four monomers, two of which are amino acids or amino acid derivatives. The body’s enzymes recognize the naturally occurring amino acids in the polymer backbone, allowing for the controlled enzymatic breakdown of the polymer and steady release of an encapsulated drug. Identify the four monomers used to synthesize A; then use Figure 29.2 to name the two amino acids.

Poly(ester amide) A

Although chain branching in radical polymerizations can occur by intermolecular H abstraction as shown in Mechanism 30.2, chain branching can also occur by intramolecular H abstraction to form branched polyethylene that contains butyl groups as branches.

a. Draw a stepwise mechanism that illustrates which H must be intramolecularly abstracted to form butyl substituents.

b. Suggest a reason why the abstraction of this H is more facile than the abstraction of other H’s.

What polymer is formed by the anionic polymerization of each monomer?

(a.)

(b.)

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