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Chapter 30: Question 30.40 (page 1227)

Cationic polymerization of 3-phenylpropene (CH2=CHCH2PH)affords A as the major product rather than B. Draw a stepwise mechanism to account for this observation.

Short Answer

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Answer

Mechanism

Step by step solution

01

Carbocation Stability

Carbocation stability can be explained based on hyperconjugation and resonance. The stability order of carbocations is:

Benzyl>allyl>tertiary>secondary> primary.

02

The structure of 3-phenylpropene

The molecular structure of 3-phenylpropene is as shown:

3-phenylpropene

The possible cations formed from this compound on reaction with mild acid is

The types of carbocation intermediates formed

As structure “I” is a benzylic cation, it is more stable than II.

03

The cationic polymerization of the given monomer

The cationic polymerization of the given monomer forms the more stable benzylic intermediate and predominantly forms polymer A. The cationic polymerization of the given monomer forms the more stable benzylic intermediate and predominantly forms polymer A.

Cationic polymerization

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Most popular questions from this chapter

Lexan can also be prepared by the acid-catalyzed reaction of diphenyl carbonate with bisphenol A. Draw a stepwise mechanism for this process.

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

(a.)

(b.)

Question:Kevlar (Section 30.6A) is a very stiff polymer because its backbone contains many aromatic rings and its polymer chains are extensively hydrogen bonded to each other. Draw a short segment of two Kevlar chains, and indicate how the chains are hydrogen bonded to each other.

Melmac, a thermosetting polymer formed from melamine and formaldehyde (CH2=O), is used to make dishes and countertops. Draw a stepwise mechanism for the condensation of one mole of formaldehyde with two moles of melamine, which begins the synthesis of Melmac.

Explain the differences observed in the Tg and Tm values for each pair of polymers:

(a) polyester A and PET;

(b) polyester A and nylon 6,6.

(c) How would you expect the Tm value for Kevlar (Section 30.6A) to compare with the Tm value for nylon 6,6? Explain your prediction.
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