Polycarbonates (Section 29.5C) are also formed by using a nucleophilic aromatic substitution route (Section 22.3B) involving aromatic difluoro monomers and carbonate ion. Propose a mechanism for this reaction.

Short Answer

Expert verified
Question: Describe the mechanism of polycarbonate formation via nucleophilic aromatic substitution. Answer: The mechanism of polycarbonate formation via nucleophilic aromatic substitution involves four steps: 1) nucleophilic attack of a carbonate ion on an electrophilic carbon in the aromatic ring, forming a sigma complex, 2) loss of a fluoride ion, restoring the aromatic ring's structure, 3) formation of a carbonate linkage (O-C-O) between two aromatic rings, and 4) polymerization with new difluoroaromatic monomers and carbonate ions, extending the polycarbonate chain. This mechanism leads to the formation of polycarbonates through nucleophilic attack, loss of fluoride ions, and polymerization.

Step by step solution

01

Nucleophilic attack on the aromatic ring

The reaction starts with the nucleophile (carbonate ion) attacking the electrophilic carbon in the aromatic ring. This leads to the formation of a sigma complex where the negative charge is delocalized over the ring system.
02

Loss of a fluoride ion and formation of a new aromatic ring

Now, one of the fluoride ions leaves the sigma complex, and the aromaticity of the ring is restored. This results in the formation of an intermediate with a new single bond between the carbonate ion and the formerly electrophilic carbon atom in the aromatic ring.
03

Formation of a carbonate linkage between two aromatic rings

The intermediate molecule now reacts with another difluoroaromatic monomer through nucleophilic attack, following the same mechanism as in step 1. As a result, a carbonate linkage (O-C-O) is formed between the two aromatic rings, which is the basic structural unit of polycarbonates.
04

Polymerization

The reaction continues to occur with new difluoroaromatic monomers and carbonate ions, which attack the intermediate products and lead to the formation of a longer polycarbonate chain. This process, known as polymerization, proceeds until the desired molecular weight of the polymeric material is attained. In summary, the nucleophilic aromatic substitution mechanism involves the nucleophilic attack of carbonate ions on difluoroaromatic monomers, followed by loss of fluoride ions and formation of carbonate linkages between aromatic rings, which eventually leads to the formation of polycarbonates through polymerization.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free