/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Problem 166 Polycarbonates are a class of th... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Polycarbonates are a class of thermoplastic polymers that are used in the plastic lenses of eyeglasses and in the shells of bicycle helmets. A polycarbonate is made from the reaction of bisphenol A (BPA) with phosgene (COCl_): Phenol \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\right)\) is used to terminate the polymer (stop its growth). a. Draw the structure of the polycarbonate chain formed from the above reaction. b. Is this reaction a condensation or an addition polymerization?

Short Answer

Expert verified
a. The structure of the polycarbonate chain formed from the reaction is: \[ \text{O}\mathrm{C}_{6}\mathrm{H}_{4}\text{C}(\text{H}_2)_2\mathrm{C}_{6}\mathrm{H}_{4}\text{OC(O)C}_{n}\text{Phenol} \] b. The reaction is a condensation polymerization.

Step by step solution

01

Identify the reactants and their structures

First, we need to identify the structures of the reactants involved in the reaction, which are bisphenol A (BPA) and phosgene (COCl2). Bisphenol A (BPA) structure: \[ \text{H}\text{O}\mathrm{C}_{6}\mathrm{H}_{4}\text{C}(\text{H}_2)_2\mathrm{C}_{6}\mathrm{H}_{4}\text{OH} \] Phosgene (COCl2) structure: \[ \mathrm{Cl}\text{C}(\text{O})\mathrm{Cl} \] Phenol (C6H5OH) structure: \[ \mathrm{C}_{6}\mathrm{H}_{5}\text{OH} \]
02

Draw the structure of the polycarbonate chain formed from the reaction

The reaction between bisphenol A and phosgene will involve the formation of ester links between bisphenol A molecules with the loss of HCl. The general structure of the polycarbonate chain can be represented as: \[ \text{O}\mathrm{C}_{6}\mathrm{H}_{4}\text{C}(\text{H}_2)_2\mathrm{C}_{6}\mathrm{H}_{4}\text{OC(O)C}_{n}\text{Phenol} \] The phenol molecule terminates the polymer chain.
03

Determine the type of polymerization

Since the reaction involves the formation of ester links with the loss of HCl, we know that it is a condensation reaction. In condensation polymerization, a small molecule is eliminated during the process, such as water or HCl. In contrast, addition polymerization does not involve the elimination of small molecules. Therefore, the reaction is a condensation polymerization. In conclusion: a. The structure of the polycarbonate chain formed from the reaction is: \[ \text{O}\mathrm{C}_{6}\mathrm{H}_{4}\text{C}(\text{H}_2)_2\mathrm{C}_{6}\mathrm{H}_{4}\text{OC(O)C}_{n}\text{Phenol} \] b. The reaction is a condensation 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 91Ó°ÊÓ!

Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Condensation Reaction
In the realm of chemistry, a condensation reaction is a process where two molecules join together, resulting in the loss of a small molecule. This small molecule is often water, but it can also be substances like hydrogen chloride (HCl).
Condensation reactions are crucial in forming complex structures like polymers, where they enable the linking of monomer units. For example, in the polymerization of polycarbonates, bisphenol A reacts with phosgene, and HCl is released during the formation of ester bonds. This reaction showcases the essence of condensation, as the addition of each monomer causes the release of a small molecule.
  • Establishes ester linkage
  • Involves loss of small molecules like HCl
  • Connects monomers into polymers
Understanding condensation reactions is key in fields ranging from plastics to biochemistry. They provide insights into how large, stable molecules such as polymers and proteins are formed through the interaction of simpler components.
Bisphenol A
Bisphenol A, commonly abbreviated as BPA, is an important monomer in the production of polycarbonate plastics. It is a type of diol, specifically a diphenylmethane derivative, which means its structure contains two phenol groups connected by a methylene bridge.
This structure allows BPA to easily form ester linkages with reactive partners in chemical reactions. In the production of polycarbonates, BPA's dual phenol groups facilitate its reaction with phosgene, leading to polymer formation. The resulting polycarbonate material is valued for its clarity and impact resistance, making it suitable for products like eyewear lenses and protective gear. Key points about BPA include:
  • High reactivity due to two phenol groups
  • Forms strong, durable polymers
  • Contributes to the plastic's optical clarity
Despite its usefulness, BPA's safety has been debated, considering the possibility of leaching into substances and acting as an endocrine disruptor.
Phosgene
Phosgene is a simple but reactive chemical compound used extensively in industrial applications. Its formula is COCl2, consisting of one carbonyl group (C=O) flanked by two chlorine atoms.
This reactive nature makes phosgene suitable for creating important industrial materials, although it must be handled with caution due to its toxicity. In polymer chemistry, phosgene is instrumental in the synthesis of polycarbonates. It reacts with bisphenol A to form ester linkages, which are the backbone of the resultant polymer chains. This reaction releases hydrogen chloride (HCl), a characteristic of condensation polymerizations. Phosgene's key features include:
  • Reactivity with diols to form esters
  • Used in making polycarbonate plastics
  • Presents toxicity, requiring careful handling
While beneficial for producing various chemical products, its historical use as a chemical warfare agent underscores the need for careful management in industrial processes.
Polymer Chain Structure
Polycarbonate polymers have a unique chain structure characterized by the repeating units joined by ester linkages. Understanding this structure offers insight into why polycarbonates have specific physical properties like durability and optical transparency.
Each polymer chain in polycarbonate production is composed of repeating units formed from bisphenol A and phosgene. The chain grows through condensation reactions, where the bisphenol A reacts with phosgene, forming ester linkages and releasing HCl. The polymer chain is terminated by phenol, effectively capping the polymer and halting further growth.
  • Repeating units provide strength
  • Ester linkages confer stability and flexibility
  • Phenol acts as a chain terminator
This structured stability explains why polycarbonates are suitable for demanding applications such as impact-resistant eyewear and high-strength engineering components.

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

Is the primary, secondary, or tertiary structure of a protein changed by denaturation?

Polychlorinated dibenzo-p-dioxins (PCDDs) are highly toxic substances that are present in trace amounts as by-products of some chemical manufacturing processes. They have been implicated in a number of environmental incidents—for example, the chemical contamination at Love Canal and the herbicide spraying in Vietnam. The structure of dibenzo-pdioxin, along with the customary numbering convention, is The most toxic PCDD is 2,3,7,8-tetrachloro-dibenzo-p-dioxin. Draw the structure of this compound. Also draw the structures of two other isomers containing four chlorine atoms.

Give the structure of each of the following aromatic hydrocarbons. $$ \begin{array}{ll}{\text { a. } o \text { -ethyltoluene }} & {\text { c. } m \text { -diethylbenzene }} \\ {\text { b. } p \text { -di-tert-butylbenzene }} & {\text { d. } 1 \text { -phenyl-2-butene }}\end{array} $$

Give the structure for each of the following. a. 4-methyl-1-pentyne b. 2,3,3-trimethyl-1-hexene c. 3-ethyl-4-decene

In the presence of light, chlorine can substitute for one (or more) of the hydrogens in an alkane. For the following reactions, draw the possible monochlorination products. $$ 2,2 \text { -dimethylpropane }+\mathrm{Cl}_{2} \longrightarrow $$ $$ 1,3 \text { -dimethylcyclobutane }+\mathrm{Cl}_{2} \stackrel{\mathrm{hn}}{\longrightarrow} $$ $$ 2,3 \text { -dimethylbutane }+\mathrm{Cl}_{2} \stackrel{\mathrm{w}}{\longrightarrow} $$

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.