Logout Open In App
Open In App
Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Chapter 30: Question 30.47 (page 1227)

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

Short Answer

Expert verified

Answer

Mechanism of the reaction

Step by step solution

01

Bisphenol A

The simplest bisphenol synthesized by reacting two phenol molecules with acetone in the presence of acids is bisphenol-A. This organic compound has good solubility in organic solvents but poor solubility in water.

02

About the mechanism

When sulfuric acid is treated with acetone, a carbocation will be formed. This carbocation is treated with phenol that results in a dihydroxy compound.

Formation of dihydroxy compound

03

Addition of second phenol molecule

The obtained dihydroxy compound is treated with acid again, and water is removed. As a result, carbocation is formed. It is treated with another phenol molecule that leads to the formation of bisphenol A. The mechanism is shown below.

Formation of bisphenol A

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.

Start your free trial

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

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

Explain why styrene can be polymerized to polystyrene by all three methods of chain-growth polymerization.

Which method of ionic polymerization-cationic or anionic-is preferred for each monomer? Explain your choices.

(a.)

(b.)

(c.)

(d.)

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.

Researchers at Rutgers University have developed biocompatible polymers that degrade into nonsteroidal anti-inflammatory drugs. For example, the reaction of two equivalents of benzyl salicylate and one equivalent of sebacoyl chloride forms a poly(anhydride ester) called PolyAspirin, which hydrolyzes to salicylic acid (an anti-inflammatory agent) and sebacic acid, which is excreted. This technology can perhaps be used for localized drug delivery at specific sites of injury. What is the structure of PolyAspirin?
See all solutions

Recommended explanations on Chemistry Textbooks

Kinetics

Read Explanation

Nuclear Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Making Measurements

Read Explanation

Chemical Reactions

Read Explanation

Physical Chemistry

Read Explanation
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