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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

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Most popular questions from this chapter

Draw the structure of the polymer formed by step-growth polymerization of each monomer or pair of monomers.

(a.)

(b.)

(c.)

(d.)

Draw the mechanism for the radical polymerization of vinyl acetate (CH2=CHOCOCH3) using(CH3)3CO-OC(CH3)3 as the initiator.

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.

Why can’t chemical recycling—that is, the conversion of polymer to monomers and re-conversion of monomers to polymer—be done easily with HDPE and LDPE?

Draw the structure of the three monomers used to prepare polybutyrateadipate terephthalate (PBAT), a biodegradable copolymer sold under the trade name of Ecoflex. Because PBAT has properties similar to low-density polyethylene, it can be used in biodegradable food packaging and plastic bags.

PBAT
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