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Chapter 15: Q26. (page 570)

Question: (a)Draw the structure of polystyrene, the chapter-opening molecule, which is formed by polymerizing the monomer styrene, C6H5CH=CH2. (b) What monomer is used to form poly(vinyl acetate), a polymer used in paints and adhesives?

Short Answer

Expert verified

Answer

(a)

(b)

Step by step solution

01

Polystyrene

Polystyrene is generated from the monomer termed styrene. It is a kind of thermoplastic polymer and is frequently employed for several purposes in the food industry.

02

Polyvinyl acetate

Polyvinyl acetate is known by several names like wood glue, carpenter’s glue, etc. Polymers like polyvinyl alcohol can be made from polyvinyl acetate.

03

Structure of polystyrene and the monomer of polyvinyl acetate

(a) The repeated bonding of a monomer leads to the formation of polymers. They are formed through condensation or addition reactions. The structure of polystyrene formed by polymerizing styrene can be given as:

Structure of polystyrene that is formed by polymerizing styrene

The structure of polystyrene can be given as:

Structure of polystyrene

(b)The monomer required for the formation of poly(vinyl acetate) can be given as:

Monomer required for the formation of poly(vinyl acetate

The structure of poly(vinyl acetate) can be given as:

Structure of poly(vinyl acetate)

The polymerization of vinyl acetate leads to the formation of poly(vinyl acetate) as shown below:

Polymerization of vinyl acetate

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Most popular questions from this chapter

Question: Which C-H bond in each compound most readily broken during radical halogenation?

a.

b.

c.

Question: As we will learn in Chapter 30, styrene derivatives such as A can be polymerized by way of cationic rather than radical intermediates. Cationic polymerization is an example of electrophilic addition to an alkene involving carbocations.

a. Draw a short segment of the polymer formed by the polymerization of A.

b. Why does A react faster than styrene (C6H5CH=CH2)in a cationic polymerization?

Question: PGF2α (Section 4.15) is synthesized in cells from arachidonic acid C20H32O2 using a cyclooxygenase enzyme that catalyzes a multistep radical pathway. Part of this process involves the conversion of radical A to PGG2, an unstable intermediate, which is then transformed to PGF2α and other prostaglandins. Draw a stepwise mechanism for the conversion of A to PGG2 . (Hint: The mechanism begins with radical addition to a carbon-carbon double bond to form a resonance-stabilized radical.

Question: Draw the monochlorination products formed when each compound is heated with Cl2. Include the stereochemistry at any stereogenic center.

a.

b.

c.

d.

Question: When 3,3-dimethylbut-1-ene is treated with HBr alone, the major product is 2-bromo-2,3- dimethylbutane. When the same alkene is treated with HBr and peroxide, the sole product is 1-bromo-3,3-dimethylbutane. Explain these results by referring to the mechanisms.

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