Organic Chemistry, - Standalone Book 2nd Edition solutions

Organic Chemistry, - Standalone Book 2
Draw and name the polymer that results when each of the following monomers undergoes polymerization: OAc C C H H H (a) Vinyl acetate Br C C H H H (b) Vinyl bromide CH2CH3 C C H H H (c) a-Butylene

Organic Chemistry, - Standalone Book 2
Sodium polyacrylate is a synthetic polymer used in diapers, because of its ability to absorb several hundred times its own mass of water. This extraordinary polymer is made from another polymer, poly(methyl acrylate), via hydrolysis of the ester groups. Draw and name the monomer used to make poly(met

Organic Chemistry, - Standalone Book 2
Draw a region of an alternating copolymer constructed from styrene and ethylene.

Organic Chemistry, - Standalone Book 2
Draw a region of a block copolymer constructed from propylene and vinyl chloride.

Organic Chemistry, - Standalone Book 2
Identify the monomers required to make the following alternating copolymer: CC H H Ph H C C CH3 H CH3 H n

Organic Chemistry, - Standalone Book 2
Determine whether preparation of each of the following polymers would best be achieved via cationic addition or anionic addition: CN CN CN CN (a) OMe OMe OMe OMe (b) (c) OAc OAc OAc OAc (d) NO2 NO2 NO2 NO2 (e) CCl3 CCl3 CCl3 CCl3 (f)

Organic Chemistry, - Standalone Book 2
Arrange the following monomers in order of reactivity toward cationic polymerization: OAc NO2 CH3

Organic Chemistry, - Standalone Book 2
Arrange the following monomers in order of reactivity toward anionic polymerization: NO2 Cl

Organic Chemistry, - Standalone Book 2
Many monomers that readily undergo cationic polymerization, such as isobutylene, will not readily undergo anionic polymerization. Styrene, however, can be effectively polymerized via cationic, anionic, or radical addition. Explain.

Organic Chemistry, - Standalone Book 2
A tube of superglue will harden if it remains open too long in a humid environment. Draw a mechanism that shows how superglue polymerizes in the presence of atmospheric moisture. When drawing your mechanism, make sure to draw the initiation step, at least two propagation steps, and a termination step

Organic Chemistry, - Standalone Book 2
Draw the mechanism of formation of PET in acidic conditions. It might be helpful to first review the mechanism for the Fischer esterification process.

Organic Chemistry, - Standalone Book 2
Draw the polymer that would be generated from the acidcatalyzed reaction between oxalic acid and resorcinol. Oxalic acid HO O OH O HO OH Resorcinol [H+]

Organic Chemistry, - Standalone Book 2
Kevlar is a condensation polymer used in the manufacture of bulletproof vests. Identify the monomers required for the preparation of Kevlar. N O O N N O O N H H H H Kevlar

Organic Chemistry, - Standalone Book 2
Identify the monomers required to make each of the following condensation polymers: O O O O O O O O (a) O O O O O O O O O

Organic Chemistry, - Standalone Book 2
Identify the condensation polymer that would be produced when phosgene is treated with 1,4-butanediol.

Organic Chemistry, - Standalone Book 2
Nylon 6 is a polyamide used in the manufacture of ropes. It can be prepared via hydrolysis of e-caprolactam to form e-aminocaproic acid followed by acid-catalyzed polymerization. e-Caprolactam N O H HO O NH2 e-Aminocaproic acid Nylon 6 Hydrolysis Polymerization (a) Draw the structure of Nylon 6. (b)

Organic Chemistry, - Standalone Book 2
Would these pairs of monomers form chain-growth or step-growth polymers? Cl O Cl O H2N NH2 (a) + Cl CN (b) +

Organic Chemistry, - Standalone Book 2
Should this polymer be classified as a chain-growth polymer or a step-growth polymer? O O O O O O O O O

Organic Chemistry, - Standalone Book 2
Polyisobutylene cannot be described as isotactic, syndiotactic, or atactic. Explain.

Organic Chemistry, - Standalone Book 2
Polyethylene is used to make Ziploc bags and folding tables. Identify which of these applications is most likely to be made from HDPE and which is most likely to be made from LDPE.

Organic Chemistry, - Standalone Book 2
Propose a mechanism for the acid-catalyzed hydrolysis of PET to regenerate the monomers terephthalic acid and ethylene glycol.

Organic Chemistry, - Standalone Book 2
Draw and name the polymer that results when each of the following monomers undergoes polymerization: C C NO2 H H H (a) Nitroethylene C C CN H H H (b) Acrylonitrile C C F H F H (c) Vinylidene fluoride

Organic Chemistry, - Standalone Book 2
Kodel is a synthetic polyester with the following structure: Kodel n O O O O (a) Identify what monomers you would use to make Kodel. (b) Would you use acidic conditions or basic conditions for this polymerization process?

Organic Chemistry, - Standalone Book 2
Draw the structures of the monomers required to make the following alternating copolymer: CC Ph H Ph H C C Cl H Cl H n

Organic Chemistry, - Standalone Book 2
Draw a region of a block copolymer constructed from isobutylene and styrene.

Organic Chemistry, - Standalone Book 2
Draw a region of an alternating copolymer constructed from vinyl chloride and ethylene.

Organic Chemistry, - Standalone Book 2
Identify which of the following monomers would be most reactive toward cationic polymerization: OAc CN Cl

Organic Chemistry, - Standalone Book 2
Identify which of the following monomers would be most reactive toward anionic polymerization: OAc CN CH3

Organic Chemistry, - Standalone Book 2
Identify the repeating unit of the polymer formed from each of the following reactions and then determine whether the polymer is a chain-growth or a step-growth polymer. ? [H+] (a) CO2H CO2H NH2 NH2 + N N C O C O OH OH (b) + ? HO HO Cl Cl O (c)

Organic Chemistry, - Standalone Book 2
Quiana is a synthetic polymer that can be used to make fabric that mimics the texture of silk. It can be prepared from the following monomers: H2N NH2 HO OH O O + (a) Draw the structure of Quiana. (b) Is Quiana a polyester, a polyamide, a polycarbonate, or a polyurethane? (c) Is Quiana a step-growth

Organic Chemistry, - Standalone Book 2
Draw the monomer(s) required to make each of the following condensation polymers: N O H N O H O N H (a) O O O O O O (b

Organic Chemistry, - Standalone Book 2
Draw the condensation polymer produced when 1,4-cyclohexanediol is treated with phosgene.

Organic Chemistry, - Standalone Book 2
Determine whether the following pairs of monomers would form chain-growth polymers or step-growth polymers. HO O OH O HO OH (a) + NO2 Ph (b)

Organic Chemistry, - Standalone Book 2
Nitroethylene undergoes anionic polymerization so rapidly that it is difficult to isolate nitroethylene without it polymerizing. Explain.

Organic Chemistry, - Standalone Book 2
Explain why vinyl shower curtains develop cracks over time.

Organic Chemistry, - Standalone Book 2
Polyformaldehyde, sold under the trade name Delrin, is a strong polymer used in the manufacture of many guitar picks. It is prepared via the acid-catalyzed polymerization of formaldehyde. (a) Draw the structure of polyformaldehyde. (b) Would you describe polyformaldehyde as a polyether or a polyester

Organic Chemistry, - Standalone Book 2
The following monomer can be polymerized under either acidic or basic conditions. Explain. CN OMe

Organic Chemistry, - Standalone Book 2
Anionic polymerization of para-nitrostyrene occurs much more rapidly than anionic polymerization of styrene. Explain this difference in rate.

Organic Chemistry, - Standalone Book 2
Cationic polymerization of para-methoxystyrene occurs much more rapidly than cationic polymerization of styrene. Explain this difference in rate.

Organic Chemistry, - Standalone Book 2
Cationic polymerization of para-methoxystyrene occurs much more rapidly than cationic polymerization of meta-methoxystyrene. Explain this difference in rate.

Organic Chemistry, - Standalone Book 2
Draw segments of the following polymers, indicating the stereochemistry with wedges and/or dashes. (a) Syndiotactic poly(vinyl chloride) (b) Isotactic polystyrene

Organic Chemistry, - Standalone Book 2
Consider the structure of the following polymer: O O n N O N H H O (a) Draw the monomers you would use to prepare this polymer. (b) Determine whether this polymer is a step-growth polymer or a chain-growth polymer. (c) Determine whether this polymer is an addition polymer or a condensation polymer.

Organic Chemistry, - Standalone Book 2
Draw the polymer that is expected when the following monomers react under acidic conditions. You may find it helpful to review Section 20.6. O O NH2 + H2N H2O ?

Organic Chemistry, - Standalone Book 2
As described in the Practically Speaking box in Section 27.7, poly(vinyl alcohol) is used as a precursor to make PVB for use in automobile windshields. Poly(vinyl alcohol) can be prepared by polymerizing vinyl acetate and then removing the acetate groups via hydrolysis. OAc Vinyl acetate Poly(vinyl a

Organic Chemistry, - Standalone Book 2
When a solution of aqueous sodium hydroxide is spilled on polyester clothing, a hole develops in the fabric. Describe how the polyester is destroyed.

Organic Chemistry, - Standalone Book 2
When 3-methyl-1-butene is treated with a catalytic amount of BF3 and H2O, a cationic polymerization process occurs, but the expected homopolymer is not formed. Instead, a random copolymer is obtained. (a) Explain why there are two different repeating units. (b) Draw a segment of the random copolymer

Organic Chemistry, - Standalone Book 2
When ethylene oxide is treated with a strong nucleophile, the epoxide ring is opened to form an alkoxide ion that can function as a nucleophile to attack another molecule of ethylene oxide. This process repeats itself, and a polymer is formed. O Ethylene oxide Nuc O O O Poly(ethylene oxide) Nuc @ The

Organic Chemistry, - Standalone Book 2
Using vinyl acetate as your only source of carbon atoms, design a synthesis for the following polymer: OOOO O O OAc Vinyl acetate

Organic Chemistry, - Standalone Book 2
The following compound was isolated from nerve cells: O O O O O (a) Describe how this compound differs in structure from fats and oils. (b) Three products are obtained when this compound is hydrolyzed with aqueous sodium hydroxide. Draw the structures of all three products. (c) Four products are obta