Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 27.3, Problem 4P
Interpretation Introduction
Interpretation:
The mechanism for the formation of a segment of poly vinyl chloride that contains three units of vinyl chloride and is initiated by hydrogen peroxide should be given.
Concept Introduction:
Monomers combine together to form polymers. Monomers are the repeating units of small molecules which link together to form polymers and the process is called as
Two types of polymers:
- Synthetic and biopolymers.
- DNA is an example for biopolymer and these type of polymers are synthesized by cells.
- Polymers synthesized by scientists are called
synthetic polymers and some examples are nylon, polyester etc.
Two types of synthetic polymers:
- Chain-growth
polymers or addition polymers and Step-growthpolymers or Condensation polymers. - Chain growth polymers are formed by the monomer addition to the end of a growing chain.
- Step-growth polymers are formed by combining monomers by removing small molecules of water or alcohol.
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Research in the “unzipping” of poly(vinyl chloride) indicates that certain defects in the polymer contribute to the rate of unzipping. These defects are arrangements of atoms that are different from the arrangements in the repeating unit shown in the condensed formula. Researchers have found that defects involving allylic chlorides and tertiary chlorides, specifically, promote the reaction. Review the mechanism for the unzipping and explain this observation.
Draw the mechanism for the production of Nylon, identify the new linkage that has formed as a result of polymerization. What is the name of this linkage in organic chemistry?
Styrene can autoinitiate free radical polymerization and form polystyrene in the absence of an initiator. At temperatures
>100 °C, radicals form due to homolysis of the T bond in the vinyl group. In the study of this reaction, researchers
have found 1,2-diphenylcyclobutane in samples of heated styrene. The following mechanism for the formation of
1,2-diphenylcyclobutane has been proposed:
Step 1: Homolysis of the vinyl T bond in a styrene molecule
Step 2: Homolysis of the vinyl T bond in a second styrene molecule
Step 3: Tail-to-tail addition of the radicals from Steps 1 and 2
Step 4: Radical coupling of the diradical formed in Step 3
(a) Use curved arrow notation to show the steps in this mechanism.
(b) Are the steps in this mechanism consistent with those for free radical polymerization?
(c) Why is the use of an initiator such as benzoyl peroxide more efficient in the synthesis of polystyrene than
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Chapter 27 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 27.3 - Prob. 1PCh. 27.3 - Prob. 2PCh. 27.3 - Prob. 3PCh. 27.3 - Prob. 4PCh. 27.3 - Prob. 5PCh. 27.3 - Prob. 6PCh. 27.4 - Prob. 7PCh. 27.5 - Rank the following groups of monomers from most...Ch. 27.5 - Why does methyl methacrylate not undergo cationic...Ch. 27.6 - Prob. 10P
Ch. 27.6 - Explain why, when propylene oxide undergoes...Ch. 27.6 - Which monomer and which type of initiator can you...Ch. 27.6 - Prob. 13PCh. 27.8 - Draw a short segment of gutta-percha.Ch. 27.8 - Prob. 15PCh. 27.11 - Prob. 16PCh. 27.11 - Write an equation that explains what happens if a...Ch. 27.11 - What happens to polyester slacks if aqueous NaOH...Ch. 27.11 - a. Propose a mechanism for the formation of the...Ch. 27.11 - Explain why, when a small amount of glycerol is...Ch. 27.12 - Propose a mechanism for the formation of melmac.Ch. 27.12 - Prob. 22PCh. 27.13 - Prob. 23PCh. 27 - Draw short segments of the polymers obtained from...Ch. 27 - Prob. 25PCh. 27 - Prob. 26PCh. 27 - Draw the structure of the monomer or monomers used...Ch. 27 - Prob. 28PCh. 27 - Draw short segments of the polymers obtained from...Ch. 27 - Quiana is a synthetic fabric that feels very much...Ch. 27 - Prob. 31PCh. 27 - Prob. 32PCh. 27 - Prob. 33PCh. 27 - Poly(vinyl alcohol) is a polymer used to make...Ch. 27 - Five different repeating units are found in the...Ch. 27 - Prob. 37PCh. 27 - A particularly strong and rigid polyester used for...Ch. 27 - Prob. 39PCh. 27 - Which Monomer gives a greater yield of polymer,...Ch. 27 - Prob. 41PCh. 27 - Prob. 42PCh. 27 - Why do vinyl raincoats become brittle as they get...Ch. 27 - The polymer shown below is synthesized by...Ch. 27 - Prob. 45PCh. 27 - How can head-to-head poly(vinyl bromide) be...Ch. 27 - Delrin (polyoxymethylene) is a tough...
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