Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 26.2B, Problem 26.6P
Chain branching occurs in cationic
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Chain branching occurs in cationic polymerization much as it does in free-radical polymerization. Propose a mechanism to show how branching occurs in the cationic polymerization of styrene. Suggest why isobutylene might be a better monomer for cationic polymerization than styrene.
Chain branching is not as common with anionic polymerization as it is with free-radical polymerization and cationic polymerization. Propose a mechanism for chain branching in the polymerization of acrylonitrile.
When certain cycloalkenes are used in metathesis reactions, ringopening metathesis polymerization (ROMP) occurs to form a highmolecular- weight polymer, as shown with cyclopentene as the starting material. The reaction is driven to completion by relief of strain in the cycloalkene.What products are formed by ring-opening metathesis polymerization of each alkene?
Chapter 26 Solutions
Organic Chemistry (9th Edition)
Ch. 26.2A - Show the intermediate that would result if the...Ch. 26.2A - Prob. 26.2PCh. 26.2A - Prob. 26.3PCh. 26.2B - Prob. 26.4PCh. 26.2B - Prob. 26.5PCh. 26.2B - Chain branching occurs in cationic polymerization...Ch. 26.2C - Prob. 26.7PCh. 26.2C - Prob. 26.8PCh. 26.2C - Chain branching is not as common with anionic...Ch. 26.3 - Prob. 26.10P
Ch. 26.5 - Prob. 26.11PCh. 26.6 - Prob. 26.12PCh. 26.7A - Prob. 26.13PCh. 26.7B - Prob. 26.14PCh. 26.7B - Prob. 26.15PCh. 26.7C - a. Propose a mechanism for the reaction of...Ch. 26.7C - Prob. 26.17PCh. 26.7D - Prob. 26.18PCh. 26.7D - Prob. 26.19PCh. 26.7D - Prob. 26.20PCh. 26 - Prob. 26.21SPCh. 26 - Prob. 26.22SPCh. 26 - Poly(trimethylene carbamate) is used in...Ch. 26 - Prob. 26.24SPCh. 26 - Urylon fibers are used in premium fishing nets...Ch. 26 - Prob. 26.26SPCh. 26 - Prob. 26.27SPCh. 26 - Polyoxymethylene (polyformaldehyde) is the tough,...Ch. 26 - Prob. 26.29SPCh. 26 - Prob. 26.30SPCh. 26 - Prob. 26.31SPCh. 26 - Prob. 26.32SPCh. 26 - Prob. 26.33SPCh. 26 - Prob. 26.34SPCh. 26 - The polyester named Lactomer is an alternating...Ch. 26 - Prob. 26.36SP
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- Explain why acrylonitrile (CH2 = CHCN) undergoes cationic polymerization more slowly than but-3-enenitrile (CH2 = CHCH2CN).arrow_forwardExplain why a random copolymer is obtained when 3,3-dimethyl-1-butene undergoes cationic polymerization.arrow_forwardA3 Anionic polymerization of styrene is generally known to produce polymers with a narrow molecular weight distribution. Explain the reason for this.arrow_forward
- 1. which cannot be obtained by radical polymerization of its vinyl monomer Poly(ethylene) obtained by polymerization of ethylene monomer Poly(propylene) obtained by polymerization of propylene monomer Poly(vinyl chloride) obtained by polymerization of vinyl chloride monomer Poly(acrylonitrile) obtained by polymerization of acrylonitrile monomerarrow_forwardList the following group of monomers in order of decreasing ability to undergo cationic polymerization.arrow_forwardWhich one of the following initiators can be used for free radical chain-growth polymerization? a) benzoyl peroxide b) BF3 c) CH3CH2CH2CH2Li d) Al(CH2CH3)3, TiCl4arrow_forward
- Chain branching is not as common with anionic polymerization as it is with free-radical polymerization and cationic polymerization. Compare the relative stabilities of the intermediates in this mechanism with those you drew for chain branching in the cationic polymerization of styrene. Explain why chain branching is less common in this anionic polymerization.arrow_forwardMethyl acrylate and methyl methacrylate react with radical initiators (R•) as shown here. The difference in their reactivities in free radical polymerizations is dramatic. For example, methyl acrylate is less reactive with radicals than methyl methacrylate, but free radicals formed from methyl acrylate are more reactive than those formed from methyl methacrylate. In other words, C is more reactive than A, and B is more reactive than D. Explain these observations. Hint: Draw an energy diagram H H R• R-C C• H c=0 H CH3 CH3 Methyl acrylate for the two reactions. H CH3 CH3 R• + R-C C• H c=0 H. CH3 CH3 Methyl methacrylatearrow_forwardDraw the curved arrow mechanism for the initiation step in cationic polymerization when methoxyethene reacts with BCI3 H₂O. Include unshared electrons and any nonzero formal charges. You do not need to show additional resonance forms. TA i Draw the curved arrow mechanism for the initiation step of this polymerization reaction. □ AN :CI: ‒‒‒‒‒‒‒ i 12D : CI: :CI—B :CI: + I H C N O S F P Cl Brarrow_forward
- One common type of cation exchange resin is prepared by polymerization of a mixture containing styrene and 1,4-divinylbenzene . The polymer is then treated with concentrated sulfuric acid to sulfonate a majority of the aromatic rings in the polymer. Q.) Explain how this sulfonated polymer can act as a cation exchange resinarrow_forwardDraw the structure of the polymer that results from anionic polymerization of p-trichloromethylstyrene (CCl3C6H4CH =CH2) using ethylene oxide as the electrophile to terminate the chain.arrow_forward
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