6. Nylon 6 is commercially produced via the hydrolytic polymerization of E-caprolactam(azepan-2-one). The mechanism can occur via chain-growth and step-growthmechanisms. Draw these two mechanisms and explain which is expected topredominate.

Answered: 6. Nylon 6 is commercially produced via…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter29: Organic Polymer Chemistry

Section: Chapter Questions

Problem 29.11P

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11. Draw the repeating segment for the polymer formed from the reactions using the given monomer(s). (a) H₂C=CH₂ (b) CICH₂CH₂OCH₂CH₂CI+ (c) O=C=N- TICI4 (CH3CH₂)2AICI (d) HO- CH3 CH3 N. H -N=C=O + HOCH₂CH₂OH OH + & amine
(1) Explain the following polymerization mechanism by showing propagation reactions with the catalyst three times (draw chemical structures of the intermediates of the first, second, and third reaction with the monomer and catalysts). LnW=CHR' tanda (2) Why is HT-3-hexyl polythiophene better in conductivity than other regioisomers? Explain the reasons from the intramolecular and intermolecular aspects, respectively.
Draw the brief arrow pushing mechanism of the formation of this polymer(synthesis of Nylon (6,6)
2)
Draw a structural formula of the polymer resulting from base-catalyzed polymerization of each compound. Would you expect the polymers to be optically active? (S)-(+)-lactide is the dilactone formed from two molecules of (S)-(+)-lactic acid.
An equimolar blend of 1,4-hydroquinone diallylether and ethylene glycol dimercaptoacetate containing a small amount of benzophenone (radical photoinitiator) is polymerized by irradiating the blend with ultraviolet (UV) light. (a) Write a balanced chemical equation for the polymerization. (b) How would you classify this polymerization according to the reaction mechanism? (c) Calculate the extent of reaction needed to produce a polymer with a number average molar mass of 20,000 g/mole (neglect the effect of end groups in the calculation). (d) Draw the structure of the polymer that is obtained when the mole ratio of diallyl ether to dithiol is 1.1. (e) Explain briefly the consequences of including a tetrafunctional thiol in the polymerization with the exact stoichiometry 2:1:4 of difunctional thiol to tetrafunctional thiol to difunctional allylic ether. HS HS 1,4-hydroquinone diallylether Ethylene glycol dimercaptoacetate
For the cationic polymerization of ethyl vinyl ether initiated with a water/aluminum chloride initiator system shown below, give the mechanisms and products for the following reactions. n H₂O AICI 3 a) initiation (include equilibrium for initiator creation), b) propagation, and c) termination by initiator recombination.
Predict the Product. Predict the major organic product(s) or reactant(s) for the following reactions. Please use proper polymer notation and show one (1) repeat unit for the products. (9 pts total) зов OH HO OH Polymerize Polymerize HINT: ring-opening Polymerize [स
Show by means of chemical equations the initiation, propagation, transfer and termination steps (if any) in the linear chain polymerizations a) – d) below. For each reaction, clearly show the initiating species, active center, repeating unit and end- groups of the polymer chains that are formed and comment on the mechanism involved: a) Styrene initiated with potassium amide in liquid ammonia as solvent. b) Isobutylene (2-methylpropene) initiated with boron trichloride/tert-butyl chloride as catalyst in methyl chloride as solvent. c) 1,3-Butadiene initiated with n-buytylithium (CAH9LI) in tetrahydrofuran (THF) at 30°C and quenched with ethylene oxide followed by acidification. d) Propylene oxide initiated with potassium methoxide in methanol as solvent.
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Radical polymerization of styrene gives a linear polymer. Radical polymerization of a mixture of styrene and 1,4-divinylbenzene gives a cross-linked network polymer of the type shown in Figure 29.1. Show by drawing structural formulas how incorporation of a few percent of 1,4-divinylbenzene in the polymerization mixture gives a cross-linked polymer.
None

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6. Nylon 6 is commercially produced via the hydrolytic polymerization of E-caprolactam (azepan-2-one). The mechanism can occur via chain-growth and step-growth mechanisms. Draw these two mechanisms and explain which is expected to predominate.