Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 14.6, Problem 12P
Interpretation Introduction
Interpretation:
The mechanism of the acid catalyzed
Concept introduction:
Just like
To propose:
The mechanism of the acid catalyzed polymerization of 1, 3-butadiene.
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Chapter 14 Solutions
Organic Chemistry
Ch. 14.1 - Prob. 1PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.2 - Prob. 3PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.3 - Prob. 5PCh. 14.3 - Prob. 6PCh. 14.5 - Predict the product of the following Diels–Alder...Ch. 14.5 - Prob. 8PCh. 14.5 - Which of the following dienes have an s-cis...Ch. 14.5 - Predict the product of the following Diels–Alder...
Ch. 14.6 - Prob. 11PCh. 14.6 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Prob. 14PCh. 14.8 - Which of the following compounds would you expect...Ch. 14.SE - Prob. 16VCCh. 14.SE - Show the product of the Diels–Alder reaction of...Ch. 14.SE - Prob. 18VCCh. 14.SE - Prob. 19VCCh. 14.SE - Prob. 20MPCh. 14.SE - Prob. 21MPCh. 14.SE - In light of your answer to Problem 14-21 propose...Ch. 14.SE - Luminol, which is used by forensic scientists to...Ch. 14.SE - Prob. 24MPCh. 14.SE - Give IUPAC names for the following compounds:Ch. 14.SE - Prob. 26APCh. 14.SE - Prob. 27APCh. 14.SE - Electrophilic addition of Br2 to isoprene...Ch. 14.SE - Prob. 29APCh. 14.SE - Prob. 30APCh. 14.SE - Predict the products of the following...Ch. 14.SE - 2,3-Di-tert-butyl-1,3-butadiene does not undergo...Ch. 14.SE - Prob. 33APCh. 14.SE - Prob. 34APCh. 14.SE - Prob. 35APCh. 14.SE - Prob. 36APCh. 14.SE - Rank the following dienophiles in order of their...Ch. 14.SE - Prob. 38APCh. 14.SE - Prob. 39APCh. 14.SE - Prob. 40APCh. 14.SE - Although the Diels–Alder reaction generally...Ch. 14.SE - Prob. 42APCh. 14.SE - Tires whose sidewalls are made of natural rubber...Ch. 14.SE - Prob. 44APCh. 14.SE - Prob. 45APCh. 14.SE - Prob. 46APCh. 14.SE - Would you expect allene, H2C = C = CH2, to show a...Ch. 14.SE - The following ultraviolet absorption maxima have...Ch. 14.SE - Prob. 49APCh. 14.SE - -Ocimene is a pleasant-smelling hydrocarbon found...Ch. 14.SE - Draw the resonance forms that result when the...Ch. 14.SE - Prob. 52APCh. 14.SE - Treatment of 3,4-dibromohexane with strong base...Ch. 14.SE - Prob. 54APCh. 14.SE - Prob. 55APCh. 14.SE - Prob. 56APCh. 14.SE - Prob. 57APCh. 14.SE - Prob. 58APCh. 14.SE - Hydrocarbon A, C10H14, has a UV absorption at...Ch. 14.SE - Prob. 60APCh. 14.SE - Prob. 61APCh. 14.SE - Prob. 62APCh. 14.SE - Prob. 63APCh. 14.SE - Prob. 64APCh. 14.SE - The double bond of an enamine (alkene + amine) is...Ch. 14.SE - Prob. 66AP
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Similar questions
- 2. In free radical polymerization, the polymerization of CH,CH-CHOCOCH(allyl acetate) is very slow whereas that of CH, =CH-CD,OCOCH, is fast. Explain the reason,arrow_forwardExplain why a random copolymer is obtained when 3,3-dimethyl-1-butene undergoes cationic polymerization.arrow_forwardWhat is the basic mechanism of an Anionic polymer (acrylic acid based as carbomers) in regards to function and “activation”? How do they work and thicken?arrow_forward
- Macromolecules can also be formed from cyclic monomers such as cyclic hydrocarbons, ethers, esters, amides, siloxanes, and sulfur (eight-membered ring). Thus, ring-opening polymerization is of particular interest, since macromolecules of almost any chemical structure can be prepared. Choose two of the above type polymers to explain the mechanism and chemical reaction of polymerization process.arrow_forwardShow the chain reaction (initiation ,propagation and termination) step in a polymer known as PMMA .arrow_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
- Use mechanisms to show how monomers polymerize under acidic, basic, orfree-radical conditions. For chain-growth polymerization, determine whether the reactive end is more stable as a cation (acidic conditions), anion (basic conditions), or free radical (radical initiator). For step-growth polymerization, consider the mechanism of the condensation.arrow_forwardWhich of the following is the first step in the cationic polymerization of alkenes? Select one: Attack of π-electrons to a proton H+. Reduction of the π-electrons. Elongation of the polymer chain. Attack of π-electrons to a carbocation. Which of the following is FALSE regarding terminal alkynes? Select one: O The proton in the terminal carbon is weakly acidic. They react with H₂O, H₂SO4, HgSO4 to produce an aldehyde. O The hydrohalogenation reaction yields a geminal dihalide. O Treatment with alcoholic AgNO3 produces a silver acetylide.arrow_forwardExplain why acrylonitrile (CH2 = CHCN) undergoes cationic polymerization more slowly than but-3-enenitrile (CH2 = CHCH2CN).arrow_forward
- Draw the structure of the polymer that results from anionic polymerization of p-trichloromethylstyrene (CCl,CgH,CH=CH2) using ethylene oxide as the electrophile to terminate the chain.arrow_forwardExplain why styrene (CH2=CHPh) can be polymerized to polystyrene by all three methods of chain-growth polymerization.arrow_forwardStyrene 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 autoinitiated polymerization?arrow_forward
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