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Problem 24

Styrene undergoes anionic polymerization at a faster rate than \(p\) -methoxystyrene. Suggest an explanation for this observation.

Problem 25

Given that \(-\mathrm{C} \square \mathrm{N}\) stabilizes carbanions better than phenyl, which monomer would you start with to prepare a copolymer of styrene and acrylonitrile?

Problem 27

Linear low-density polyethylene is a copolymer in which ethylene is polymerized under Ziegler-Natta conditions in the presence of a smaller quantity of a second alkene such as 1 -hexene. What structural feature characterizes the resulting polymer?

Problem 28

(a) Bisphenol A (shown) is made by the reaction of phenol and acetone. Suggest a mechanism for this reaction. Assume acid \(\left(\mathrm{H}_{3} \mathrm{O}^{+}\right)\) catalysis. (b) Bisphenol B is made from phenol and 2-butanone. What is its structure?

Problem 29

Poly(ethylene oxide) can be prepared from ethylene oxide by either anionic or cationic polymerization methods. Write reaction mechanisms for both processes. Use \(\mathrm{H}_{3} \mathrm{O}^{+}\) as the acid and \(\mathrm{OH}^{-}\) as the base.

Problem 38

The polystyrene-supported quaternary ammonium chloride shown was treated with aqueous sodium hydroxide, then shaken with a solution of compound \(\mathrm{X}\) and phenol in toluene at \(90^{\circ} \mathrm{C}\) to give butyl phenyl ether in \(97 \%\) yield. What is compound \(\mathrm{X}\) ? A. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) C. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) B. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) D. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\)

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