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Exam 10: Radical Reactions

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Question 21

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Give arrows to show a homolytic bond cleavage of ethane to produce two methyl radicals.

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Question 22

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Give the arrows to show the propagation steps for the autooxidation of diethyl ether.

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Question 23

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Poly(methyl methacrylate) (PMMA) is a light, shatter-resistant plastic prepared by the free-radical polymerization of methyl methacrylate (shown below) . What is the repeat unit of PMMA?

Draw all of the reasonable resonance structures for the radical shown below.

Identify an example of initiation.

Which monomer is used for the synthesis of poly(vinyl chloride) ?

Draw the major product(s) of the following reaction. Is the product optically active? Explain.

Which term most accurately describes the process shown below?

Methylenecyclopentane can be exposed to allylic bromination conditions to give multiple regioisomeric compounds, including Compound X. Compound X can then be hydrogenated to give Compound Y, which has only 4 distinct resonances in the proton-decoupled ¹³C NMR spectrum. What are the structures of compounds X and Y?

Compound A has molecular formula C₉H₂₀. Compound A produces exactly three constitutional isomers upon monochlorination, and one major constitutional isomer upon monobromination. Which of the following are possible structures of compound A?

Which of the following shows the initiation step of monochlorination of methane?

Which of the following is the rate-determining step in the free-radical bromination of methane?

Propose a sequence of reactions to accomplish the following synthesis.

Cyclic compound A has molecular formula C₅H₁₀ and undergoes monochlorination to yield exactly three different constitutional isomers. Identify compound A and show the monochlorination products.

Upon treatment with NBS and irradiation with UV light, 2-methyl-2-butene reacts to produce exactly six monobrominated compounds. Draw the products of this reaction.

Predict the major product obtained upon radical bromination of t-butylcyclohexane.

Which of the following is most reactive towards chlorination?

Which of the labeled C-H bonds is the weakest?

Draw arrows to show termination by coupling of two growing poly(vinyl chloride) chains.

Which of the following would you expect to function as an initiator at the lowest temperature?