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Exam 11: Radical Reactions

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Question 21

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Which of the following are possible termination steps in the chlorination of methane?

A)
B)
C)
D)

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Question 22

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Upon treatment with NBS and irradiation with UV light, 2-propyl-1-pentene produces exactly four monobrominated compounds (including stereoisomers). Draw and name the products of this reaction.

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Question 23

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Compound A, C₆H₁₂ reacts with HBr/ROOR to give compound B, C₆H₁₃Br. Compound C, C₆H₁₄, reacts with bromine and light to produce compound B, C₆H₁₃Br. Suggest structures for compounds A, B, and C.

Which monomer is used for the synthesis of Teflon?

Predict the major product of the following reaction:

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

Your textbook mentions that the free radical polymerization of ethylene can produce branches. Although branches of various lengths are possible, butyl branches are very common. Suggest an explanation for this fact.

Propose an efficient sequence of reactions to accomplish the following transformation.

Which intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide and hydrogen peroxide?

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 intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide?

Predict the major product(s) of the following reaction.

Which of the following is an example of initiation?

Use correct arrow formalism to show a homolytic bond cleavage of ethane to produce two methyl radicals.

Predict the major product(s) of the reaction shown below:

Methylenecyclopentane (below) 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?

A bromine radical can add to the $\pi$ bond of 2-methylpropene. Use correct arrow formalism to show this process and the expected result.

Use correct arrow formalism to show the second propagation step for the reaction of a chlorine radical with ozone.

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

Which of the following is (are) the likely major product(s) of the reaction shown?