Exam 10: Radical Reactions

Of the four choices shown, which is likely to be a major product of the reaction below?

When 1,1,4-trimethylcyclohexane is exposed to Br₂ and UV light, only one major product is obtained. How many distinct resonances in the proton-decoupled ¹³C NMR spectrum are observed in the product?

Which of the following are the products of a homolytic cleavage of a C-C bond of ethane?

Propose a synthesis of 4-penten-2-ol from propene.

Propose a sequence of reactions to accomplish the following synthesis.

Give the arrows to show the second propagation step for the reaction of a chlorine radical with ozone.

Which of the following shows the correct products initially formed when ozone absorbs ultraviolet light?

Which monomer is used for the synthesis of Teflon?

Give the arrows to show the mechanism of the following radical process.

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

Which of the following is the repeat unit for the polymer produced in the following reaction?

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.

Polychloroprene (Neoprene) can be prepared by the free-radical polymerization of chloroprene. Give the arrows to show the propagation steps that lead to the isomer of polychloroprene shown below.

Rank the following radicals in order of decreasing stability (most stable to least stable).

Propose a sequence of reactions to accomplish the following synthesis.

Both compounds A and B have molecular formula C₆H₁₄. Monochlorination of compound A results in the formation of two constitutional isomers. Monochlorination of compound B results in the formation of four constitutional isomers. Identify compounds A and B, and show the products of each monochlorination.

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

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

Which of the following represents a propagation step in the monochlorination of methylene chloride (CH₂Cl₂)?

Propose a synthesis of 2-butyn-1-ol from propane.