Exam 11: Radical Reactions

Free radical chlorination of ethane can produce higher halogenation products (dichlorinated,trichlorinated,etc…)in addition to chloroethane.How could the production of higher halogenated products be minimized?

Use correct arrow formalism to show the following radical process:

Which term best describes the process shown below?

Compound A has molecular formula C₉H₂₀.Compound A produces three constitutional isomers upon chlorination,and one constitutional isomer upon bromination.Which of the following are possible structures of Compound A?

Thermal cracking of butane can produce ethyl radicals via homolytic cleavage.Use correct arrow formalism to show this process.

Which monomer is used for the synthesis of Teflon?

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

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

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

What term most accurately describes the process shown below?

Azobisisobutyronitrile (AIBN)is commonly used as a radical initiator.Use correct arrow formalism to show this process.

Which of the following processes is responsible for the fact that free radical bromination of methane is slower than free radical chlorination?

Use correct arrow formalism to show the following radical process:

Use correct arrow formalism to show the propagation steps in the chlorination of propane to produce 2-chloropropane.

One possible product of thermal cracking of hexane is 1-butene.Use correct arrow formalism to suggest a possible mechanism for this process starting from an alkyl radical.

Upon treatment with NBS and irradiation with UV light,1-ethyl-4-methyl produces three monobrominated compounds (including stereoisomers).Draw the products of this reaction.

The free radical polymerization of styrene with benzoyl peroxide yields a polymer that has repeat units arranged primarily in a 'head-to-tail' arrangement.This means that the phenyl group primarily ends up placed at alternating carbon atoms along the chain.Use correct arrow formalism to show why this arrangement is preferred over a 'head-to-head' or 'tail-to-tail' arrangement.

Which term best describes the process shown below?

How many constitutional isomers are possible if propane is dichlorinated? Draw them.

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