Write the propagation steps leading to the formation of dichloromethane (CH₂Cl₂) from chloromethane.

Using the BDEs in Table 4-2 (page 167), 

(c) Suggest two reasons why iodine does not react well with methane.

Alkoxy radicals (R—O•) are generally more stable than alkyl (R•) radicals. Write an equation showing an alkyl free radical (from burning gasoline) abstracting a ­hydrogen atom from tert-butyl alcohol, (CH₃)₃COH. Explain why tert-butyl alcohol works as an antiknock additive for gasoline

Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

(a)

When exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a ­chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as ­unreacted methane.

b. How would you run this reaction to get a good conversion of methane to CH₃Cl? Of methane to CCl₄?

Each of the following proposed mechanisms for the free-radical chlorination of methane is wrong. Explain how the experimental evidence disproves each mechanism.

b.

b. Calculate ΔH° for each step in this reaction.

c. Calculate the overall value of ΔH° for this reaction.

For each alkane,

1. draw all the possible monochlorinated derivatives.

a. Cyclopentane

b. Methylcyclopentane

For each alkane,

2. determine whether free-radical chlorination would be a good way to make any of these monochlorinated derivatives. Will the reaction give mostly one major product?

a. Cyclopentane

b. Methylcyclopentane