Iodination of alkanes using iodine (I2) is usually an unfavorable reaction. (See Problem...

Iodination of alkanes using iodine (I₂) is usually an unfavorable reaction. (See Problem 4-17, for example.) Tetraiodomethane (CI₄) can be used as the iodine source for iodination, in the presence of a free-radical initiator such as hydrogen peroxide. Propose a mechanism (involving mildly exothermic propagation steps) for the following proposed reaction. Calculate the value of for each of the steps in your proposed mechanism.

The following bond-dissociation energies may be helpful:

(a) Using the BDEs in Table 4-2 (p. 143), compute the value of ΔH° for each step in the iodination of methane.

Reference: Problem 4-17:

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