The chlorination of pentane gives a mixture of three monochlorinated products.
b. Predict the ratios in which these monochlorination products will be formed, remembering that a chlorine atom abstracts a secondary hydrogen about 4.5 times as fast as it abstracts a primary hydrogen.

The chlorination of pentane gives a mixture of three monochlorinated products.

a. Draw their structures.

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.

a. Explain how a mixture is formed from this stoichiometric mixture of reactants, and propose mechanisms for the ­formation of these compounds from chloromethane.

a. Draw the structure of the transition state for the second propagation step in the chlorination of methane.

Show whether the transition state is product-like or reactant-like and which of the two partial bonds is stronger.

Peroxides are often added to free-radical reactions as initiators because the oxygen–oxygen bond cleaves homolytically rather easily. For example, the bond-dissociation enthalpy of the O―O bond in hydrogen peroxide (H―O―O―H) is only 213 kJ/mol (51 kcal/mol). Give a mechanism for the hydrogen peroxide-initiated reaction of cyclopentane with chlorine. The BDE for HO―Cl is 210 kJ/mol (50 kcal/mol).

When dichloromethane is treated with strong NaOH, an intermediate is generated that reacts like a carbene. Draw the structure of this reactive intermediate, and propose a mechanism for its formation.

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?