Predict the major, organic product of the following reaction.

The benzene ring alters the reactivity of a neighboring group in the benzylic position much as a double bond alters the reactivity of groups in the allylic position.

Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates.

b. Toluene reacts with bromine in the presence of light to give benzyl bromide. Propose a mechanism for this reaction.

Show how the following compounds could be prepared from 2-methylpropane:

a. 2-bromo-2-methylpropane 

Draw the products of the following reactions, including all stereoisomers:

d.

When a student attempted a bromination to produce compound A, they generated compound B instead. Rationalize the formation of B using the arrow-pushing formalism.

Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield.

a. How do you account for this difference?

b. What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis of chlorocyclohexane?

How could an industrial plant control the proportions of methane and chlorine to favor production of CCl₄? To favor production of CH₃Cl?

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).