When (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane is halogenated, one stereoisomer is produced in excess.
(a) Predict the identity of the major stereoisomer

The radical fluorination of 2-methyl propane resulted in a 14:86 ratio of products.

(b) From the relative reactivity, calculate the difference in energy between the transition states of the first propagation steps leading to a 1° and 3° radical.

Show how free-radical halogenation might be used to synthesize the following ­compounds. In each case, explain why we expect to get a single major product.

(a) 1-chloro-2,2-dimethylpropane (neopentyl chloride)

(b) 2-bromo-2-methylbutane

Rationalize the fact that reaction A results in an unequal mixture of products, but reaction B yields an equal mixture of two products.

Because of the angle strain present in cyclopropanes, they tend to open up in the presence of nearby radicals. Show a mechanism for the following reaction that demonstrates this principle.

When (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane is halogenated, one stereoisomer is produced in excess.

(b) explain why this reaction did not produce an equal mixture of stereoisomers.

Predict the major products of the following alkane halogenation reactions. [The number of products shown ignores the formation of racemic mixtures.]

(b)

Predict the major products of the following alkane halogenation reactions. [The number of products shown ignores the formation of racemic mixtures.]

(d)

Can you make a 1° bromoalkane like (3-bromopropyl)cyclopentane using alkane halogenation? Why or why not?