BackShow 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.
(a) Predict the identity of the major stereoisomer
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?
Predict the major product of the following bromination reactions.
(b)
Predict the major product of the following bromination reactions.
(c)
For the following reaction, answer questions (a)–(d).
(b) Which is the weakest bond in molecule A?
For the following reaction, answer questions (a)–(d).
(d) Given your choice in (b), why is it the weakest bond?
A halogenation intended to make compound A formed B instead.
(a) Suggest a mechanism for the intended formation of A.
A halogenation intended to make compound A formed B instead.
(c) Given the two mechanisms you drew, why might B have formed selectively?
In the following reaction, which C―H bond would be most likely to react with a bromine radical?