11. Radical Reactions

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.

f.

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

c. HBr + peroxide 

d. HCl + peroxide

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iii) HBr, H₂O₂

(b)

Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]

(d)

What reagents are needed to carry out the following syntheses?

Show how hex-1-yne might be converted to

a. 1,2-dichlorohex-1-ene.

b. 1-bromohex-1-ene.

c. 2-bromohex-1-ene.

Propose a mechanism for the following reaction: