Suggest reagents and reaction conditions that would result in synthesis of the following bromoalkanes.
(c)

A halogenation intended to make compound A formed B instead.

(d) Without looking it up, would you expect C–H_a or C–H_b to have the lower bond-dissociation energy?

In the second propagation step in the bromination of toluene, Br₂ is only attacked by a radical on the substituent carbon. Why?

For each compound, predict the major product of free-radical bromination. Remember that bromination is highly selective, and only the most stable radical will be formed.

(e)

(c) Based on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator.

(d) Propose a mechanism for this reaction.

Predict the product of the following benzylic bromination reactions.

(c)

What is the major product of the following reactions? Disregard stereoisomers:

c.

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.

Show the products you expect when each compound reacts with NBS with light shining on the reaction.

(d)