The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:

b. The bromination of cyclohexene using NBS gives only one major product, as shown on the previous page. Explain why there is no second product from an allylic shift.

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

c. 1-bromobutane and 1-chlorobutane

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

b. isopropyl chloride and tert-butyl bromide

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.

(d)

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.

(c)

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

The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:

a. Give a mechanism for this reaction, showing how the two products arise as a ­consequence of the resonance-stabilized intermediate.