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Chapter 10: Q7P-b (page 297)

What products would you expect from reaction of the following alkenes with NBS? If more than one product is formed, show the structures of all.

Short Answer

Expert verified

In this reaction, the two product formed are not in equal proportions. The reaction at the two ends is not equal because of the formation of a unsymmetrical allylic radical. Thus, the reaction at the primary end (which is less hindered) is favoured.

Step by step solution

01

Bromination of allylic alkenes

In this reaction, the two product formed are not in equal proportions. The reaction at the two ends is not equal because of the formation of a unsymmetrical allylic radical. Thus, the reaction at the primary end (which is less hindered) is favoured.

02

Bromination of 2-methylhex-3-ene

Bromination of 2-methylhex-3-ene with NBS results in the formation of four different bromohexenes and two different allylic radicals.

The reaction is given below:

Product formation between given alkene and NBS

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Most popular questions from this chapter

Sort the radicals below from most stable to least stable.




Question: The syntheses shown here are unlikely to occur as written. What is

wrong with each?




Reaction 1

Reaction 2

How would you prepare the following compounds, starting with cyclopentene and any other reagents needed? (c) 3-Bromocyclopentene.

Draw and name all monochloro products you would expect to obtain from radical chlorination of 2-methylpentane. Which, if any, are chiral?

Alkylbenzenes such as toluene (methylbenzene) react with NBS to give

products in which bromine substitution has occurred next to the aromatic ring (the benzylic position). Explain, based on the bond dissociation energies in Table 6-3 on page 170.
See all solutions

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