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Chapter 10: Q7P-a (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 aromatic radical. Thus, the reaction at the primary end (which is less hindered) is favoured.

Step by step solution

01

Bromination of Cyclic 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 aromatic radical. Thus, the reaction at the primary end (which is less hindered) is favoured.

02

Bromination of 5-methylcyclohept-1-ene

Bromination of 5-methylcyclohept-1-ene with NBS results in the formation of two products i.e. 3-bromo-5-methylcycloheptene and 3-bromo-6 methylcycloheptene.

The reaction is given below:

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Most popular questions from this chapter

Carboxylic acids (RCOOH; pKa=5) are approximately 1011 times more

acidic than alcohols (ROH;pKa=16). In other words, a carboxylate ion(RCO2-)

is more stable than an alkoxide ion (RO-). Explain, using

resonance.

How would you prepare the following alkyl halides from the corresponding alcohols?

Which of the following compounds have the same oxidation level, and which have different levels?

How might you use a Suzuki–Miyaura reaction to prepare the biarylcompounds below? In each case, show the two potential reactionpartners.

In light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a carbocation plus halide ion (see Problem 10-45), propose a mechanism for the following reaction.
See all solutions

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