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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

Question: How might you replace a halogen substituent by a deuterium atom if you wanted to prepare a deuterated compound?

Predict the product and provide the entire catalytic cycle for theSuzuki鈥揗iyaura reactions below.

Question: Name the following alkyl halides:

Draw and name all of the monochlorination products that you might obtain from the radical chlorination of the compounds below. Which of the products is chiral? Are any of the products optically active?

(a) 2-methylbutane

(b) Methylcyclopropane

(c) 2,2-dimethylpentane

Draw the electron-pushing mechanism for the propagation steps of the allylic bromination reactions below. You may omit NBS in your mechanism, and use Br鈭� and Br2.

(b)
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