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Chapter 15: PROBLEM 15.11 (page 766)

Question: Predict the product(s) of light-initiated reaction with NBS in CCl4 for the following starting materials.

  1. cyclohexene
  2. 3,4-dimethylhex-3-ene

Short Answer

Expert verified

Answer

c.

Step by step solution

01

Bromination using NBS

For allylic bromination, a convenient bromine source is N-bromosuccinimide (NBS), a derivative of succinimide.

NBS is denser than carbon tetrachloride and is not very soluble in it.

02

Product from ethylbenzene

c. When ethylbenzene undergoes a light-initiated reaction with NBS in CCl4 , it forms the below product.

Ethylbenzene undergoes a light-initiated reaction with NBS inCCl4

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Most popular questions from this chapter

(a)Show that the [4+4] cycloaddition of two butadiene molecules to give cycloocta-1,5-diene is thermally forbidden but photochemically allowed.

(b)There is a different, thermally allowed cycloaddition of two butadiene molecules. Show this reaction, and explain why it is thermally allowed. (Hint: Consider the dimerization of cyclopentadiene.)

Phenolphthalein is an acid-base indicator that is colorless below pH 8 and red above pH 8. Explain briefly why the first structure is colorless and the second structure is colored.

Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.

a. 3-phenylprop-1-ene

b.5-methylhex-2-ene

c. dec-5-ene

Predict the products of the following proposed Diels-Alder reactions.

a)

b)

c)

d)

e)

f)

Question: When N-bromosuccinimide is added to hex-1-ene in CCl4and a sunlamp is shone on the mixture, three products result.

  1. Give the structures of these three products.
  2. Propose a mechanism that accounts for the formation of these three products.
See all solutions

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