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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

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

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.

(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.)

Question: Draw another resonance form for each of the substituted allylic cations shown in the preceding figure, showing how the positive charge is shared by another carbon atom. In each case, state whether your second resonance form is a more important or less important resonance contributor than the first structure. (Which structure places the positive charge on the more-substituted carbon atom?)

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

a)

b)

c)

d)

e)

f)
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