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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

In Solved Problem 15-2, we simply predicted that the products would have a 1, 2-or 1, 4-relationship of the proper substitutents. Draw the charge-separated resonance forms of the reactants to support these predictions.

In a strongly acidic solution, cyclohexa-1, 4-diene tautomerizes to cyclohexa-1, 3-diene. Propose a mechanism for this rearrangement, and explain why it is energetically favorable.

Predict the major product for each proposed Diels-Alder reaction. Include stereochemistry where appropriate.

a)

b)

c)

Question: When is added to buta-1,3- diene at -150C, the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at 600C, the product ratio is 10% A and 90% B.

a. Propose structures for products A and B (Hint: In many case, an allylic carbocation is more stable than a bromonium ion.)

b. Propose a mechanism to account for formation of both A and B.

c. Show why A predominates at -150C and B predominates at 600C .

d. If you had a solution of pure A, and its temperature were raised to 600C , what would you expect to happen ? Propose a mechanism to support your prediction.

(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.)
See all solutions

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