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.

Short Answer

Expert verified

Answer

b. The mechanism for the formation of three products:


Step by step solution

01

Radical reactions

Radical reactions involve three steps—initiation (generation of free radical), propagation (free radical combines with hydrogen), and termination (two radicals react in such a way that the chain no longer propagates).In the last step, we get the products.

02

Mechanism for the formation of three products

(b)In the first step, when NBS reacts with HBr, it generates a low concentration of Br2.

Generation of low concentration of bromine radicals

Then the initiation step follows, where the two bromine radicals are formed.

Initiation step

In the propagation step, abstraction of hydrogen takes place and generates allylic radical. The radical will be a mixture of cis and trans.

The mechanism for the formation of three products

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Most popular questions from this chapter

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.

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.

Question: When Br2 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 to600C , what would you expect to happen ? Propose a mechanism to support your prediction.

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.)

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