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Chapter 15: Q9P (page 765)

When methylenecyclohexane is treated with a low concentration of bromine under irradiation by a sunlamp, two substitution products are formed.

  1. Propose structures for these two products.
  2. Propose a mechanism to account for their formation.

Short Answer

Expert verified

a)

b)

Step by step solution

01

Bromination

A bromination reaction in the presence of light is a type of photochemical reaction. A free radical forms during the reaction, which attacks a nucleophile.There is the formation of substitution products along with HBr.

02

Structure of the two products

  1. When methylenecyclohexane is treated with a low concentration of bromine under irradiation by a sunlamp, the two substitution products formed are as follows:

Two substitution products

03

Mechanism of the formation

  1. In the first step, the cleavage of Br2in the presence of a sunlamp takes place: two bromine radicals form, and one bromine radical attacks the methylenecyclohexane and forms two allylic carbocations. Further, on reaction with Br2, the two substitution products are formed.

Mechanism of the reaction

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Most popular questions from this chapter

Predict the products of the following Diels-Alder reactions.

a)

b)

c)

d)

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

a)

b)

c)

d)

e)

f)

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: 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?)

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.
See all solutions

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