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Chapter 6: Q57P (page 331)

Question: Propose mechanisms to account for the observed products in the following reactions.

Short Answer

Expert verified

a)

b)

Step by step solution

01

Allylic substitution 

In allylic bromination, the Br atom appears on the carbon next to the double bond which proceeds via a radical mechanism. The allylic radicals are very stable because of resonance-stabilization.

02

Proposing the mechanism 

Here, NBS will create a radical on the allylic position of the double bond and one more isomer will be formed by the rearrangement of the radical formed. The Br will be attached to

the radical position and will lead to the final product formation. Below are the mechanisms proposed for the given two parts:

(a)


Mechanism for reaction (a)

(b)


Mechanism for reaction (b)

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Most popular questions from this chapter

Question: Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

d)

Propose a mechanism involving a hydride shift or alkyl shift for each solvolysis reaction. Explain howeach rearrangement forms a more stable intermediate.

(a)

(b)

(c)

(d)

Question: Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

b)

Propose an SN1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.

Strawberry growers have used large quantities of methyl bromide (b.p. 4°C) to sterilize the soil before planting their crops. Like some of the freons, methyl bromide can diffuse up into the stratosphere, where it damages the protective ozone layer. Agricultural chemists have suggested using methyl iodide (b.p. 43°C) as a replacement for methyl bromide. Why is methyl iodide likely to be more toxic to agricultural pests (and people) than methyl bromide? Why is methyl iodide less likely to reach the stratosphere than methyl bromide?
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