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Chapter 4: Q 47P (page 234)

For each compound, predict the major product of free-radical bromination. Remember that bromination is highly selective, and only the most stable radical will be formed.

(a) cyclohexane

(b) methylcyclopentane

(c) decalin

(d) hexane

(e)

(f)

Short Answer

Expert verified

a)

b)

c)

d)

e)

f)

Step by step solution

01

Free radicals

An atom or group of atoms containing odd or unpaired electron is known as the free radical. The unpaired electron is represented by a single unpaired dot in the formula. Free radicals are electrically neutral. They are highly reactive species formed by homolytic fission of a covalent bond.

02

Steps involved in free radical chain reaction

In a free-radical chain reaction, free radicals are generally created in the initiation steps. A free radical and a reactant is combined to yield a product and another free radical in the propagation steps. Lastly, the number of free radicals generally decrease in the termination steps.

03

Predicting the major product

Free-radical bromination is highly selective and only the most stable product will be formed.

(a)

Only one possible product is formed.

(b)

Tertiary radical is formed.

(c)

Tertiary radical is formed.

(d)

Secondary radical is formed.

(e)

Benzylic radical is formed.

(f)

Allylic radical is formed.

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Most popular questions from this chapter

Question: The reaction of tert-butyl chloride with methanol

Is found to follow the rate equation

(a) What is the kinetic order with respect to tert-butyl chloride?

(b)What is the kinetic order with respect to methanol?

(c)What is the kinetic order overall?

Question: The bromination of methane proceeds through the following steps:

(a) Draw a complete reaction-energy diagram for this reaction.

(b) Label the rate-limiting step.

(c) Draw the structure of each transition state

(d) Compute the overall value of鈭�H0for the bromination.

When healthy, Earth鈥檚 stratosphere contains a low concentration of ozone (O3)that absorbs potentially harmful ultraviolet (UV) radiation by the cycle shown at right.

Chlorofluorocarbon refrigerants, such as Freon 12 (CF2Cl2), are stable in the lower atmosphere, but in the stratosphere, they absorb high-energy UV radiation to generate chlorine radicals.

The presence of a small number of chlorine radicals appears to lower ozone concentrations dramatically. The following reactions are all known to be exothermic (except the one requiring light) and to have high-rate constants. Propose two mechanisms to explain how a small number of chlorine radicals can destroy large numbers of ozone molecules. Which of the two mechanisms is more likely when the concentration of chlorine atoms is very small?

The chlorination of pentane gives a mixture of three monochlorinated products.

(a) Draw their structures.

(b) Predict the ratios in which these monochlorination products will be formed, remembering that a chlorine atom abstracts a secondary hydrogen about 4.5 times as fast as it abstracts a primary hydrogen.

(a) Compute the heats of reaction for abstraction of a primary hydrogen and a secondary hydrogen from propane by a fluorine radical.

(b) How selective do you expect free-radical fluorination to be?

(c) What product distribution you expect to obtain from the free-radical fluorination of propane?
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