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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

Label each hydrogen atom in the following compound as primary (1o), secondary (2o), or tertiary (3o)

(a)

(b)

(c)

(d)

e)

(f)

When exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as unreacted methane.

(a) Explain how a mixture is formed from this stoichiometric mixture of reactants, and propose mechanisms for the formation of these compounds from chloromethane.

(b) How would you run this reaction to get a good conversion of methane toCH3Cl? Of methane to CCl4?

In the presence of a small amount of bromine, cyclohexene undergoes the following light-promoted reaction:

(a) Propose a mechanism for this reaction.

(b) Draw the structure of the rate-limiting transition state.

(c) Use Hammond鈥檚 postulate to predict which intermediate most closely resembles this transition state.

(d) Explain why cyclohexene reacts with bromine much faster than cyclohexane, which must be heated to react.

When a small piece of platinum is added to a mixture of ethene and hydrogen, the following reaction occurs:

Doubling the concentration of hydrogen has no effect on the reaction rate. Doubling the concentration of ethene also has no effect.

(a) What is the kinetic order of this reaction with respect to ethene? With respect to hydrogen? What is the overall order?

(b) Write the unusual rate equation for this reaction.

(c)Explain this strange rate equation, and suggest what one might do to accelerate the reaction.

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.
See all solutions

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