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Chapter 4: Q 44P (page 234)

Write a mechanism for light-initiated reaction of cyclobutene with chlorine to give chlorocyclobutane. Label the initiation and propagation steps.

Short Answer

Expert verified

Mechanism for free-radical chlorination of cyclobutane

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

Mechanism

The mechanism consists of three parts which are initiation step, propagation step I and propagation step II.

Mechanism for free-radical chlorination of cyclobutane

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Most popular questions from this chapter

Question: Under base-catalyzed conditions, two molecules of acetone can condense to form diacetone alcohol. At room temperature250c, aboutof 5%the acetone is converted to diacetone alcohol. Determine the value of∆G0for this reaction.

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’s 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.

Write an equation for the reaction of vitamin E with an oxidizing radical (RO·) to give ROH and a less reactive free radical.

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)

Peroxides are often added to free-radical reactions as initiators because the oxygen-oxygen bond cleaves homolytically rather easily. For example, the bond-dissociation enthalpy of O-Obond in hydrogen peroxide (H-O-O-H)is only 213 kJ/mol (51 kcal/mol). Give a mechanism for the hydrogen peroxide- initiated reaction of cyclopentane with chlorine. The BDE for HO-Clis 210 kJ/mol (50kcal/mol).
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