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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

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.

Question: Draw Lewis structures for the following free radicals.

(a)The ethyl radical, CH3-CH2

(b)The tert butyl radical, (CH3 )3C

(c)The isopropyl radical,(2-propyl radical)

(d)The iodine atom

Use bond-dissociation enthalpies (Table 4-2, p.203) to calculate values of螖Hfor the following reactions.

(a)

(b)

(c)

(d)

(e)

(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?

(a) Draw the structure of the transition state for the second propagation step in the chlorination of methane.

Show whether the transition state is product-like or reactant-like and which of the two partial bonds is stronger.

(b) Repeat for the second propagation step in the bromination of methane.
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