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

Mechanism for free-radical chlorination of cyclobutane
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.


Mechanism for free-radical chlorination of cyclobutane
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Draw the important resonance forms of the following free radicals.
(a)

(b)

(c)

(d)

(e)

(f)

The triphenylmethyl cation is so stable that some of its salts can be stored for months. Explain why this cation is so stable.

triphenylmethyl cation
(a) Draw a reaction-energy diagram for the following reaction:

The activation energy is 4 kJ/mol (1 kcal/mol), and the overall for the reaction is -110 kJ/mol (-27 kcal/mol).
(b) Give the equation for the reverse reaction.
(c) What is the activation energy for the reverse reaction?
When dichloromethane is treated with strong NaOH , an intermediate is generated that reacts like a carbene. Draw the structure of this reactive intermediate, and propose a mechanism for its formation.
Question: (a) Write the propagation steps leading to the formation of dichloromethane (CH2Cl2).
(b) Explain why free-radical halogenation usually gives mixture of products.
(c) How could an industrial plant control the proportions of methane and chlorine to favor production of CCl4? To favor production of CH3Cl?
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