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Ch.4 - The Study of Chemical Reactions
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.4 - The Study of Chemical ReactionsProblem 45b
Chapter 4, Problem 45b

Draw the important resonance forms of the following free radicals.
b.

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1
Identify the free radical in the given structure. In this case, the free radical is located on the CH2 group attached to the benzene ring.
Recognize that the benzene ring can participate in resonance with the free radical. The unpaired electron on the CH2 group can interact with the π-electrons of the benzene ring.
Draw the first resonance form by moving the unpaired electron from the CH2 group to form a double bond with the adjacent carbon of the benzene ring. This will result in the movement of the π-electrons in the benzene ring.
Continue the resonance by moving the π-electrons around the benzene ring. This will create a new resonance form where the unpaired electron is now located on a different carbon atom in the benzene ring.
Repeat the process to generate additional resonance forms, ensuring that the unpaired electron is delocalized around the benzene ring, which stabilizes the free radical through resonance.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In the case of free radicals, resonance can help distribute the unpaired electron across multiple atoms, stabilizing the radical. Understanding how to draw these structures is crucial for predicting the reactivity and stability of the molecule.
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Free Radicals

Free radicals are species that contain an unpaired electron, making them highly reactive. They can be formed through various processes, including the homolytic cleavage of covalent bonds. In organic chemistry, understanding the behavior of free radicals is essential for predicting reaction mechanisms and outcomes, especially in radical substitution reactions.
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Aromatic Stability

Aromatic compounds, like benzene, exhibit unique stability due to their cyclic structure and delocalized π electrons. This stability influences the behavior of substituents, including free radicals, on the aromatic ring. Recognizing how resonance and aromaticity contribute to the stability of radicals is key to understanding their reactivity in organic reactions.
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Related Practice
Textbook Question

In the presence of a small amount of bromine, the following light-promoted reaction has been observed.

a. Write a mechanism for this reaction. Your mechanism should explain how both products are formed. (Hint: Notice which H atom has been lost in both products.)

Textbook Question

Draw the important resonance forms of the following free radicals.

a.

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Textbook Question

In the presence of a small amount of bromine, the following light-promoted reaction has been observed.

b. Explain why only this one type of hydrogen atom has been replaced, in preference to any of the other hydrogen atoms in the starting material.

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Textbook Question

For each alkane,

1. draw all the possible monochlorinated derivatives.

c. 2-methylpentane

d. 2,2,3,3-tetramethyl butane

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Textbook Question

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

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Textbook Question

Draw the important resonance forms of the following free radicals.

(c)

(d)

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