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Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 18a
Chapter 10, Problem 18a

Using the bond-dissociation energies in Table 5.6,
(a) predict whether or not a fluorine radical would be selective for forming a single radical from propane.

Verified step by step guidance
1
Understand the concept of bond-dissociation energy: Bond-dissociation energy is the energy required to break a bond in a molecule, resulting in the formation of radicals. It is a measure of the bond strength.
Identify the relevant bond-dissociation energies: Look up the bond-dissociation energies for the C-H bonds in propane and the C-H bonds in the potential radical products. This will help determine which bond is most likely to be broken by the fluorine radical.
Consider the reactivity of fluorine radicals: Fluorine radicals are highly reactive due to their high electronegativity and small size. They tend to react quickly and may not be very selective in their reactions.
Compare the bond-dissociation energies: Analyze the bond-dissociation energies of the primary and secondary C-H bonds in propane. Typically, secondary C-H bonds have lower bond-dissociation energies compared to primary C-H bonds, making them more likely to be broken.
Predict the selectivity: Based on the bond-dissociation energies and the reactivity of fluorine radicals, predict whether the fluorine radical will preferentially form a single radical from propane or if it will react non-selectively with multiple C-H bonds.

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Key Concepts

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

Bond-Dissociation Energy

Bond-dissociation energy is the energy required to break a bond in a molecule, resulting in the formation of radicals. It is a measure of bond strength and varies depending on the atoms involved and the molecular environment. Understanding these energies helps predict the stability of radicals formed during chemical reactions.
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Radical Selectivity

Radical selectivity refers to the preference of a radical to react with certain types of bonds over others. This selectivity is influenced by factors such as bond-dissociation energies and steric effects. In the context of fluorine radicals, their high reactivity can lead to less selectivity, making it crucial to analyze bond energies to predict reaction outcomes.
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Propane Structure

Propane is a three-carbon alkane with the molecular formula C3H8. It consists of primary and secondary hydrogen atoms, which differ in their bond-dissociation energies. Understanding the structure of propane is essential for predicting which hydrogen atoms are more likely to be abstracted by a radical, influencing the formation of specific radicals.
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Related Practice
Textbook Question

Using the bond-dissociation energies in Table 5.6,

(a) predict whether or not an iodine radical would be selective for forming a single radical propane.

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Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(d)

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Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(c)

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Textbook Question

Using the bond-dissociation energies in Table 5.6,

(b) Will the transition state be reactant-like or product-like? Explain your answer.

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Textbook Question

When (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane is halogenated, one stereoisomer is produced in excess.

(a) Predict the identity of the major stereoisomer

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Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(b)

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