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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 16c
Chapter 10, Problem 16c

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
(c) Chemical structure comparison: two molecules with arrows indicating bonds, one with a tin (Sn) atom, assessing bond-dissociation energy.

Verified step by step guidance
1
Understand the concept of bond-dissociation energy: It is the energy required to break a bond in a molecule, resulting in the formation of radicals. The stability of the resulting radicals plays a crucial role in determining the bond-dissociation energy.
Identify the types of radicals formed: When a bond is broken, two radicals are formed. The stability of these radicals can be influenced by factors such as resonance, hyperconjugation, and the presence of electron-withdrawing or electron-donating groups.
Compare the stability of the radicals: More stable radicals result in lower bond-dissociation energy because less energy is required to form them. Conversely, less stable radicals result in higher bond-dissociation energy.
Evaluate the factors affecting radical stability: Consider the electronic effects such as resonance stabilization, hyperconjugation, and inductive effects. Radicals that are stabilized by resonance or hyperconjugation will generally have lower bond-dissociation energies.
Predict the bond with higher bond-dissociation energy: Based on the stability analysis, the bond that forms less stable radicals upon dissociation will have a higher bond-dissociation energy. This is because more energy is required to break the bond and form less stable radicals.

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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; higher bond-dissociation energy indicates a stronger bond. Understanding this concept helps predict which bonds are more stable and resistant to breaking.
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Radical Stability

Radical stability refers to the ability of a radical to exist without undergoing further reactions. Stability is influenced by factors such as resonance, hyperconjugation, and the electronegativity of atoms involved. More stable radicals are typically formed from bonds with lower bond-dissociation energies.
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Resonance and Hyperconjugation

Resonance and hyperconjugation are phenomena that stabilize radicals. Resonance involves the delocalization of electrons across adjacent atoms, while hyperconjugation involves the interaction of sigma bonds with adjacent pi systems or empty orbitals. These effects increase radical stability, influencing bond-dissociation energy predictions.
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Related Practice
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

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.

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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

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

(a)

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Textbook Question

A radical reaction, as it progressed through its propagation steps, involved the following radical species. Suggest which products might form in all possible termination steps (six products are possible).

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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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