A. Which ether is most apt to form a peroxide? b. Which...

Key Concepts

Radical Stability

The tendency to form peroxides in ethers is significantly influenced by how well the resulting radical intermediate is stabilized. Structural features that stabilize the radical via resonance or hyperconjugation will enhance the likelihood of peroxide formation. Ethers with more stabilized radicals display a higher propensity for this process.

Steric Hindrance and Structural Constraints

Ethers with significant steric hindrance around the reactive ??positions, or those in which ??hydrogens are absent, are less apt to form peroxides. Their molecular structure does not favor the necessary hydrogen abstraction or subsequent radical stabilization, thus reducing the risk of peroxide formation.

Autoxidation

Autoxidation is a common reaction of organic compounds with molecular oxygen in which radicals are formed and propagate a chain reaction, leading to the formation of peroxides. In ethers, this process typically involves hydrogen abstraction adjacent to the oxygen atom, generating radical intermediates that can react further with oxygen to form hydroperoxides.

Alpha?Hydrogen Abstraction

The presence and accessibility of hydrogens on the carbon atoms adjacent to the ether oxygen (??hydrogens) is crucial in peroxide formation. Ethers that possess easily abstractable ??hydrogens are more prone to initiate the radical reaction that leads to peroxide formation, whereas ethers lacking these hydrogens are much less susceptible to this transformation.

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