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Chapter 15: Q64. (page 570)

Question. Ethers are oxidized with to form hydroperoxides that decompose violently when heated. Draw a stepwise mechanism for this reaction.

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01

Free radical formation

The breaking of chemical bonds generates free radicals to generate radicals with one or more unpaired electrons in their outermost shells.

The oxygen molecule would break a C-H bond in tetrahydrofuran (THF), generating a free radical. The radical reacts with another molecule of oxygen to form a C-O-O linkage.

Free radical reaction initiated by oxygen molecule

02

Reaction with another THF

This molecule is further treated with another molecule of tetrahydrofuran to form the unstable hydroperoxide.

Formation of the unstable hydroperoxide

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