Answered: Propose mechanisms for the formation…

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Propose mechanisms for the formation and reactions of ethers and epoxides.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.21P: Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for...

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Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

Propose mechanisms for the formation and reactions of ethers and epoxides.

Definition Definition Special class of cyclic ethers (R-O-R') with a three-atom ring. Epoxides are an important functional group in organic chemistry as they generate reactive centers due to their unusual high reactivity. This high reactivity make epoxides toxic and mutagenic.

Expert Solution

Step 1

Ethers can be prepared by the reaction of alcohol with alkyl halide in the presence of Na. This is known as Williamson Ether synthesis. The mechanism of the reaction is as follows:

Ether undergoes various reactions like chlorination to form chloro substituted derivative, oxidation to form peroxides, S_N2 reaction to form alcohol and alkyl halide etc.

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