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10 MECHANISMS

Ethers, Epoxides & Sulfur

Acid-Catalyzed Ether Synthesis

Acid-Catalyzed Ether Synthesis

Two alcohols condense to a symmetrical ether.

Williamson Ether Synthesis

Williamson Ether Synthesis

An alkoxide does SN2 on an alkyl halide.

Acidic Ether Cleavage

Acidic Ether Cleavage

HX cleaves an ether into two fragments.

Ether Autooxidation

Ether Autooxidation

Ethers form explosive peroxides on standing in air.

Alkene Epoxidation

Alkene Epoxidation

A peroxyacid delivers an oxygen to make an epoxide.

Bromohydrin to Epoxide

Bromohydrin to Epoxide

Base closes a halohydrin into an epoxide.

Epoxide Opening (Base)

Epoxide Opening (Base)

Nucleophile attacks the less hindered carbon.

Epoxide Opening (Acid)

Epoxide Opening (Acid)

Nucleophile attacks the more substituted carbon.

Thiol Alkylation

Thiol Alkylation

A thiolate displaces a leaving group.

Thiol Oxidation

Thiol Oxidation

Two thiols oxidize to a disulfide.