Alcohols, Ethers, and Thiols - What Are Epoxides?

6 important questions on Alcohols, Ethers, and Thiols - What Are Epoxides?

How are epoxides synthesized?

On an industrial scale ethylene and oxygen are passed over a silver catalyst.
On lab scale most commonly used is peroxyacetic acid.
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What stereoisomers are formed in epoxidation reactions?

The epoxidation reaction is stereoselective. Groups that are cis in the alkene will be cis in the epoxide.
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Ethers normally don't react in the presence of an acid-catalyst, why do epoxides do?

The normal bond angle of a sp3 hybridized atom is 109.5o in epoxides the bond angle of the three-membered ring is 60o. Therefor epoxides undergo ring opening reactions with a variety of nucleophiles.
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What product does the acid-catalyzed hydrolysis of epoxycycloalkane yield?

A trans-1,2-cycloalkanediol.
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What are the steps in the SN2 mechanism of acid-catalyzed epoxide ring opening reactions?

1. addition of a proton to the oxygen
2. Reaction on an electrophile and a nucleophile (water) and the breaking of one of the C-O bonds.
3. Removal of a proton.
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What are the three most important nucleophilic ring-opening reactions?

1. The addition of ammonia
2. The acid-catalyzed hydration
3. The reaction with a thiol salt.
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