Formation of epoxides from bromohydrins

by James

Description: Halohydrins treated with strong base (such as hydroxide ion) can form epoxides through an intramolecular SN2 reaction.
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{ 5 comments… read them below or add one }

Ola

Maybe I misssed something but I don’t understand why in the first example we get alkane instead of epoxide ?
Could you explain what is the reason?
Greetings

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james

It’s a typo. Thanks for pointing it out! Fixed.

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Ola

Maybe I misssed something but I don’t understand why in the first example we get alkane instead of epoxide ?
Could you explain what is the reason?
Greetings

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Miguel

Is it possible for a trans-1-chlorocyclopentan-2-ol to react with sodiumhydride and to form a epoxide and hydrogengas? Or does it not react in this way because of the steric hinderence and wil it form something else or will it not react at all?

If someone could help me out that will be awesome?

Greetings,

Miguel

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James

Yes, sodium hydride is a base, and it would deprotonate the alcohol to give an alkoxide and then form an epoxide.

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