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Organic Chemistry 1

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The Claisen Rearrangement: Vinyl vs. Phenyl

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Allyl vinyl ethers rapidly and easily rearrange to ketones or aldehydes via the Claisen rearrangement (top reaction).

Image by Daniel J. Berger. Created for Albert.io. Copyright 2016. All rights reserved.

While allyl phenyl ethers also undergo this reaction (bottom), it is much slower because

A

the rearrangement breaks the six-membered ring.

B

the rearrangement disrupts conjugation between oxygen and the ring.

C

the rearrangement requires disruption of aromaticity.

D

the rearrangement is geometrically difficult.