Answered: Determining the Regioselectivity of…

Determining the Regioselectivity of Opening an Epoxide Ring What product is formed when 2,2-dimethyloxirane is treated with each set of reagents: −OCH3 followed by H2O, or CH3OH and H2SO4?

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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.52P: Claisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads...

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

Determining the Regioselectivity of Opening an Epoxide Ring

What product is formed when 2,2-dimethyloxirane is treated with each set of reagents: ⁻OCH₃ followed by H₂O, or CH₃OH and H₂SO₄?

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.

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