Frequently Asked Question

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Hydroperoxide alpha Hydrogen in ether

Accepted Answer

Alpha hydrogen is the hydrogen atom attached to the carbon next to the oxygen atom in an ether group. The alpha hydrogen in ethers is acidic, meaning it can be removed by a base to form an alkoxide ion. The alkoxide ion is a strong nucleophile and can react with electrophiles such as alkyl halides to form ethers. The acidity of the alpha hydrogen in ethers is due to the resonance stabilization of the alkoxide ion. The alkoxide ion can resonate with the ether oxygen to form two resonance structures, both of which have a negative charge on the oxygen atom. This negative charge helps to stabilize the alkoxide ion and makes it a stronger base than the hydroxide ion.


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