Alpha Cleavage
A radical cation localized on a heteroatom lone pair breaks the bond alpha to that atom, expelling a radical and leaving a resonance-stabilized even-electron cation such as an acylium or oxocarbenium ion. The largest alkyl radical is lost preferentially, which is why alcohols, amines, ethers and ketones give predictable dominant fragments.
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A radical cation localized on a heteroatom lone pair breaks the bond alpha to that atom, expelling a radical and leaving a resonance-stabilized even-electron cation such as an acylium or oxocarbenium ion. The largest alkyl radical is lost preferentially, which is why alcohols, amines, ethers and ketones give predictable dominant fragments.
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