Everything about Alpha Cleavage totally explained
Alpha cleavage, in
organic chemistry, refers to the act of breaking the
carbon-carbon bond, where one of the carbons bears a
functional group.
Generally this topic is discussed when covering
mass spectroscopy and occurs generally by the same mechanisms.
For example of a mechanism of alpha cleavage
An electron is knocked off an atom (usually by electron collision) to form a radical cation. Electron removal generally happens in the following order.
1. Lone pair electrons
2. Pi Bond Electrons
3. Lastly - Sigma Bond Electrons
One of the lone pair electrons moves down to form a pi bond with an electron from an adjacent (alpha) bond.The other electron from the bond moves to an adjacent atom (not one adjacent to the lone pair atom) creating a radical. This creates a double bond adjacent to the lone pair atom (oxygen is a good example) and breaks/cleaves the bond from which the two electrons were removed.
Example C-C-(O::)-H > C-C-(O:.+)-H > C' + (C=O:+)-H where : is a lone pair + is a positive charge and ' is a radical/free electron
In molecules containing carbonyl groups, often competes with
McLafferty rearrangement.
Further Information
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