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McLafferty Rearrangement

The McLafferty rearrangement is a reaction observed in mass spectrometry where a molecule containing a keto-group undergoes β-cleavage, gaining the γ-hydrogen atom. This rearrangement occurs by either a radical or ionic mechanism. Alpha cleavage refers to breaking the carbon-carbon bond adjacent to a carbon bearing a functional group. In mass spectrometry of carbonyl compounds, alpha cleavage often competes with the McLafferty rearrangement.

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3K views3 pages

McLafferty Rearrangement

The McLafferty rearrangement is a reaction observed in mass spectrometry where a molecule containing a keto-group undergoes β-cleavage, gaining the γ-hydrogen atom. This rearrangement occurs by either a radical or ionic mechanism. Alpha cleavage refers to breaking the carbon-carbon bond adjacent to a carbon bearing a functional group. In mass spectrometry of carbonyl compounds, alpha cleavage often competes with the McLafferty rearrangement.

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Zafar Iqbal
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© Attribution Non-Commercial (BY-NC)
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McLafferty rearrangement The McLafferty rearrangement is a reaction observed in mass spectrometry.

It is sometimes found that a molecule containing a keto-group undergoes -cleavage, with the gain of the -hydrogen atom. This rearrangement may take place by a radical or ionic mechanism. The reaction A description of the reaction was first published by the American chemist Fred McLafferty in 1959.

Alpha cleavage
From Wikipedia, the free encyclopedia

Alpha cleavage, (-cleavage) refers to the act of breaking the carbon-carbon bond, adjacent to the carbon bearing a specified functional group. 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) 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.

In molecules containing carbonyl groups, alpha cleavage often competes with McLafferty rearrangement.

http://science.uvu.edu/ochem/index.php/alphabetical/a-b/alpha-cleavage/

Alpha Cleavage
Alpha cleavage in mass spectrometry is a characteristic fragmentation of the molecular ion derived from carbonyl compounds, in which the bond linking the carbonyl carbon to the atom occuping an alpha position breaks. eg:

http://science.uvu.edu/ochem/index.php/alphabetical/a-b/beta-cleavage/

Beta cleavage in mass spectrometry is a characteristic fragmentation of the molecular ion derived from some organic compounds, most notably alcohols, ethers, and amines, in which the bond connecting alpha- and beta-carbons break. eg:

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