McLafferty rearrangement

The McLafferty rearrangement is an organic reaction seen in mass spectrometry. A mass spectrometer breaks apart the molecule being studied.  The molecule breaks apart in consistent ways that chemists can predict. Most of the time, a carbon-carbon bond breaks and the atoms do not jump across the break between the fragments. The McLafferty rearrangement is an example of a hydrogen atom jumping to the other fragment as a part of the process of the bond breaking.  It happens in an organic molecule containing a keto-group.

 The reaction 
The American chemist Fred McLafferty was the first to describe the reaction in 1959.

The keto-group undergoes β-cleavage, with the gain of the γ-hydrogen atom. This rearrangement may take place by a radical or ionic mechanism.
Related pages
α-cleavage

References

Further reading

Other websites
 Fred McLafferty Faculty Webpage at Cornell University

Category:Mass spectrometry
Category:Rearrangement reactions