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McLafferty rearrangement facts for kids

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The McLafferty rearrangement is a special way that molecules break apart when scientists study them using a machine called a mass spectrometer. Imagine you have a LEGO model, and you want to see what pieces it's made of. A mass spectrometer is like a super-strong wind that blows the LEGO model apart. Most of the time, when a molecule breaks, the pieces just split. But in a McLafferty rearrangement, a tiny hydrogen atom actually jumps from one part of the molecule to another part as it breaks! This special jump happens in molecules that have a specific part called a "keto-group" (which is a carbon atom double-bonded to an oxygen atom, like C=O).

What is the McLafferty Rearrangement?

This cool chemical trick was first described in 1959 by an American scientist named Fred McLafferty. He figured out how this specific type of molecular breaking happens.

When a molecule with a keto-group goes through a McLafferty rearrangement, a bond breaks a few atoms away from the keto-group. At the same time, a hydrogen atom from a specific spot (called the "gamma" position) moves over to the oxygen atom of the keto-group. This makes the molecule split into two new, smaller pieces.

McLafferty rearrangement
An example of how the McLafferty rearrangement happens. See the hydrogen atom (H) move!

Scientists use this knowledge to understand what different molecules are made of. By looking at the pieces a molecule breaks into, they can figure out its original structure, almost like solving a puzzle!

Related Chemical Ideas

  • Alpha cleavage: Another way molecules can break apart in a mass spectrometer.
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