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Chapter 22: Q1IC (page 571)

Draw a rearrangement like reaction D in figure 22-12 to show how m/z 58 arises from 4-methyl-2-pentanone.

Short Answer

Expert verified

The structure of the 4-methyl-2-pentanone is shown below :

Step by step solution

01

Mc- Lafferty Rearrangement :

The Mc- Lafferty Rearrangement is a characteristic fragmentation of the

molecular ion of a carbonyl compound containing at least one γ- Hydrogen.

It is an example of intramolecular rearrangement.

02

     Step 2 :  Showing Mc- Lafferty Rearrangement in  4-methyl-2-pentanone :

In the given compound a γ-Hydrogen or 4-H (on numbering from carbonyl carbon) is present. So, there is a possibility of a Mc- Lafferty Rearrangement . After fragmentation we get [a radical cation, mz= 58 . [ C3H0:(12×3)+1×6+16=36+6+16=58].

Hence , due to Mc- Lafferty Rearrangement mz= 58 arises from 4-methyl-2-pentanone.

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