The mass spectrum of ethyl butyrate shows two even-numbered fragments: at m>z 60 and m>z

Chapter 21, Problem 21-65

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The mass spectrum of ethyl butyrate shows two even-numbered fragments: at m>z 60 and m>z 88. These ions can be explained by a double McLafferty rearrangement: an initial McLafferty followed by a second rearrangement on the ion from the first. Show the cyclic transition states implicated in the two rearrangements, as well as the structures of the expected ions of masses 88 and 60. (Hint: begin with the ester side.) O O ethyl butyrate, mw 116

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