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the electron ionization mass spectrum of a small neutral molecule shows a base peak at 27 and a smaller peak at 26 with a relative abundance of 20%. Deduce the structure of the unknown compound.  Draw a cation that corresponds to this peak.

the electron ionization mass spectrum of a small neutral molecule shows a base peak at 27 and a smaller peak at 26 with a relative abundance of 20%. Deduce the structure of the unknown compound.  Draw a cation that corresponds to this peak.

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.25P
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the electron ionization mass spectrum of a small neutral molecule shows a base peak at 27 and a smaller peak at 26 with a relative abundance of 20%. Deduce the structure of the unknown compound. 

Draw a cation that corresponds to this peak.

2,2,4-trimethylpentane CH3 CH3 H3C H3C C C' H₂ CH CH3
Transcribed Image Text:2,2,4-trimethylpentane CH3 CH3 H3C H3C C C' H₂ CH CH3
Step 4: Consider common alkyl fragmentation patterns. Alkanes will often fragment to lose a diagnostic group. Calculate the difference between the molecular ion and the base peak. • If the difference is 15, that indicates loss of a CH3 radical • If the difference is 29, that indicates loss of an ethyl radical • If the difference is 43, that indicates loss of a propyl radical • If the difference is 57, that indicates loss of a butyl radical Consider the structure of 2,2,4-trimethylpentane. The mass spectrum of this structure shows a base peak at 57.
Transcribed Image Text:Step 4: Consider common alkyl fragmentation patterns. Alkanes will often fragment to lose a diagnostic group. Calculate the difference between the molecular ion and the base peak. • If the difference is 15, that indicates loss of a CH3 radical • If the difference is 29, that indicates loss of an ethyl radical • If the difference is 43, that indicates loss of a propyl radical • If the difference is 57, that indicates loss of a butyl radical Consider the structure of 2,2,4-trimethylpentane. The mass spectrum of this structure shows a base peak at 57.
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