Mass Spec- breaking the benzene ring

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Discussion Overview

The discussion revolves around the analysis of a compound with the molecular formula C8H8O2, specifically focusing on the interpretation of its mass spectrum. Participants explore the stability of various fragments observed in the spectrum, particularly the peak at m/z 91, and the potential structures associated with other peaks at 118 and 65. The conversation includes considerations of the benzene ring's stability and the possibility of its fragmentation.

Discussion Character

  • Homework-related
  • Exploratory
  • Debate/contested

Main Points Raised

  • One participant proposes that the peak at m/z 91 corresponds to a structure involving a benzene ring with an attached hydrogen and carbon.
  • Another participant questions whether the compound actually contains a benzene ring, suggesting alternatives like cyclopentadiene or fulvene derivatives.
  • A later reply indicates that the structure at m/z 91 is not benzene but rather a tropylium ion.
  • Participants express uncertainty about the possibility of breaking the benzene ring, acknowledging its stability due to delocalized electrons.
  • One participant mentions the need for clarification on the fragmentation of the benzene ring and expresses confusion about potential alternative solutions.
  • Hints are provided regarding the tropylium ion and its fragmentary pattern, suggesting further research on the topic.

Areas of Agreement / Disagreement

Participants do not reach a consensus on whether the compound contains a benzene ring, with some suggesting alternatives and others maintaining that it could be benzene. The discussion remains unresolved regarding the fragmentation of the benzene ring and the interpretation of the mass spectrum peaks.

Contextual Notes

Participants reference specific structures and their stability, but there are limitations in the assumptions made about the compound's identity and the potential for fragmentation. The discussion also reflects a dependence on the syllabus content, which may restrict the exploration of certain chemical structures.

leah3000
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Homework Statement


the molecular formula of the compound under analysis is C8H8O2 = Mr of 136
the mass spectrum shows the peak at 91 to be the most stable. I'm supposed to obtain structures representing the peak at 91 as well as at 118 and 65


The Attempt at a Solution



I represented 91 as the benzene ring with H-C(-H) attached

@ 118 H-C-C(=O) is attached

I'm having trouble getting the structure at 65

C8H8O2 would be represented as the benzene ring with H-C(-H)-C(=O)-O-H attached.
The only way I'm seeing to obtain 65 is if i remove the attached group from C8H8O2 along with a C from the benzene ring. Is this even possible? Because I know the benzene ring is very stable...:confused:
 
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Are you positive this compound contains a benzene ring?

Could it be a cyclopentadiene or fulvene derivative?
 
PhaseShifter said:
Are you positive this compound contains a benzene ring?

Could it be a cyclopentadiene or fulvene derivative?

well...those groups aren't on the syllabus I'm studying. Benzene and phenol are the only aromatic compounds I'm studying. Can benzene be an option?
 
leah3000 said:

Homework Statement


the molecular formula of the compound under analysis is C8H8O2 = Mr of 136
the mass spectrum shows the peak at 91 to be the most stable. I'm supposed to obtain structures representing the peak at 91 as well as at 118 and 65


The Attempt at a Solution



I represented 91 as the benzene ring with H-C(-H) attached

@ 118 H-C-C(=O) is attached

I'm having trouble getting the structure at 65...

It's not benzene anymore... it's tropylium (m=91).
 
chemisttree said:
It's not benzene anymore... it's tropylium (m=91).

I don't understand:confused:

maybe i explained it wrong? i was trying to describe the structure i assumed the fragments to be. But what I'm not clear on is if it's ever possible to break the benzene ring. I know the ring is stable due to the delocalised electrons...so I don't understand why the benzene ring itself would fragment. I have no idea as to what other solution it could be. :redface:
 
leah3000 said:
...I'm not clear on is if it's ever possible to break the benzene ring.

That's why I gave you a hint... tropylium ion. Very interesting fragmentary pattern for tropylium ion... nuff said.

I know the ring is stable due to the delocalised electrons...so I don't understand why the benzene ring itself would fragment. I have no idea as to what other solution it could be. :redface:
See above.

hint: google "tropylium fragmentary pattern"
 
thank you!
 
De nada!
 

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