Help Identifying a unknown aromatic ketone-we're stuck in a rut

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SUMMARY

The discussion centers on identifying an unknown aromatic ketone with a boiling point of approximately 214 degrees Celsius, soluble in sulfuric acid, and exhibiting specific IR peaks at 3000-2900, 1700, 1500-1400, and 1250. The compound is described as a very pale yellow liquid with a scent reminiscent of Vicks Vapor Rub. The participants have ruled out 2-decanone due to its non-aromatic nature and are seeking further testing methods and potential compound suggestions.

PREREQUISITES
  • Understanding of infrared spectroscopy (IR) and its application in organic compound identification.
  • Knowledge of aromatic ketones and their chemical properties.
  • Familiarity with boiling point determination and its relevance in compound identification.
  • Experience with solubility tests, particularly in sulfuric acid.
NEXT STEPS
  • Research methods for performing NMR spectroscopy to gain further insights into the compound's structure.
  • Explore the use of mass spectrometry for molecular weight determination and fragmentation patterns.
  • Investigate additional functional group tests that can confirm the presence of ketones and aromaticity.
  • Review literature on aromatic ketones with similar boiling points and IR spectra for potential matches.
USEFUL FOR

Chemistry students, organic chemists, and laboratory technicians involved in compound identification and analysis, particularly those focusing on aromatic compounds and ketones.

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Help! Identifying a unknown aromatic ketone--we're stuck in a rut!

Homework Statement


My 12th grade O'chem lab has been given an unknown organic compound. We have tested it and know the following:
BP-~214 degrees C
Soluble in H2SO4
Neutral compound
Aromatic ketone
No Nitrogen present
Physical description: very pale yellow liquid, smells like a very chemical version of Vic's Vapor Rub

We were also given an IR to analyze, which yielded very similar results to 2-decanone (which is what we thought it was until we found out it was aromatic). Now we have run out of ideas. I have sifted through close to 1000 IR specs, and all I know is what it is not. Major IR peaks are 3000-2900, 1700, 1500-1400, 1250.

I'm looking for suggestions as to further tests we can run, possible compounds that fit this description, anything. Thanks!


Homework Equations





The Attempt at a Solution

 
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What other types of testing are you equipped for and prepared to perform?
 


What's your evidence that it is aromatic? What's your evidence that it contains a ketone?