Your UANet ID: _____________________ Chemical Thinking U2 M2: Discussion 7 | 1

Analyzing Smells
Chemical compounds responsible for bad breath are the waste products of the anaerobic respiration of tongue
bacteria. Bacteria also produce the chemical compounds responsible for the bad smell of dead animals.

Combustion analysis of one of these smelly substances reveals

the following chemical composition: 54.49% C, 13.72% H, 31.79%
N. The MS and IR spectra of this substance are shown to the right.

1. Determine the empirical and molecular formulas of this

compound.

2. Propose one potential structure for this chemical substance.

Show how your proposed structure could lead to the MS
fragmentation pattern and IR absorption bands in the
spectra.

3. Propose other molecular structures that could generate similar IR spectra.

Your UANet ID: _____________________ Chemical Thinking U2 M2: Discussion 7 | 2

4. Unknown B is a liquid with a pleasant banana smell

with a boiling point of 127ºC. Elemental analysis
results show that it has an empirical formula of
C3H6O. Use this and the IR-MS data to determine
the molecular structure of this compound. Clearly
justify your reasoning.

5. The substance mainly responsible for the odor often

associated with fouling fish has the chemical
formula C3H9N. Propose a reasonable structural
formula and assign structures to at least 3 peaks in
the MS spectrum.
Your UANet ID: _____________________ Chemical Thinking U2 M2: Discussion 7 | 3

6. A substance with a pungent odor present in

vanilla has the empirical formula C2H4O. Use
this information and the IR-MS data to
determine the structure of this compound.

7. An odorless gas used as a refrigerant has

the empirical formula of C3F6O. Use this
information and the IR-MS data to
determine the structure of this compound.