Chemistry Workshops

for Organic Chemistry

Chapter 12 Workshop Problems

Mass Spectrometry / Exam Review


1. Attached is a low resolution mass spectrum of a compound with formula C3H7ClO .

 

Describe how the presence of chlorine is indicated by some of the patterns.

Identify all of the peaks in the spectrum by structure.

Identify logical pathways to form each of the peaks.

Can you conclusively identify the original compound, or are there different isomers that could give this mass spectrum?

2. Mass spectrometry is traditionally run so as to observe positive ions. However, minor modifications allow for observations of negative ions.

Describe what instrumental modifications might be used to observe a negative ion mass spectrum.

Describe what different patterns of fragmentation might be observed in negative ion mass spectra. What might be a common fragment observed from

alkyl halides
alcohols
alkenes

3. Exam review:

Add alkynes, ethers, and epoxides to your chart of functional group families. Write as many reactions as you can that interconvert the various functional group families.

Show how to synthesize the following compounds from acetylene and alkyl halides, plus any needed solvents and inorganic reagents.