An unknown, foul-smelling hydrocarbon gives the mass spectrum and infrared spectrum shown.

(a) Use the mass spectrum to propose a molecular formula. How many elements of unsaturation are there?

(b) Use the IR spectrum to determine the functional group(s), if any.

(c) Propose one or more structures for this compound. What parts of the structure are uncertain? If you knew that hydrogenation of the compound gives n-octane, would the structure still be uncertain?

(d) Propose structures for the major fragments at 39, 67, 81, and 95 in the mass spectrum. Explain why the base peak is so strong.

Transcribed Image Text:

100 41 80 39 60 40 81 67 20 M 95 110 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 mlz abundance