Organic Chemistry 354 Quiz - September 3, 1999

Dr. Sundin

1. Compound A, C4H8Br2, was shown by mass spectrometry to have the two bromine atoms on two adjacent carbon atoms.

a. Draw the structures of three possible C4H8Br2 isomers which would have the two bromine atoms on adjacent carbon atoms. Answer

b. C-13 nmr spectroscopy revealed that compound A had three different carbon atoms. Draw the structure of A? Answer

2. Compound B, C3H8O, was shown by C-13 nmr spectroscopy to have three different carbon atoms.

a. Draw the structures of two possible C3H8O isomers with three different carbon atoms. Answer

b. Infrared spectroscopy revealed that B had an -O-H group in it. Draw the structure of B. Answer

c. Draw the structure of a C3H8O isomer which does not have three different carbon atoms. Answer

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