Organic Chemistry 354 Quiz - October 15, 1999

Dr. Sundin

1. Give the structure of the mononitro product obtained in largest yield by the nitric acid, sulfuric acid treatment of the ester below. Very briefly explain why your product was obtained in largest yield.

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2. Draw meso-2,3-dibromobutane using the dashed line, wedge technique. Answer

3. In each of the following mark each chiral carbon with an asterisk (*) AND tell how many stereoisomers are possible for each compound.

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4. Compound A, C6H12, is optically active. Carbon-13 NMR revealed that A had six different carbon atoms. A reacted with a basic permanganate solution to give a brown-black precipitate. Treatment of A with hydrogen and a nickel catalyst gave B, C6H14. B was found to be optically inactive. Additionally, carbon-13 NMR revealed that B had only four different carbon atoms. Give logical structures for A and B. Answer

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