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Unformatted text preview: INTRODUCTORY ORGANIC CHEMISTRY EXAM IB Professor Merlic UCLA I. BONDING AND STRUCTURE 1. Answer each question below relative to the structure of Dihydromevinoline (a drug that regulates blood pressure) given below. The letters refer to questions. H H O O HO O H O H H G F E D C B A A. (1) What is the geometry about this carbon atom? ________________________ B. (1) What orbitals does this carbon atom use for bonding? __________________ C. (1) Is this proton primary, secondary, or tertiary? ________________________ D. (1) What orbitals does this carbon atom use for bonding? __________________ E. (1) What term best describes this sigma bond? ____________________ F. (1) Which carbon, F or G, would be more reactive towards chlorination? ____ H. (1) What is the geometric descriptor for the ring fusion? ____________________ 2. A. (5) Draw ALL POSSIBLE resonance structures for the nitromethane anion, - CH 2 NO 2, and label the LOWEST and HIGHEST energy structures. and label the LOWEST and HIGHEST energy structures....
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