Download Chemistry Exam I, Fall 2006: IUPAC Names, Lewis Structures, Resonance, Conformations - Pro and more Exams Organic Chemistry in PDF only on Docsity! Seat No. _______________ LAST NAME Section ______A_____ FIRST NAME There are 7 pages to this exam. Check to make sure you have a complete exam. PLEASE ALSO PRINT YOUR NAME ON THE TOP OF THE BACK OF THE LAST PAGE OF THE EXAM CHEMISTRY 331 EXAM I Fall 2006 (9/12/06) I. (22 points) II. (16 points) III. (8 points) IV. (12 points) V. (6 points) VI. (10 points) VII. (14 points) VIII. (12 points) TOTAL (100 points) Seniors graduating Fall 06 please check box Seniors will not be excused from final. 2 I. (22 points). Give IUPAC names for the following compounds. A. CH3CH2CH2CHCH2CHCH2CHCH3 CH3CH2CH3CH2 CH3 ____________________________________ CH3CH2 CH2CH2CH2CH3 B. CH(CH3)2 ____________________________________ (CH3)2CHCH2CHCH2CHCH2CH3C. CH2 CH2CH2CH3CH3CH2CH2 ____________________________________ D. Cl Br ____________________________________ E. C C(CH3)3 CHCH2 CH CH3CH2CH2CH2 (CH3)2 CH2CH2CH3 CH3 ____________________________________ Draw the structures for the following names (show all hydrogens). F. isobutylcycloheptane G. (4 pts) trans-1,2-di-sec-butylcyclopropane 5 VI. (10 points) A. (6 points) Consider rotation about the C2-C3 bond of pentane A. CH3 CH2 1 2 A CH2 CH2 3 4 CH3 5 Complete the Newman projections to show conformations which fit the following descriptions. 1. The gauche conformation C H H 2. The less stable eclipsed conformation C H H B. (4 points) One of the conformations of methylcyclohexane is structure B. Only the methyl group and the hydrogen atom attached to carbon 1 are shown. Conformation B undergoes a ring flip to form conformation C. On the cyclohexane structure below, complete C by drawing in the methyl group and the hydrogen atom attached to carbon 1. B C H CH3 1 6 VII. (14 points) A. Complete the structures below to show ALL constitutional isomers (note: constitutional isomers only, no stereoisomers) of the substituted cyclohexanes that have the formula C8H16. Be sure to show all hydrogens. There are no more than 6 constitutional isomers and there may be fewer. Cross out any boxes that are not used. Points will be deducted for duplicate or incorrect structures. C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C B. Circle all constitutional isomers that can exist as a pair of cis-trans isomers. 7 VIII. (12 points) A. Draw the structure of the product(s) of the following reaction (show formal charges if appropriate). BF3 + (CH3)3N B. Draw the structure of the conjugate acid of a ketone that has 4 carbon atoms. C. Draw a pair of stereoisomers that are cyclopentanes and have the molecular formula C7H14. D. Draw the structure of a 5-carbon atom molecule that has only primary hydrogen atoms.
