N H OH. Amine Alcohol Alkane. Amide A B C D

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1 ame Exam 1 SLUTI Please work in the space provided. Box your answers to set them off. The last page may be torn off and used for scratch paper. ing all materials up when you are finished with the exam. Good luck! 1. Analyze the structure of Tilisolol (Selecal TM ), a beta blocker used for a variety of cardiac indications. [6] a) What is the formula for the molecule? b) What functional groups are present in the molecule? Circle the functional group on the structure and name it next to your circle. Ether Aromatic Ring Amine Alcohol Alkane C Amide 2. Consider the four structures drawn below: [8] 2 C 2 C 2 C 2 C 3 C 3 C 3 C 3 C A B C D a) Which structure is not an allowable resonance contributor/structure for the compound? Explain your choice. Structure C is not allowable. The structure violates the octet rule for the nitrogen! itrogen cannot go beyond an octet. b) ut of the remaining structures, which is the best resonance contributor/structure for the compound? Explain your choice. Structure B is best. This structure puts the negative charge on the most electronegative element, every atom has an octet, and bonding is maximized without violating the octet rule. 3. The connectivity of carbon oxysulfide is -C-S. [8] a) Draw the complete Lewis structure for the molecule. b) What is the hybridization and molecular geometry about the central carbon? c) Is the molecule polar? If so, which way does the dipole point? C S The carbon is sp-hybridized and has a linear geometry. Since oxygen is more electronegative than sulfur, there is a dipole in the molecule, pointing towards the oxygen side of the molecule. Exam 1 all 2008 Page 1 of 6

2 4. omenclature. [12] a) Draw the following molecules from the IUPAC names provided. trans-2-bromo-4-t-butylcyclopentanone 3-bromo-4-methyl-4-hexenal b) Provide IUPAC names for the following molecules. Cl C 3 7-chloro-5-isopropyl-2,4-heptanediol 1,1,2,5-tetrafluoro-3,4-dimethylhexene 5. The following IR spectrum is for C Based on the IR spectrum, is the molecule cyclohexane, 2,3-dimethyl-2-butene (an internal alkene) or 2,3-dimethyl-1-butene (a terminal alkene)? ow do you know this? Support your answer with at least two specific peaks and their significance. [8] sp 2 C- C=C o C=C bond C=C bond no sp 2 C- C=C bond sp 2 C- The IR shows both a C=C double stretch at ~1650 cm -1 and an sp 2 -hybridized C- stretch at 3100 cm -1 indicates an external alkene, such as 2,3-dibromobutene. Exam 1 all 2008 Page 2 of 6

3 6. Draw both chair conformers for the following substituted cyclohexane ring. Circle the conformer that is more stable. [8] C 3 3 C C 3 Even though there is only one equatorial group, the t-butyl group is so sterically large that it forces the ring into a position where it is equatorial. 7. The following three spectra correspond to three of the four molecules below. All molecules have the formula C Match the IR spectrum to the appropriate compound, and give a brief but specific reason for your choices. [12] Compound A Compound B Compound C Compound D sp C- stretch C-triple-C stretch C- stretch This spectrum belongs to: Compound D Reason: The spectrum shows a C-C triple bond stretch at 2100 cm -1, and more importantly, an sp-hybridized C- stretch at 3300 cm -1. nly compound D has a hydrogen attached to the triple bond. This peak differs from an alcohol peak (which would show up at the same place) because it is not broad, like a hydrogen-bonded alcohol peak would be. Exam 1 all 2008 Page 3 of 6

4 C= stretch C- stretch This spectrum belongs to: Compound B Reason: The carbonyl stretch at 1720 cm -1 narrows it down to compounds A or B. however, the C- stretching frequency at 1190 cm -1 indicates an ester, not a ketone. - stretch This spectrum belongs to: Compound C Reason: The large stretch between cm -1 makes it obvious! The C-C triple bond stretch does not show up, since the molecule is symmetric. 8. Draw two examples of a molecule (for each condition) that has the formula C 6 12 and: [6] a) That exhibits angle strain (or ring strain). (provide two examples) Three or four-membered rings only! ive and six-membered rings do not show angle (ring) strain. b) That exhibits a peak in the IR between cm -1. (provide two examples) An IR peak at cm -1 indicates an alkene. Any 6-carbon alkene would work. Exam 1 all 2008 Page 4 of 6

5 9. or the molecule 2-isopropyl-5-methylcyclohexanol, draw the lowest possible energy chair conformer for the molecule, then translate that structure to a flat hexagon structure with wedges and dashes to indicate the relative positions of the 3 substituents. [6] "down" 3 C "down" "up" The lowest energy conformer has all groups in equatorial positions. 10. Draw a line structure for 1-bromo-2-methylbutane, and then draw and label the following three ewman projections for the structure: The LWEST energy conformation, the SECD LWEST energy conformation, and the IGEST energy conformation. Your ewman projections should be looking down the C1-C2 bond. [10] LWEST SECD LWEST IGEST C 3 C 2 C 3 3 C 2 C C 3 C 2 C 3 C 3 3 C With only one hydrogen on carbon 2, all of the staggered conformations will have a gauche interaction with the bromine on carbon 1. The lowest energy conformation has the bromine in a gauche interaction with the methyl group, which is smaller than the ethyl group. The high energy conformers are always eclipsed conformers. The highest energy conformer will have the two largest groups (the bromine and the ethyl) eclipsed. 11. Which of the following molecules has the lowest boiling point? [2] More branching! Exam 1 all 2008 Page 5 of 6

6 12. itroamines are common functional groups in highly reactive molecules (such as plastic explosives). The sample structure below has all electrons represented. or the structure given, assign formal charges to the atoms that need it, and then draw any significant resonance structures for the molecule. [6] 3 C 3 C 3 C 3 C Another structure can be drawn with a double bond between the nitrogens, but is has extra formal charges, therefore it is not a significant structure. 13. Completely explain why the staggered conformation in ethane is more stable (lower energy) than the eclipsed conformation in ethane. Use words and/or pictures in your explanation. [6] The staggered conformation gives the largest dihedral angle between neighboring groups, minimizing torsional strain and steric hinderance between the C- bonds on carbon 1 and carbon 2. The staggered conformation also allows for overlap between a C- bond on one carbon and the!* orbital on the other carbon, allowing the electron density to be delocalized into a larger area. 14. In an alkyne, the triple bond consists of: [2] a) Two sigma bond formed from p orbitals and one pi bond formed from sp-hybrid orbitals on each carbon. b) ne sigma bond formed from hybrid orbitals and one pi bond from p orbitals on each carbon. c) Three bonds formed from the pairs of p x, p y, and p z orbitals on each carbon. d) ne sigma bond formed from hybrid orbitals and two pi bonds from p orbitals on each carbon. Exam 1 all 2008 Page 6 of 6

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