CHEM 310 Exam 1Dr. HannaFebruary 7, 2007Honor Pledge:In Part V of the Winthrop University Student Conduct Code, it is stated that “A fundamental tenet of all institutions of higher learning is academic honesty. … Misrepresentation of someone else’s work as one’s own is a most serious offense in any academic setting. … Academic misconduct includes but is not limited toproviding or receiving assistance in a manner not authorized by the professor in the creation of work to be submitted for academic evaluation including papers, projects, and examinations …”By my signature below, I pledge that I did not commit academic misconduct (cheat) on this examination.____________________________________ ______________________________Printed Name SignaturePart 1 _____________/20Part 2 _____________/30Part 3 _____________/15Part 4 _____________/20Part 5 _____________/15Total _____________/100Page 2Part 1: Nomenclature (20 pts)1a. Write IUPAC names for the following compounds (indicate stereochemistry where required):i) ii) iii) 1b. Draw structures corresponding to the following IUPAC names:i) (E)-5-Ethyl-8-methylnon-4-eneii) cis-1-Ethyl-2-isopropylcyclopentaneCH3C CH3CH3CH2CHCH3CH2CH CH3CH2CH3CH3CH3CH3CH3CH2CH3CH3CCH3CH3CH3Page 3Part 2: Structure and Bonding (30 pts)2a. Draw Lewis structures for the following compounds (include resonance forms if applicable). Indicate the molecular shape (e. g. linear, trigonal pyramidal, etc.) around the central atom.i) CO3-2ii) CO2iii) CHCl32b. Provide the hybridization of and the approximate bond angles around the indicated atom in the following molecules:Hybridization Bond Anglei) ii) iii) CH3C NCOHOHOHOHOHOCH3CH2OCH2CH3Page 42c. Indicate whether the compounds in each pair are cis-trans diastereomers, constitutional isomers, oridentical:i) ii) iii) 2d. Sighting down the C2-C3 bond of n-pentane, there are 2 types of staggered conformations. Draw Newman projections for both, indicate the most stable conformation, and explain your choice.2e. Which is a more stable compound – cis-1-tert-butyl-3-methylcyclohexane or trans-1-tert-butyl-3-methylcyclohexane? Draw chair conformations of both, and explain your answer.CH3HHCH3CH3HCH3HandHBrHClBrClHHandCH2CH3CH3andCH2CH3CH3Page 5Part 3: Functional Groups (15 pts)Identify the functional groups present in the following compounds:ONHCH3OOOOCH3CH3CH3ColchicineABC OCH3CH3OHONaproxenD NorethindroneC CHOHCH3OEF RadicininCH3OOOOOHCH3G HA = _________________________________B = _________________________________C = _________________________________D = _________________________________E = _________________________________F = _________________________________G = _________________________________H = _________________________________Page 6Part 4: Acids and Bases (20 pts)4a. Circle the stronger acid in each pair and state the major factor that accounts for the acidity difference:Major Factori) ______________________ii) ______________________iii) ______________________iv) ______________________4b. The pKa of propanoic acid is about 5, while the pKa of 1-propanol is about 16. Will the following reaction take place? Explain.OHO-O+O-OHO+Li+Li+1-PropanolPropanoic acidorNH3FHCH3OHOCH3COHHHorClHPH3orCH3OHorCH3SHPage 7Part 5: Reaction Mechanisms and Energy Diagrams (15 pts)5a. Predict the product of the following reaction:+H I5b. Write a mechanism for the reaction in 5a.5c. Sketch a reaction energy diagram for the reaction above. Assume that the product is of lower energy than the reactants, and the first step is the rate limiting step (the slowest step). Label the reactants, products, intermediate, and transition states on your energy