1CHE 230 - Organic ChemistryExam 1, February 6, 2002Name Student ID No. Before you begin this exam: First: You are allowed to have a simple model set at your seat.Please put away all other materials. Second: Place your student identification on your desk. Aproctor will come around to check everyone’s ID. Third: Read through the entire exam. Yourgoal, as always, is to score as many points as possible. Do not waste time on problems that youcan’t do if there are others that look easy. Fourth: It is critically important that your answers bewritten in a clear, unambiguous manner. Answers in which your intentions are unclear will notreceive credit. Fifth: READ THE INSTRUCTIONS FOR EACH PROBLEM. You haveuntil 9:50 to complete this exam. There will be no extensions, so budget your time carefully.Problem Points Score1. 6 2. 8 3. 6 4. 10 5. 10 6. 20 7. 15 8. 9 9. 10 10. 6 Total 10021. (6 points) Calculate the molecular formula of each of the following compounds.OH__________________________________ __________________________________2. (8 points) Draw four different skeletal isomers of C7H12. Note: There are morethan four acceptable answers here – just draw any four. If you draw more than4, we will grade the first 4.33. (6 points) Provide a viable IUPAC name for the compound below. Be sure tospecify the stereochemistry.HF4. (10 points) Identify the hybridization of the indicated atoms.NNHCH3NOThis nitrogen is _____ hybridizedThis nitrogen is _____ hybridizedThis carbon is _____ hybridizedThis carbon is _____ hybridizedLysergic acid, diethyl amideNCNThis carbon is _____ hybridized45. (10 points) Classify each of the following pairs of compounds as either resonanceforms, conformational isomers, structural isomers, or stereoisomers.CH3HH HCH3HCH3HH CH3HH6. (15 points) Draw the Lewis dot structure (show DOTS!) and assign partialcharges for both carbons and for the nitrogen in this resonance form of methylisocyanide (below).CH3N C(5 points) Draw one additional resonance form for methyl isocyanide. Show theproper use of arrows: arrows for the motion of electrons and arrows to denoteresonance forms.CH3N C57. a) (5 points) Draw a Newman projection of propane in a staggeredconformation.b) (10 points) Draw the rotational energy diagram for propane. On yourdiagram clearly indicate the position of staggered conformations and eclipsedconformations. Your diagram should include rotation through any 2 staggeredand any 2 eclipsed conformations.EQ8. (9 points) How many p molecular orbitals (bonding plus antibonding) arepresent in each of the following:NCH3CH3CHCH3CH3CCH3CH369. (10 points) Nitrogen is more electronegative than carbon. Explain why 4-cyanoaniline (below) has nitrogens as both the positive and the negative end ofthe dipole. Note: a picture is worth a thousand words. DO NOT exceed thespace provided.H2N C NDipole10. (6 points) The lone pair on nitrogen in the compound below is NOT stabilized byresonance, despite the adjacent p bond. Explain why this is. Note: a picture isworth a thousand words. DO NOT exceed the space provided.NCOEND OF
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