Download Organic Chemistry II - Final Exam | CHEM 2313 and more Exams Organic Chemistry in PDF only on Docsity! Name_______________________________ Chem 2313 Organic Chemistry Lecture Seton Hall University Instructor: Prof. John R. Sowa, Jr. December 20, 2006 Final Exam 150 points Q1________ Q2________ Q3________ Q4________ Q5________ Q6________ Q7________ Q8________ Total_______ Good Luck! 1) (21 points) Nomenclature a) (12 points), 3 each) Write the IUPAC names for the following compounds. Indicate stereochemistry where appropriate. i) b) Cl H O c) d) (Hint: E or Z?) OH Br b) (9 pts, 3 ea) Draw the structure of the following compounds: i) trans-2-methylcyclopentanol ii) S-2-bromobutane iii) 3-methyl-2-pentanone c) (6 pts, 3 ea) Consider the type of conformation necessary for an E2 reaction. i) Which conformation allows for elimination of H1 and Br. What is the product of this reaction and correct stereochemistry of the product? ii) Which conformation allows for elimination of H2 and Br. What is the product of this reaction and correct stereochemistry of the product? d) (2 pts) Consider the relative energies of the above conformations, which elimination is favored H1/Br or H2/Br. Thus, which product is favored? 4) (18 points) Acid/Base and Nucleophile Chemistry a) (6 pts, 2 ea) In each pair of compounds, circle the stronger acid. F3C OH O i) iii) ii) vs. H3C OH O OH OH vs. vs. H3C CH3 O H3C CH3 b) (6 pts, 2 ea) In each pair of compounds, circle the stronger base. i) iii) ii) vs. NH2 NH2 vs. CH3O CH3OH vs.CH3OH CH3NH2 c) (6 pts, 2 ea) In each pair of compounds, circle the stronger nucleophile. i) iii) ii) vs.CH3O CH3OH vs.CH3OH CH3NH2 vs.CH3OH CH3NH2 iv) vs.I Cl 5) (24 points, 3 pts ea) Transformations. Complete the following transformations by supplying the missing reagents, reactants or products. Show correct stereochemistry where appropriate. i) iii) S O O Cl pyridine BA N N CO2EtEtO2C PPh3 F ii) iv) G Br2, H2O Cl SPh OH 1) BH3-THF 2) H2O2, NaOH(aq) CH3S Na DMSO solvent C OH (Hint: Mitsonubo reaction) D NaOH (aq) or NaH (org) E
