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EFS04 - State University of New York at Stony Brook...

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1 State University of New York at Stony Brook Department of Chemistry CHE 322, Organic Chemistry II Final Exam May 14, 2004 Form I Please answer all questions specifically, concisely, and readably in he designated spaces on the answer sheet, which we will collect at the end of the exam. Your Student Identification Number must be written and coded on the answer sheet, and your printed name and signature must be entered at the upper right. Think before writing. Include stereochemistry wherever relevant. Use the fronts and backs of the question pages for scratch work. Since the answer sheets will not be returned, we suggest that you record your answers on the question pages for comparison with the answers, which will be posted on Blackboard. Numerical grades will also be posted there. The first sixteen questions are multiple choice, worth seven points apiece. Enter your choices (only one per question) into spaces 1-16 of the answer sheet. Some useful information: Amino acids, RCH(NH 3 + )CO 2 - and pK a ’s : Asparagine, R = -CH 2 C(=O)NH 2 2.02, 8.80 Aspartic Acid, R = -CH 2 COOH 2.10, 3.86, 9.82 Cysteine, R = -CH 2 SH 2.05, 8.00, 10.25 Leucine, R = -CH 2 CH(CH 3 ) 2 2.33, 9.74 Lysine, R = -(CH 2 ) 4 NH 3 + 2.18, 8.95, 10.53 Phenylalanine, R = -CH 2 Ph 2.58, 9.24 Serine, R = -CH 2 OH 2.21, 9.15 Histidine, 1.77, 6.10, 9.18 NAD + = nicotinamide adenine dinucleotide Potassium phthalimide = FAD = flavin adenine dinucleotide PCC = pyridinium chlorochromate N N H R = N O O K
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2 1. The herbicide Propranil, shown below, is synthesized commercially from chlorobenzene. Which sequence of reactions would be most effective for carrying out this synthesis? A. Chlorination, nitration, reduction, acylation. B. Chlorination, reduction, nitration, acylation. C. Nitration, chlorination, reduction, acylation. D. Nitration, reduction, chlorination, acylation. E. It doesn’t matter; they would all work equally well.
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