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CHEMISTRY 1152 EXAM III Fall, 2002 NAME__________________________ All notes, books, etc., must be placed out of sight. Please read each of the problems carefully. If something is not clear, please ask. The exam consists of 11 problems on 4 pages with some extra credit on the fifth page. Make sure your exam is complete. The exam is worth 100 points with each of the problems labeled as to its point value. Answers should be placed in the space provided. Write legibly--if I cannot read it--it is wrong. Please include an explanation whenever asked to or whenever necessary to make your answer clear. Please put your name on every page of the exam. As usual, no cheating is allowed. Good Luck!!! Chemistry 1152 1 Name________________________ 1.(12) Name each of these structures correctly using systematic names… A. B. O O C CH2 H3C CH2 H3C C. N CH3 CH3 D. + H3N CH3 _ Cl 2.(12) Draw correct structures for each of the following… A. 4-methylpentanal B. 2-bromo-4-methylbenzaldehyde C. amino acid in acidic solution D. 2-aminobutane 3.(3) The amide C5H11NO yields ethylamine on hydrolysis. Identify the other product. 4.(36) Complete the following reactions. If no reaction occurs, write NO REACTION. O H3C CH2 CH2 C H Chemistry 1152 A. 2 Name________________________ H+ CH3OH + B. The “Product” of “A” + CH3CH2CH2CH2CH2OH O + C. H C NH 3 3 Δ + H3C CH2 CH2 C O O D. _ KMnO4 H3C CH2 CH2 C H KMnO4 E. O O F. H3C C NH CH3 + H2O OH CH CH3 G. NaOH H. CH3NH2 + CH3CH2CH2Cl O I.&J. Δ + CH3NH2 H3C C OH O J.&K. H3C CH CH CH2 C H LiAlH4 H2 Pt You supply correct reactants and conditions Chemistry 1152 3 Name________________________ 5.(4) Cocaine that is snorted or injected is really the hydrochloride salt of cocaine which is readily soluble in mucous membranes or blood. This salt is shown here. Crack cocaine or crack is free base cocaine, the neutral amine, usually made by neutralizing the amine salt with NaOH. Create crack here by that reaction: CH3 + NH O C O H CH3 NaOH O O C H 6.(5) H3C N CH3 + R-Cl CH3 If the R group is a long alkyl group, of what use is this product? 7.(5) A lactam is a cyclic amide and can be formed by two functional groups reacting with themselves in the same molecule (much like glucose does). Do that reaction here for 5aminopentanoic acid. O H2C CH2 CH2 CH2 C NH2 OH Δ Chemistry 1152 4 8.(4) Draw the structure of: Name________________________ (NH2)-Cys·Asn·Met·Leu-(COOH) 9.(4) An unknown is either an amine or an amide. What simple chemical test can you perform to distinguish between these two possibilities? 10.(5) The structure of raffinose, a trisaccharide found in some plants, is shown here. If this molecule has an acetal linkage, draw an arrow that points to it. If it has a hemiacetal carbon, circle it. Would you expect this to be a reducing sugar? HO OH O H OH O OH O H OH OH OH O HO O HO OH OH 11.(10) Complete each of the following… A. Polysaccharide + H2O H+ Δ B. Polysaccharide + Tollen’s Reagent C. Amino Acids D. Proteins + H2O E. Amylopectin Synthesis Enzymes partial hydrolysis complete hydrolysis Chemistry 1152 5 Name________________________ Extra Credit #1. Formaldehyde (methanal) is useful for preserving biological specimens and embalming cadavers. It kills microorganisms by inactivating their proteins by reacting with their amine groups (-NH2). The reaction is a dehydration between the amine and the carbonyl group with the formationof a C=N double bond. Write the equation for this reaction with this simple amine, CH3-NH2. Extra Credit #2. Consider… A mosquito was heard to complain That a chemist had poisoned his brain The cause of his sorrow You should know by tomorrow Was para-dichlorodiphenyltrichloroethane. Write me an original poem about Chemistry for some extra points.