MidtermSummer2000

MidtermSummer2000 - .V‘...

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Unformatted text preview: .V‘ N‘W‘W‘rmmww—w—mwn—w—fiu .4 “CHEM 2354, Midterm Practice Exam, Summer on, Dr. Hogan Print your name _ ‘rint your TA's name 1. What is the proper disposal method for: a. a small volume of-ethyl alcohol? b. fragments of a broken beaker? c. some t—butyl chloride prepared from t-butyl alcohol? :1. a broken thermometer containing liquid mercury? e. a piece of used filter paper? 2. Match these chemicals or reagents with the one highest priority hazard associated with their laboratory use. _____Tollens Reagent ___ethyl alcohol a. carcinogenic __dichloromethane b. flammable _,__sodium hydroxide d. corrosive" _cyclohexene c. metabolic poison“ Whydraz‘me e. explosive _nitric acid ___ethyl acetate _liquid bromine “silver nitrate “* A metabolic poison acts by interfering with a vital biochemical function and is usually referred to in the laboratory as toxic. * A corrosive poison acts by destroying tissue. 1 CHEM 2364, Midterm Practice Exam, Summer 00, Dr. Hrfian Print your name 2%,. rint your TA's name 3. Group the solvents cyclohexane, toluene, acetone, methanol and water as: W 4. Think back to the experiment in which you prepared t-butyl chloride and as you review the procedure in your mind note all the possible hazards. In other words, make a comprehensive list of those hazards and anything which you might reasonably expect to go wrong. U \ ' CHEM 2‘364, Midterm Practice Exam, Summer 00, Dr. Hogan Print your name I rint your TA‘s name \— 5. a. Estimate the percent composition of compound B in the vapor above a solution of 75% B and 25% A. b. Estimate the boiling point of the liquid at 75% B and 25% A. 5 E s E E E E g NOTE: Use a straight edge of some kind and make your estimates as accurate as you can. . Temp. 100 75 50 25 0 SB A CHEM 2364, Midterm Practice Exam, Summer 00, Dr. Hogan \ Print your name -V'rint your TA's name 6. You are using normathm TLC to follow the formation of t-butyl chloride from t—butyl alcohol. You have prepared four TLC plates, a standard plate (labelled “standard” and three plates from samples taken at various time intervals during the reaction (labelled "1", "2”, and "3"). However, you have lost track of which spot on your standard plate is t-butyl chloride and which is t-butyl alcohol and also you have forgotten the order in which you made the three reaction plates. a. Think about the relative polarities of t-butyl alcohol andt-butyl chloride and label the spots on the standard plate in the boxes provided. - b. Figure out which reaction plate was run first (ie. at the beginning of the reaction), which was run second (ie. later in the course of the reaction), and which plate was run last. Put the plate numbers in the correct sequence in the spaces provided at the bottom of this page. E F solvent front start standard 3 Number below firstreaction plate: VVumber below second reaction plate: Number below last reaction plate: I CHEM 2364, Midterm Practice Exam, Summer 00, Dr. Hckan Print your name ,rint your TA's name V 7. You are in the process of carrying out a slow chemical reaction which converts compound A into compound C. After running the reaction for several hours you inject a small quantity of your reaction mixture into an HPLC and observe three i peaks. You suspect that the three peaks correspond to reactant A, product C and an intermediate (B). Describe how you would go about figuring out which of the three peaks you observe in your HPLC trace is due to the presence of intermediate B in your reaction mixture. Assume that you do _n_o_t haye authentic samples of compounds A or C. cxmatmmwwmwmflmvwn«martini-man ‘fflMlIK.."!F'fl.“L“ l Ill‘xh-lar-‘t ' “- ' mmfitflfimwmmmmmomma-IrwinWW I \ . \ CHEM 2364, Midterm Practice Exam, Summer 00, Dr. Hogan Print your nmeM arm-int your TA's name 8. Describe how you would separate five grams of a mixture of the following two compounds into its pure components: : .CFgCONHa Cl-EC "NH:z N02 NO: : 5;: ‘3'» PA 9‘“?‘4“WLW‘MHWPWT‘"‘JP‘T‘ZR‘:l‘lj11- .‘ F1" u" mm W A a «- J‘f‘? ‘ “FL -.WWWW§1WWMAmmEnirflryycf I CHEM 2364, Midterm Practice Exam, Summer 00, Dr. Hogan Print your name Print your TA's name "__r 9. a. What is the order of decreasing acidity of these acids? (strongest first) 0.. 0H W G . Harm, cn3coon , CH30H I: E A B C D E a. ECADB ELDECBA C.EDBCA CLBDACE e. DEBCA b. What is the order of decreasing basicity of these bases? (strongest N o. 1) NH: NHQ NH2 0 4, _, a 5 N6. NH 2 ' N03 A B C D E a.BAEDC b.ABDCE c.BACDE d.'DBEAC e. BADCE \ \ CHEM 2364, Midterm Practice Exam, Sufiuner 00, Dr. Hogan Print your name ' M'rint your TA's name 10. a. Draw the structure of the product of the following reaction: M A A‘r—I-Im-W—mmnmulnarnlmmn b. Show the reaction which produces the product shown below. 02H 7 ————- 02H % é CHEM 2364, Midterm\Practice Exam, Summer 00, Dr. Hogan l . ‘L \ l l Print your name .‘flrint your TA's name 11. Calculate the theoretical yield in grams and the percent actual yield of t-butylchloride using the data below. Show your work! 7 (EH3 : (EH3 CHa-C —0H + H01 _"‘_*" CHs-(l: -Cl + H20 (EH3 (Excess! CH3 94.0 ml 55.0 ml (density 0.789) (density 0.842) _ 'K‘?'I‘N-klmlii‘vibWWW-NEW:flfi:§"iT-1-';I'fl.I‘.‘“fin-"mp. -_m_n-.m u n w-zu mummflmmu WWI-WMWHWEEWWT«TW‘WWQTwe“ CHEM 2364, Midterm Practice Exam, Summer 00, Dr. Hogan \ Print your name -.v,.‘rint your TA's name 12. You have three samples to identify. You know they are benzaldehyde, benzyl . alcohol and methyl benzoate,(benzyl chloride, (cldoromethylcyclohexane and chlorobenzene) but you don't know which is which. Devise a Mel scheme to differentiate the three samples. (use no more than 2 qual. tests) 0% Us 00 I: Benzyl chlon‘de (Chlommethylkyctohexane Chlombenzene E E a E i a 5 = E E g E E s 10 I \ " CHEM 2364, Midterm Practice Exam, Sun-miter 00, Dr. Hogan Print your name 1V rint your TA's name 13. What qualitative analytical test(s) would give positive results with these molecules? If no test would be positive write "none". H ‘3“ 2 5 CH3 b—CH—cng / CI no: CH3 —&l2—('3/ NHzH F 0H cH=o Cf CH; 11 CHEM 2364, Midterm Practice Exam, Summer 00, Dr. Hogan Print your name - 1UPrint your TA's name 14. a. Draw a detailed mechanism of the reaction between t-butyl chloride and alcoholic silver nitrate solution. List the important features influencing reactions which undergo this kind of mechanism. CH3 \ “1““(2 —— 0 CH3 , CH3 qwmmllwmm‘wutm]:Wmm-mmxn m.m:r..x.s.w'uwns um" "m" “c” b. Draw a detailed mechanism of the reaction between chloroethane and a solution of sodium iodide dissolved in acetone. List the important features - influencing reactions which undergo this kind of mechanism. CH3 \ “13C _ G W H E E E: E E E g i 12 CHEM 2364, Midterm Practice Exam, Summer 00, Dr. Hogan Print your name frint your TA‘s name 15. Compound A, C7H140, gives a negative Jones test and a fast positive Lucas test. Compound A reacts with the Lucas reagent to give compound B, C7H13Cl. Compound B gives a fast positive alcoholic silver nitrate test. Sodium iodide/ acetone reagent does not give a positive test with compound B, even after several hours. Compound B can be dehydrohalogenated with base under E1 reaction conditions to yield alkene C, C7H12. Compound C reactswith Brz in carbon tetrachloride to give a dibromide with two chiral carbons. Further dehydrogenation of C yields toluene. Draw plausible structures for A, B and C. _»_ a: E, s '5 15. 5 e . E" v . "‘"‘WTBH‘W'F'V‘EF‘WIWWVS"*RWWMWIWFWVWW".rams-“(5111 MW“ 13 \ \ CHEM 2364, Midterm Practice ExAm, Summer 00, Dr. Hogan Print your name tint your TA's name 16. Propose a two step synthesis for compound B starting with compound A and any commercially available reagents. ‘- COOH _———.I —-————'I .COOH CH3 A . nu‘mmnrfi‘pplrxvuf; I;." 3;?“ "‘r1"-C,'l.‘“3"1_'."“-‘:'.“'Fluid-L‘me “ V f‘“ "A‘WWWWW E E E. H 14 ...
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