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MidtermFall1996

MidtermFall1996 - "Esau 2354 Midterm Exam 9 Dr...

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Unformatted text preview: "Esau 2354 Midterm Exam: 9 10/8/96 Dr. Weingarten Print your name-_....._...______...__._____...__....__._.;_.__.-__ Print your TA's name ______ ____.________________________. C W); . U 1. What is the proper disposal method for: a. Filter paper contaminated with acetanilide. b. A small quantity (10 ml) of concentrated HCI. c. A t'orn lab cloth d. 10ml of dichloromethane containing dissolved acetaminophen. e. All the fragments of a broken thermometer 2. Match these chemicals with the one hazard most likely to be associated with their laboratory use. ___acetic acid a. carcinogenic ___isopropanol b. flammable ___nitric acid c. metabolic poison * _.__iodine d. corrosive ** __._.p-nitroaniline ___toluene ___hydrazine ___potassium hydroxide ___bromine ___hexane ég 3* A metabolic poison acts by interfering with a vital biochemical function and is git? usually referred to in the laboratory as toxic. - ** A corrosive poison acts by destroying tissue. gamma; CHEM 2364 Midterm Exam 10/8/96 Dr. Weingarten Print your name _____________________ ___._ ““““ __ Print your TA's name... _______ ___._______._.___..______._ V} 3. Group the solvents acetone, ethyi ether, methylene chloride, acetic acid, cyciohexane and methanol as: 9.01% in rm i V n - l r 4. You have just begun swirling the reaction mixture containing t-butyl alcohol and hydrochloric acid when the stepper pops off and sprays some of the contents on your hands. a. What is your best course of action? b. Your lab partner suggests you wash your hands with sodium hydroxide solution to neutralize the acid. What do you think of this idea? .V. CHEM 2364 Midterrn'Exam 10/8196 Dr. Weingarten Print your name_____.________.._ _______ _.___......___._______.. .‘rint your TA's name___ \\-—'r' > 5. You have recently prepared t-butyl chloride from t-butanol in the laboratory. a. Describe the laboratory procedure (technique not theory) you followed to synthesize (make) the t-butyl chloride. b. Describe the labOratory procedure (technique not theory) you followed to isolate (purify) the t-butyl chloride. c. What data did you generate to confirm your identification (characterization) of the t-butyl chloride product? Calif! 2364 Midterm Exam 10/8/96 Dr. Weingarten Print your name ___________________________ ..._ Print your TA's name_.______________.____.___.__..____.___ ““ 6. You are using HPLC to follow the formation of p-nitroacetanilide from acetanilide. You have prepared four HPLC traces, a standard and three traces from samples taken at various time intervals dUring the reaction. a. Place the three traces, A, B and C in the correct time sequence, first, second and third. pcni troucetoni l i as ocetanilide standard A B b. Circle the by-product peak which appears along with the p-nitroacetanilide and suggest the most likely identity of this by-product. 5 . L33. ‘9, E ,7. -': a; V g- “rumpus? “'Y‘N‘V‘WWWin"Hfl’i‘liflw‘q'w‘?:i13"‘S‘W'l‘fifi‘l“www.mWWWIWMW-W“TY:l .‘vwrm cm 2354 Midterm Exam WIS/96 Dr. Weingarten Print your name ___________ ____ _______ ___ _____ _. Print your TA's name,___. ———-———_————-I——— V 7. a. Estimate the composition of compound 8 in the vapor above a soiution of 85% A and 15% B. b. Estimate the boiling point of the liquid at 85% A and 15% 8. NOTE: Use a straight edge of some kind and make your estimates as accurate as you can. Temp. 100_7s so 25 0 so "'Ci-iE-M 2364 Midterm Exam 10/8/96 Dr. Weinarten Print your name__.___________...________....__..__.._..._.._.___._ Print your TA's name_____.__ ____ ...___._ _____ ___.____ V‘ 8. You are given three unknowns A, B and C which yielded the following test results in the Qualitative Analysis of FunCtionaI Groups (P-positive, N- negative). Which of the seven molecules drawn below the test grid are A, B and C? Circle and label your answers. Nal 5 E. "CHEM 2364 Midterm Exam 10/8/96 Dr. Weingarten Print your name ____________________________ _._ Print your TA's name __________ ___._.__________.._.______ 5 V 9. What qualitative analytical test(s) would give positive results with these molecules? 3. 0' b. 0” 013 c. CH: d 0 0“ clIh‘CHZCHZEH / CH: a CHEM 2364 Midterm Exam 10/8/96 Dr. Weingarten Print your name ____________________________ __ Print your TA's name__.._____ 10. Describe how you would separate five grams of a mixture of the following two compounds into its pure components: OCHchOI-l OmzdhOH N02 N02 V ‘ CHEM 2364 1 0/8/96 Dr. Weingarten Midterm Exam Print your name ___________________________ __ Print your TA's name...____..____ _-_—_--___—_—_-_— .— 11. 3. Give the IUPAC name for the following structure: 2 9" / _°”.‘°”=‘ CH3 "(EH "? Br H b. Draw the structure which matches the name: N.2.4-trimethylaniline. VJWHTF'IWWNTJRTEW' L\J'_'_‘\ .T‘;"':-"._"'\‘ TNT“ HM‘IWI'EK‘“ 112‘} 3?? .‘(fi-‘mIn-vwm'm: ‘ngs :"M‘ V'KL'IWH '" '; :nmn'v-fiwm' : WWWHW‘W'TQWJLHW‘H'HW . ‘T'VNr‘mmr; l «a CHEM 2364 10/8/96 Dr. Weingarten Midterm Exam Print your name___-__.___._________________.________.___._ , Print your TA's name_________.______.___.__.__ "’" 12. (1.) Calculate the theoretical yield of cyclohexene in grams and (2.) the new actual yield of cyclohexene using the data below. Show your work! HO . 0 fl 0 + up A 55.5 ml (density 0.81 1) 82.2 ml (density 0.963) 10 CHEM 2364 ‘ Midterm Exam 10/8/96 Dr. Weingarten Print your name._______.___._._______.___.._.__..__________.__.- VV' 13. a. What is the order of decreasing basicity of these bases? (strongest No. 1) A. NH3 3_ NINHE ‘ a.ABDEC NHCOCH; ' b. BADEC C. c.8AEDC NH; d. BACDE D. e. CBADE ' Mt 5- 0 a “maven-MWWW'rummwmummumu1::-mzr..i‘g‘;:g\. My; . H mm ‘.\‘.;‘-...-h.\.m - w n A E b. Predict the mag; product(s) of mononitration of: E o coon O'é'CH’ 2 0H 2 CH3 5 5 0: Br c-d i as E g, 11 \...’ _ Print your TA's name_______._____. CHEM 2364 Midterm Exam 10/8/96 Dr. Weingarten Print your name___._ _____ _________.._.._._-_..___.....___._... Propose a synthesis for 3-aminobenzoic acid starting with toluene and any common reagents. 14. 12 g CHEM 2364 Midterm Exam 10/8/96 Dr. Weingarten E Print your name__..__..______..______.______.___.._.______.._ Print your TA's name____ _—_————.—-————— "~' 15. Compound A. C1oH140, a chiral compound, gives a positive Jones test and a negative Lucas test. Compound B. CroHnO. (also chiral) forms as a re5ult of the “ Jones test and B gives a positive Tollens test. Compound 8 can be further reacted with the Jones reagent to form compound C. C1oH1202 (also chiral). Compound C can be oxidized by permanganate to terephthalic acid. Draw the structures of A, B. and C. HOOC ©0001 Terephthalic acid 13 .\ iMWW’TFJTFF‘nwwmmmn‘mir‘ww\Wxmqwrtlzwmv-mmuumrmwmwnm (Wm [7-3 t'i.‘"‘1.".“R| many-1. m E 2 i i i . E E CHEM 2364 10/8/96 Dr. Weingarten Midterm Exam Print your name _________________________ __._._..___... Print your TA's name_______________,__._____.___. 16. 4———_—- Y0u have prepared a sample of cyclohexene by the dehydration of cyclohexanol. HPLC analysis shows an impurity in your sample, which a mass spectral analysis indicates has a molecular weight of 182. Draw the structure of the impurity and suggest a plausible mechanism (including proton transfers) for its formation. 14 CHEM 2364 Midterm Exam 10/8/96 Dr. Weingarten Print your name________________________________________ r , Print your TA's name _____ _________________________________ “" BONUS QUESTION 17. (a) Explain with words and drawings. on a molecular level. the difference between a normal phase and a reverse phase chromatography column. 1H‘ilW‘V‘ifl‘lWflW‘l-iUmn-vfi'_“."-1l-w‘f-‘f-il-anx.ll - . a ‘l.i"“““" (b) explain with words and drawings, on a molecular level. how you might transform a normal phase silica gel to a reveae phase silica gel. “4‘? 'fl l‘l‘lMWlWWWMWEWF‘W .’.‘. 15 ...
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