MidtermFall1997Key

MidtermFall1997Key - CHEM 2364 Midterm Exam 10/6/97 Dr....

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Unformatted text preview: CHEM 2364 Midterm Exam 10/6/97 Dr. Weingarten 1V .‘rint your n_ame_....________________-___7%éé2’£2é__éE/Z__ Print your TA's name_-____._____________._ _____ __.____._ 1. What is the proper disposal method for: a. 10ml 10% H3P04 solution lit/ugh (fa-um oft/3.1»; Wflg [(319 5’0 L413 - b. all parts of a brol<en thermometer (“of/gal. .3 9/345 94461 Ala—a”: ire. :1- 4:0 Qmwmnic‘x gig—«(1W . Dus1L yrs—e- rut-114i M l younger? solar c. 15ml of 50/50 methanol/methylene chloride solution fawr [UL-L) aw. LuESj—e £o#/e. . . . L'. 3.- E fi; lif'ut'oq d. a pair of torn rubber gloves yo [face “A OWE/Pr E.- =; F. E- E. E E E {D caatéf LLIJSL e. a 59 sample of acetylsalicylic acid f [Ace iv} bueko‘ll’a Match these chemicals or reagents with the one hazard most likely to be associated with their laboratory use. 2 $6 _QLnitric acid a. carcinogenic \(B. _b_acetone b. flammable dfiLaniline r c. metabolic poison * .d___iodine ** _b_styrene 5%_Lucas reagent Ckg'..hydrazine potassium hydroxide _ Echloroform _€_—_Tollens reagent d. corrosive e. explosive \ . . _ * A metabolic poison acts by interfering with a vital biochemical function and is usually referred to in the laboratory as toxic. 1 ** A corrosive poison acts by destroying tissue. CHEM 2364 Midterm Exam 10/6/97 Dr. Weingarten ‘rint your name______.________...____..____..__.__._____.______ ‘V Hrint your TA's name___ _——_———-———.-—————-._———_-—q—— 3. Group the solvents isopropyl methyl ketone, diethyl ether, methylene chloride, propionic acid, hexane and methanol as: polar - intermediate non-polar @yoptwcc. 8.0-9? Emmy-l {claw r. Just as you are about to attach the reaction flask to the bottom of the Vigreux ' column in the cyclohexene synthesis experiment it slips out of your hand and falls on the bench top spilling some of its contents on your hands and arms. (a) What is the composition of the reaction solution? (b) What is your best course of action? W %'Z [L39 W, ’5 LJLfiJ—T 0" 15.6 4:91;) 920.1 .5. 'l/UASL your" WW9 0M7} LOU/“(A {swa 010 wit/31w. . . , - Dos-(- Mahler l/LDLM MALCO; Le Whahze QM. v Mm; back 15a? Mm all/MM!) ClmflaJ rims: @521" We,“ WLKK £13 002M. NaLl-Ff VW TA afl— {’44 acct'cb-ul‘f. "BMW . CHEM 2364 Midterm Exam 10/6/97 Dr. Weingarten firint your name________..___..._._.__.___.._______.____.___.__.____ Verint your TA's name.___.__..____ 5. ——_u——————_n¢-————.——.m- 3. Estimate the percent composition of compound B in the vapor above a solution of 60% A and 40% B. ‘D F b_. Estimate the bofling point of the liquid at 60% A and 40% B. Temp. 50 $88 100 75 You are using HPLC to follow the formation 0 p-nltroace am: e acetanilide You have prepared four HPLC traces, a standard of reactant and product plus three traces from samples taken in the time sequence indicated. However you have lost track of which peak is which in your standard. Use the three time traces to determine the identity of peak A and B in your standard. fl 0 0 standard fir“ Sample second sample iast sampie Ari-[S fi’NLLVv‘a—(etwsllfit’é’ Q-‘VS 'ECQ—Lawnhril CHEM 2364 Midterm Exam 10/6/97 Dr. Weingarten Mirint your name __________________________ __..___.-.____.__ Print your TA‘S name_.__..___.____.._____.___.___.___________.___ 7. Describe'how you would separate five grams of a mixture of the following two compounds into its pure components: \V \f\ ‘0 g ‘. 8 gr 9: 31’ g I 33 ‘ ‘ M DC)“ pcM A"? M] \ ‘- ChLC"; (“Z-71,34,050; a \7 c I / @‘prufav-WMSOL: Q) “Mahalaka £333 l®euz4mkflfi [L A7, 42,52 4'- DCM ' (PK-1 93% A7 499?» boot / \ we t;th flflww‘é on?!" W br\ W CH . IU~Q CWLL “Dr W7 +045ij Lime/wits bcM I CHEM 2364 Midterm Exam '- 10/6/97 Dr. Weingarten °rint your name_______..____._ ________ ...__ ________ ______. verint your TA's name__.._______________.____..______.______ Place these benzene derivatives in order of decreasing ease of nitration (most easily nitrated No. 1) 109‘ / A ignore F i 1 ‘ 9. What is the order of decreasing acidity of these acids? (strongest No. 1) a. DCBEA ‘ b. CDBEA c. DEBCA d. ECDBA e. DAECB /0er$ wk 7—1915 O O WIS! I ‘CHEM L7, int (rint 10. w Midterm Exam Dr. Weingarten 2364 ——_-n-_———-————_——————_——— your name__.__.__.___..__...__.. your TA's name _____ ._._._____.____.__.______.__.___._ _— Give the IUPAC name for the following structure: ignore Draw the correct structure for 2,5-dibromo-3-nitroaniline. igno r6 WW“ 1'; m. CHEM 2364 Midterm Exam 10/6/97 ; Dr. Weingarten V Print your name________._______.._____._.__.______________ Print your TA's name________._______________.._______._____ 12. Calculate the theoretical yield (in grams) and the percent actual yield of acetanilide using the data below. Showyour work! W NH2 . NHCOCH; + CHsOO‘0 ——-—r + CHaOOOH cr-rsoo’ ‘ 30.6 ml excess 30.2 g (d = 1.022) (actual yield) ,1,th A9}.— C9’ (1‘60? Q" 720‘” Hq= €1.07; 14-,1 106'; p» mm 3;» ILLOI 0“ “0‘00 Mr .— - qyllc [36-1597— __..__- r . l 9» ., 31.17 a F l . r 1m: 3:3.kav[Olly/u3 jv {Lemuel { y'eu._03%x I35 c 45:4 ,s n r CHEM 2364 Midterm Exam 10/6/97 Dr. Weingarten Print your name_.____________._.___._____..___..___;___..___ "d’ Print your TA's name_________________.___._______.._____. 13. What qualitative analytical test(s) would give positive results with these . molecules?_ We a? - / COCHa ‘ OH Peck, I‘M EFL/CC!” st a. CH20H3 ° 2H‘DM? CH20H Jams BrL/CC/v 14. You are given three unknowns A, B and C which yielded the following test results in the Qualitative Analysis of Functional Groups (P-positive, N- I negative). Which of the seven molecules drawn below the test grid are A, B and C? Circle and label your answers. CHEM 2364 Midterm Exam 10/6/97 Dr. Weingarten Vi rint your name____.____._._..__..___.___....__..___._______._____.. Print your TA‘s name____.__.__..___.__._____._____. ____._ 15. Qompggnd A, C10H140, a chiral compound, ' C1oH120 (also chiral), which forms as a result positive Lucas test. Compound 8, / K9 of the Jones test with A, gives a negative Tollens test. Compound B, however, Q/L’P gives a positive 2,4-DNP test. Compound 8 can be oxidized by permanganate to benzoic acid. Draw the structures of A, and B and indicate which carbon(s) are possible stereocenters. COOH O benzoic acid if? chi;- A if. it" "'5 SSW-OS B L:— }—0£ c —C. e. i ; _____.:- W; l l u on» i H‘ 0 / \7 L ,Toflwf CA 4— u s +1’q_DM, )k INA;ng SWI‘C CJ-‘MA-{D’Y' CHEM 2364 Midterm Exam 10/6/97 Dr. Weingarten V'rint your name;_..___...._._-___.___.___..__._..____________.___. Print your TA's name_.__..___._.___.___________..____________ 16. Draw an arrow pushing mechanism of the formation of acetanilide from aniline and acetic anhvdride showing all intermediates, proton transfers and products. 9 no re 10 i E E E i i E F F i Midterm Exam 10/6/97 Dr. Weingarten 'CHEM 2364 ‘ “tint your name ______ __. ___________ _.__..___..._____..___. ‘i'rint your TA's name___.__..__ _____._______.____________ Propose a synthesis for 3-bromobenzoic acid starting with toluene and any common reagents. 17. 5mm 11 ...
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MidtermFall1997Key - CHEM 2364 Midterm Exam 10/6/97 Dr....

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