322bs09_plq2_2_key

322bs09_plq2_2_key - CHEMISTRY want/5’25 W08 We 3 fr...

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Unformatted text preview: CHEMISTRY want/5’25}, W08 We 3 . fr fl',fi T.A. 4. [(9) . .. ,r' I g \ This test comprises this page and TOTAL gig) five numbered pages, including a graph. Lab Quizze- wi 1 be available -t lab ch; k—tut and ffi fice 5' ‘ hou 8; Tu a.m.' ab leets at 9:30. =-ginning;Fri 'ec 5,§qui zes will be avail.-le a3 SGM 103;§or if ou initfial h:re .' ! yo quiz wil; be p out in éhe st oy roomq SGM 02, Fri a m., Dec-5. All u claim:- tests wfll be thrown dut Ja: l9, éoofi. . f I , if ; ‘ i ,5: g 1 s: -1- 1. (6) Recall that aniline, Ph—NH 2, was converted to p~nitroaniline (PNA) via acetanilide, Ph—NH—Ac, and p—OZN—C6H4-NH-Ac. (a)(2) Ph—NH—Ac was made from aq Ph-NH swirling, than adding aq NaOAc. product with some unreacted Ph—NH Answer THIS question only—~ 3C3by adding excess A020, Adding NaOAc fiizfll gives 2. Explain in <20 words. possible NET negative otherwise. M ___5 [51% mi/I’M'OQLU‘CA («of/L tell why one did n9; heat it (i)(2) 38% ("cone") aq HCl; ii)(2) aq NaOH. Use <247words total. A 69f HG a4 Wm}? «24» CW w ¢ «7, (b)(4) To hydrolyze p~nitroacetanilide, under reflux it with either: or 2. (4)(a)(2) 2aNaphthol (HA)'s pKa = 10. Its anion, A‘, reacts 2:11 much faster than does RA in coupling with Ar—N=N+. With a relaxant chemical equation and <15 words, explain why the reaction gets signer as pH goes from ~12 a 14. flji3/0 3. (10) This question deals with the formation of glucosazone (GPO) and its cyclization to a l,2,3~triazole. (a)(4) Balance the chemical equation below. Include correct coeffi- cients for the other aiming material andthmother productS- ‘/€4(£(M0’2, NNHC‘H, 0 “t $==O H JE?-—n-—: CHOH NNHC‘H, (C'HOH), +. (CHOH), + F4 + + (Egon imoim (b)(6) The overall scheme for GPO -———+p triazole is shown below: Dissolution Step 1 Step 2 k - k k d(1ssoln) ___;_’_ 2 giving a deep red color which then disappeared. This by itself does not prove that Cuso4 is catalytic nor that the red species is an InterMediate for the Product. Using <20 words, propose a way to test whether CuSO4 is in fact catalytic, keeping in mind what a catalyst is fan Maegan wrflt um 0&6 1 'fieC \ {area am and. (ii)(3) Treatment of the rxn soln with charcoal did not remove the green color. But one got cleaner solid than would have pre- cipitated otherwise. Describe the visible change in the solution and tell what was removed, in <15 words. Zero for tautology, e.g., "color change" and/or "impurities" “(a ———9 elm arm. a; m) em, Jy‘pwz‘ww (1) anhydrous a (55° — i.e., 10 9 glucose (anhydrous) 8 (> 98°). glucose W. calculations, solid, 5 and/or showing state (1) the composition and amount of each and (2) the amount of each anomer in solution. M Ja/(‘g/ (avg/«4) (A. [wkyflfi 3 “ME wk (415‘ A26, QCMW WI (J/K, M“; flf€€,/Wd 7/ (awe W MafflgulmC/fi “of a (3) A lo-mL filtered portion of the GPA reaction mixture stands 7.5 cm high i I \ he polarimeter tube; it has an observed ( rotation, a = 15° After adding 1 mL conc H 80 , a . -°Sd. , . _ 2 4 obsd rises t. The spec1f1c rotation of a—GPA = +100°; take that of 13- " = 0°. Assuming the final GPA mixture is and 10% E, calculate the percentage s-GPA before adding ‘ - acid. Full credit onlx for minimum gath calculation. M \ 0" {d/w 3 K 4-4 M4 600 #4 87 :30 «Lu 70%‘6 (b)(3) The mp’s for the GPAs are 134° for 3, 112° for a. A student gets 130°-132° for B, 105°~110° for a, and a mixt mp of equal amounts = 85° — 92° Assuming the B is >95% pure, \ 6. 4‘ it"? The mutarotation of glucose, viewed as either shame: a Ln: equilibrium mixture; is a first—order reaction, i e., the reaction rate = a constant times the cone of the starting material: —d[A]/dt k[A], where t is the elapsed time and k is the rate constant. The solution to this differential equation is 1n([A]/[A]0) ~kt; the — sign means k is posi- tive since [A] is negative. In such a process, [Al's Lela; Live rate of change is constant, e g., if 20% reacts in 1 min, then 20% of what remains reacts in the next minute. The half— time (or half—life), t”, is the time required for [A] a %[A]. (6) Refer to the following page-- plot of optical rotation data vertical axis, is detach it if you wish——a semi-log vs time for a-glucose. For the 0 refers to measured rotations. The solid line (a~aeq) vs time, the dashed curve is just a vs time. Tell in <8 words. Mm vw rah/rm. (b)(2) From the graph, the half—life for this process is ~18 minutes. Using the bold-face formula above, calculate k, constant, including units. Ash-11c y. a 15%. %_ (c)(2) It is important to get an accurate rotation for um mixture. Given the t%, done to get this rotation data, and why did it work? Answer in <1 4W4 /H‘//(¢/LU3 Calculate its solubili— 64% B and 36% a. 3 in tap 16 I *ll, 1 00 :5; 2' 3" (9 a“: ‘60 q {u I as H 4.-__._—_..._—__._ ——_-———...——.—..—.—.__.———-———.———..——_.——_._._ _.:'-—_—_——_.——. ——.—-—-—_o——_————_—-n_.._____—_.—.-——_——.__ __-—__—__-——._—..__-__._———-—._—u—._—__—._————__..__ — ——.—_——_———.—_—n———-——_——_—_-——_ g.._ —..—._————. .——.-—__—__——————-——_——__—-—~—__—__ ~—....—-—.—-—-—_. —u_-—__—————_——_———__—__—._———-—.— x _. —————-———-——— —_——_——_—_——_————_——-—_———_. — _—-—-—_.—_——._ . —_-—.—_-——.-——.————-—_—.——_~—————_ a...—_ . —-——_-————_—— ——_—————_———_——_——————.——_—_— ._...._...'..’. —_...___——___. ._.-_____..._——_.—__.____._-——-——_-___ __ .. ————_—_—__—_——_——-———.——a——_—————_——_ n._ .. -——.——.——_.—— _———-————-—_————_—_————— —_fi_ fifinu ——*— ——_-—-—_———.——_. ——_-——————_———_—_.——.———.u——_ —_ *—“- fifih“__fifi . . ————_-——.——_- ———_———..—-——_——--—-__—_—_. —- _*—_—— —*—*m*__* -_—- _fl—__ —_—~I%——_—h_ -——__ .—-—-—a——u—_-——_-u— ——_——-—_————_—————-————-—_ - ——————-...-—.——_ —_———-——_.——_-————_——_ n. —_*“I——' _—_—-—_m—_ .m-— —_——HI_ __-~-____*_ *_—-u_ —***-m_—* _*—m_ __*—_—_“h —“IH_ ' “m_—____—— —— Im—_“C-n--—s_—I—_--q—"n_-_—_“ nun—u.“ uu—II—D-I—‘n-‘nb-m—j- _—-.-m---_—_—-— uc—nuI—u Inn-m—in—u—nq—mal-Im. Incum-uwg—n———_— “II-m. I-m—o—mmml—un .- -- "-"u_--m-—I_ smug—I'- I“-_‘__-—_u-*mm --—.—————-————- Hun..."- .- _-“--——- m—u—m-u-g “mu-——-— I . I—om-u-nDn-m nun—m “num”———n—_ I—"m —l “mumflmm—uI—uuqm nun-'u_-—-_ In“. II I. I—II-Im—mI-“_wumum 'Im-I_—fl-— u-__.— -mm*_—m Int-nu... p—_—n_u-_—-— “I—I— -___u—.——-——c-I “an __— I'mqu Im-I _-—--III IIII-III" -——I_ —.I—--- I—I'I-I ——II—III—-- “In-I..- _-—— “IIHH 'mI-u fi—I-IIMIIIIIfl-Im m—fi— _--_— _— "I...qu _I—-— —u-——ll-— "- _I_-—- n-‘--“._.__ _—II—. —II "I “III- II-IIIIIII InI—— ._—-I_ II — “II—- III "III—— __III_I I maII‘IIIIIIIIIIIIII-III-__ _—_I-' III-“IIIIIWI—I.“ I_--IIII__I_ "h— ‘ '_' a “‘ -—_.._-—= —" "“ --—.-._--—.-—__. _ -“ — — _" '—_"' —...._ .—..._..._- —- .. —_.—._._._-——..._—-._..__.___.,_,__.._—-___..._-.——.—.__ -.._.._ _.._._...._.. -___.__.______.——-_.._-—.__.._._..__....._ __.—__—._.._..._-___-.._ _.--—__—.—.__._—._-—__.-_—____-___..._._.-—_-__—_——_.._ _..__-—._._.-__..___. ..:—____.__.=...-——....————.... _.-__...___.._-——_.._..-—_._——.-—__._ _—'_._—.... "_' —' _' "' 1*...— "— _—-_.._"'" ' '_'_ ' --_._ _—-.._"" _""__— —-——.__' — __ - ———_ " .___.__._-—_._-..__.__ -_..._.._—____-____——_.-——...__.____._..___—.—_.—-—.._—_.___ - —-—.—-_._—_....._—-__.. -_._.—._-—_._.—_._—___—.._.._-_.__...—__.—.-._—_.._ __—.—-.-.._-—._—-.—...-.. -_._--——-__—_-—.-_—-—-—.__-_.__-__..__——_—_—.—.-—_— ——_—-.._——-—.-_-.—- nun—.u. —-——.—-—._..-—-——__—-.._—...—__.._——-_-———-——_ .——_——.._—..—_--_—— —_—a—u-—______.___-___...._ .—._-.-_...._-—._.._ ——.—__-u_-—_..._ -.-__— -—_...——__o—__--—_.__—.__——_—————__ -——_-—_._——_-—.—-— .—-——-.-—_-—_-—-_—.___——_.——_—_ ——_.-——_.-—__——_= —:————-—--—_—--——_-——.—_——-—- ~—__—-——..._— _ _.._.....___ —~—-—— —.-*.-_—--—__I—_ ——-———._——.——._ ——_——~———.—_——_—__ ———_—-—.—_—_—-——.._ —-—._—_—_—————.—n—— ——_—___—.—. —-—_-———_—-——-———_—_——_—— ——_-..-—u_- ——_..--——-————_——._-—_ —_--——---—_- -—_ - —_...——.—-_———.--—__————_ _—__I-—. I “—*—__-H—I——__—- ——~-—H—- I_IIH-_m-—**_-_m-_- _-_I-I-_I- “Q-““~—-—-----—w“ —_“I_ maum____—---_u_-—— Ifl—ID—“I ——-—-—-—----—-fi—--———-——n—-———— ** m——*———-*-_—-—— m_-_ __—--I———‘_“—HII*- m-“IIMIfi- _-_-_*_-—-I_-* .m— tong-nun“. “ own-“-mH_—--—__—- “fi-Ifi-In—II u"_————_—-—-———___——— HuI-II—ul— m-.-—“—_’——-——u_ _—-—-—-I---II-- Inn— “gnu—I—m—u—I-p—n—“m- *—_‘-Iflnu_ -————_-—_-—n—-—-—_- ——-—_—-—._ -——_-——.——_——— —*—_—n—n-—nl _—-——__——— _——u——-*_ -———__“I—_—- ——_“~-- -———-——_— _—_-_—m I———__——= ——-_I*—_ —_—__—_ _-—*___ _——*_——— _“——I-_Iu ___—-_I_I ____——— —___*I—-I —-—~————— ———-—__I- __—__—_— —_—_I__ '————_—_— ——————— _—_—_——— ——_———_ -—~____— —-_——-—_ I——_—__= ——__—In—_ I—“_—_ *——__-—_w——————_ _—__ _-—_ _ __—_— ——__—_— ——_——_— ———__——I _—_—__— —_—___L\ m——__— ——_—___m___——__ ——__-—_- -—_____ “III-IIIIIIIIII III“. I III-m"- I“ III-III:III:I “I'll-II III-I'll“. I I I I E II I I I I I E I I I. E .3- I=II :- ...
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This note was uploaded on 10/12/2009 for the course CHEM 322AL taught by Professor Jung during the Spring '07 term at USC.

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322bs09_plq2_2_key - CHEMISTRY want/5’25 W08 We 3 fr...

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