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FinalFall1996 - v"mum-WINNIN—...

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Unformatted text preview: v. "mum-WINNIN— If'nfi‘fitwyi-‘Kjfif-xnmwnrmrr‘Ir'rvu-nfl": h‘ - "A war IPNWF‘M‘H mmnmmmmmmmmwm wwwmwmmmwmym wwqmwwrnwmwzyfifmw “TWP-‘1 ’M‘JPW-TJEWN‘ m rm- ”9%” FINAL EXAM. CHEM 2364 student name__________________ 12/ 3/ 96 Dr. WEINGARTEN TA name _ 1. Describe the best method for separating gram quantities of the following mixtures into their pure components. CH3 --CH2 >CH- -OH - CH3 —CH2 o=c -CH2 NHcocua CH3 FINAL EXAM. CHEM 2364 student name 1 2/ 3/96 Dr. WEINGARTEN . TA name_______________ E 2. Describe the best method for separating gram quantities of the following mixtures into their pure components. E a. r CH2 ‘ CH3\ ’0 9‘0 9. E 0H 0 g E n o O \ ° ° minor amount FINAL EXAM, CHEM 2364 student name 1 2/3/ 9 6 Dr. WEINGARTEN TA name 3. Devise a scheme to differentiate the four 'unknowns' shown below using oniy gwg qualitative organic tests. 0: . é\—CH3 CHacl CI HzCHzCHgCI . CH3 (3-1:,ch3 CH2CH20H3 FINAL EXAM. CHEM 2364 student name 12/3/96 Dr. WEINGARTEN TA name 4. 3. Give the IUPAC name for the following structure: CHa-QHz 0 0Q: /&-O-CH3 1°=°\ H H b. Draw the structure of m-isopropylbenzoyl chloride finch-m“wlmwmtmfi'my“?umrmwmwmwrwumnwwwm 5 flaw-mm mwmnmmw ‘ _, _ ‘. FINAL EXAM, CHEM 2364 student name 1 2/ 3/ 9 6 Dr. WEINGARTEN TA name Fill in each square with a P indicating a positive test or an N indicating a ne-ative test. Nal Bra FeCI3 2. 4- DNP Toilens ethanol acetone CCI4 Jones com-aund- ‘1"! A Uni.‘F:I'xumww:mv"mwmwm\iasmLam-n-nI?'Ii.!‘...\-m';'v-w'i -r- I1\‘."‘1-'I|I.|\‘ ww-v» :- “'v‘w "V" “ ‘ “ FINAL EXAM, CHEM 2364 student name 1 2/ 3/ 96 Dr. WEINGARTEN TA name www.m- --- —-vu-m-uw-mm-n m 6. Match the NMR diagram with the correct molecular structure. A. ? CH3 "C'O "CHZCH; M l I - B. CH3 \ 3: ’CH; E] CH3; H .6 tic”: 0- Cl CH3 -CH2 —¢-CH2-CH3 I l I l Cl CH3 CH3 '¢'0 "CHa‘CHz -Br CH3 1 1 v5 gamma-m . IM-Wle-‘WFE‘N‘~V‘.‘“-“..~“.‘.“"-“‘.'1'”r ' I O g E a FINAL EXAM. CHEM 2364 student name 1 2/3/96 Dr. WEINGARTEN TA name 7. b. Sketch a reasonable proton NMR spectrum for the moIeCUle below and identify each resonance. /°“°\"‘ o o I L \QH E‘ 3 CH3 FINAL EXAM, CHEM 2364 ' student name 12/3/96 Dr. WEINGART EN TA name - 8. a. balance the equation 1). calculate the theoretical yield of the product (in grams) c. calculate the 12mm. actual yield of the product i d. circle the limiting reagent e. SHOW YOUR WORK! BOX AND LABEL YOUR ANSWERS! ‘2 o H O-C-CH20| + CICH2 3‘ ———-I- + HCI H Ci ClCHz-g-O 10.19 21.59 15.79 (actual yield) FINAL EXAM. CHEM 2364 student name I 2 I 3/ 9 6 Dr. WEINGARTEN TA name 9. a. Place these carbocations in order of decreasing stability (No. 1 most stable) CH3 0' CH3 H CH3 0+» CH» ~ cw 0e CH3 CH3 H CH3 A a ‘ c o E a. ABECD b. EABCD c. EABDC d. CDEAB e. EBADC b. Place these bases in order of decreasing basicity (strongest No. 1) O O O O 0 CH3 -CH2 —&\0 _ H-CH; -6\0 _ F-CH; «5‘0 _ crcna -CH2 45b _ ci-CH2 -&\0 _ A B C D E a. ABCDE b. DECAB c. ABDEC d. BADEC e. ABDCE FINAL EXAM. CHEM 2364 student name 1 2/ 3/96 Dr. WEINGARTEN TA name Propose a synthesis for acetaminophen (Tylenol) starting with aniline and any ' 10. common reagents. H 0 h‘é—CHs H0 10 E s ; FINAL EXAM, CHEM 2364 student name 1 23/ 96 Dr. WEINGARTEN TA name 11. Benzopinacol gives one product when catalyzed by acid and another pair of products when catalyzed by base. Draw complete arrow pushing mechanisms (including all proton transfers) for the W catalyzed pathways. C3 <2" 9H C BenzOpinacol 11 FINAL EXAM, CHEM 2364 student name 1 2/ 3/ 96 Dr. WEINGARTEN TA name ,_ 12. Propose a synthesis for the molecule drawn below using only starting materials from the list provided at the bottom of the page and readily available reagents. . target molecule . lflWfitfimfimmmfl'ufimmwm‘mwmN-‘izmmiim1t~.-Imzmmsmmmmmmm: mm tam-macaw m." i "vi I.) ' .i i: .i.‘.'.‘ .- in: a - r mm «m 12 WW3WWTHWT'H‘MI mfiwmflwwmrmmmwwmp 5w «mm-n- ENW." mm“! REWI’MW" '1 \i“ 7-,‘_"\‘;1 ’ FINAL EXAM, CHEM 2364 student name 1 2/ 3/ 96 Dr. WEINGARTEN TA name Compound A, C5H304, is optically active but when it reacts with methanol and _ 13. dilute acid it produces compound B, C5H1004, which is no; optically active. Compound A also reacts with water and dilute acid to yield compound C. C4H504, which also is no; optically active. The NMR spectrum of compound 8 is shown below. Draw the structures of compounds A, B and C. NI‘1R of Compound C 2 H's 3 H's Hint: This resonance is for o corboxgiic acid proton ......-.n-...._. 13 FINAL EXAM. CHEM 2364 student name 1 2/ 3/96 Dr. WEINGAR’TEN TA name s... "Tn—m... m. 14. Compound A. C11H1402, on refluxing in dilute aqueous acid yielded compounds B, __ " Cstoz. and C. C4H1oo. Compound B was a crystalline solid, mp 122°, and E compound C was a liquid which gave a positive Jones test and a negative Lucas test. The NMR of compound A is shown below. Deduce the structures of A, B and C. . l5 H's NMR of Compound A complex multiplet i H EWW W1 14 FINAL EXAM. CHEM 2364 student name I 2/ 3/ 9 6 Dr. WEINGART EN TA name :15. During the semester you prepared a sample of Nylon [6.10] from sebacoyl " chloride and 1,6-hexanediamine. 3. Write an equation for the overall reaction. “Wynn”; “A y b. Describe the procedure you followed. omitting references to specific weights or volumes. E a '2‘ E s E E 5 i l l c. List all safety precautions. 15 ...
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