FinalFall2003Key

FinalFall2003Key - / TAName: Namezélésm Last Name, F...

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Unformatted text preview: / TAName: Namezélésm Last Name, F first Name Chem 2364 Organic Laboratory Final Examination FORM 2 Practice Final Exam Answer Key Dr. Alfonso Dévila Dr. Tamara Nauman Directions: DO NOT OPEN YOUR TEST UNTIL EVERYONE HAS A COPY Print vela' name am your Iaaellinn Assistant's name n every page it YIIII separate my pages FORM 2 1 TA Name: Chem 2364 Final Test Name: KE I Dec-3rd-2003 ’ Last Name, First Name ‘ The exam has 8 printed pages of questions and 1 table. Check now to make sure you have all 20 7 questions and 9 total pages. Put all answers on these sheets. Page 10 is blank for scratch paper. The exam is worth a total of 250 points. Multiple Choice (6 points each, 60 points total). Circle the one correct answer to each problem. 1. What is the correct way of disposing of acetic acid? a) organic liquid waste organic solid waste ' own the drain with plenty of water Cl) trash can 2.What is the correct way of disposing of aniline? @organic liquid waste ) organic solid waste c) down the drain with plenty of water (1) trash can 3. Circle the strongest base. s' c O .. It CH3CH2NH2 CH3CNH2 N113 Q‘Nfiz GHQ—NH: @ B C 1) E 4. Circle the weakest acid. H2804 Q—OH CICHZCOZH CH3C02H 'ozN-Q—OH 5. Circle the least stable carbocation. @312 O9 Q6 Q?- FORM 2 ‘ 2 6. Circle the compound that would yield the following combination of qualitative tests: Positive AgNO3 / EtOH test, and Negative Nal / acetone test. Cl 00 - E / c1 CH3CH2CI \ m Cl A q B c @ 7. Circle the compound that would be most easily nitrated. O 0 of 0? H ENHZ. 03:013. CHZOCH3 A c D E 8. Circle the compound that would yield the following combination of qualitative tests: Negative Jones test, Positive 2,4—DNP test, and Negative Toll en’s test. 911 9 9 9 CH3CHCH3 CH3COCH3 CH3CCH3 013010 (11130011 A B @ D E 9. Circle the compound that would be most reactive with Lucas reagent. OH U CH30H CH3CH20H @4311 @011 CHCH3 A B c D _ ® 10. Circle the compound that would yield the following combination of qualitative tests: Positive Jones test, Negative Bromine test, and Positive Lucas test. CM 0w O, A B C D (19 FORM 2 ' 3 1 1. Draw the structure for the reactant or major ogganic product of each of the following reactions or write N.R for no reaction. Place only one appropriate structure in each of the ten boxes. (6 points each, 60 points total) Show the correct stereochemist when needed! , 51 Cl ‘ “\“I ‘ L, 9+5. NaI 1 6 acetone , é Ll P475. Qt NHCCH; 9 NH: 3 (sis. NHCCH3 1) Nazszo4, H20, H‘ heat + L - _____. NH \ 2) HCl, H20, heat 5 q p-h N02 3) NaOH(aq) NHZ -— - FORM 2 NH2 1) NaNOz, HCl(aq) 0-5 "c ———————-> 2) Z-naphthol Br .0 ll CCH3 NaOH, H20 + —>—CHO —-—————-—> Heat, (dehydration) OH ZnClz ————> 00 1) KMnO4, NaOH(aq), heat 2) HCl(aq) i o 0. H OH + 4 - FORM 2 o 12. Using the alcohol shown below and any needed inogganic reagents synthesize bicyclic ketone: (15 points) OH the following 5 é ClCHzCOCl A) Flammable _D_ dry diazonium salt B) Lachrymator A EtzNH C) Carcinogen I A CH3CH20H v D) Explosive 9 C103 15. Draw a detailed arrow-gushing mechanism for the following reaction Show.eVery~ single arrow, bond» being broken, bond being formed, lone pair of electrons, resonance forms and formal charges. (15 points total) ' ‘ PhCHO + MeCHO. fl» PhCH=CHCHO ‘ heat A) Degrotonation to form enolate‘(4 points) __ H :0 0 H '. u l u A ‘14 n l I + H20 2 H'C‘f‘w H»03-CH 4r") WC:- CH ifoIH ‘ B) Nucleophilic attack (4 points) _. -- . . ‘ 0 . o 0 z ‘l‘ '3 l l! u ._, Ph— 0 H + Hr9-CH *9 “v- C‘l'fircH : 6‘ C) Protonation to form aldol (4 points) , , , . I ‘H *w .. :O'H . O: \A In? H ‘3 'c a an +"5H ._...—————-———- , -———~ Cw ‘. H H H H D) Dehydration (3 points) , . {PM 9, > ‘3‘ .. .. k~c-,E(’/~«CH 1%»thwa +~pH +Hzo: I 6 H ETQH FORM 2 7 16. Assign a structure to each of the following unknown compounds and clearl indicate our assignments of all proton resonances as well: (15 points each, 30 points total) l) KMnO4, NaOH(aq) Wk. heat ‘ 0 2) HCl(aq) cngcntoccnzcuchzco CH2 3 m 3) EtOH(excess), H+ heat Compound A Compound B {5" e k 1 C5H80 D‘s-FE. 1 C9H1604 . H-NMR t : H-NMR t : \ ice" spec ra ‘Fo" Dorm spec ra k“ can A) triplet 52.0 ppm (4H) 6 1‘5 A) triplet a 1.3 ppm (6H) . triplet 6 2.2 ppm (4H) 56‘ “m B) quintet 5 2.1 ppm (2H) mam 0“ in km C) triplet 6 2.3 ppm (4H) 0" en‘m wt, D) quartet 5 4.1 ppm (4H) 17. Arrange the following groups in order of deceasing migratory aptitude in, pinacol rearrangement. (fastest first). (15 points) A) p—methylphenyl B) p-methoxyphenyl C) p-nitrophenyl D) phenyl : E) p—chlorophenyl g>A>£>E>£ 18. a) In the protection of aniline, the acetanilide was formed. How did you keep aniline from . becoming protOnated in this reaction? (5 points) ‘ f " ,Soclkum Make, was added“)? ‘Porm 4L Urge-er \Jx‘Ha 4+2, MEF‘C (Add byproduct. b) In the second step of the preparation of lidocane, how did you keep diethylamine fiom becoming protonated? (5 points) EXCess otte+kyl amine was ' FORM 2 ' 8 19. From the list of compounds below circle a pair that would produce the following molecule: abitozm (10 points) In ’ .. _ [ ‘Cone Jr 0 cone MeOzC COzMe ""COZMe C02Me COZMe 20. Acetic acid can be synthesized by oxidation of ethanol with chromic acid. (:on e COZM 6 C1on e A) Calculate and then circle the limiting reagent in the equation below. (7 points) Show your work E+OH) (Atom 3 c 3CH20H + 2 NaZCr207 + —> 3 CH3C02H + 2 Cr2(SO4)3 + 2 Na2804 + 11 H20 6.36 g 26.2 g 16.0 mL 18M 4.69 g (actual yield) MW 46.08 262.0 98.08 60.06 392.21 142.05 18.02 (g/mol) W x ammo“ amasmx Acou 40.0 W 3W W Sml Ad)” 2 . ‘ OH IZI’Z-o‘a/W‘N‘ncrzo7x2tml MerzOV 0 Bomb N “0.0 4kg..— wa w\ H7504 BMW” .o.\oBMoch0H “x 'OOOVK’ x J": ' , XBMA “7.504 B) Calculate the theoretical yield W of the tie acid in,gr _ (7 points) Show your work 3 a W 0 pa «we 0.108M1 A60“ W: (0m M)“ “1053 Mon accept exikw anSwer C) Calculate the percent yield (with the correct sig. figures) of the acetic acid. (6 points) as: I Show your work . soar} 2 W9 (32‘s x KOO: 723 7a 0&2 727., gsfij’udfiwt Mllep’l’ e rlker omst ...
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