Chem 242 Exam 2 Key - E < . l l i s W l A reaction...

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Unformatted text preview: E < . l l i s W l A reaction showing the conversion of some vegetable'oil to Biodiesel and glycerine is shown below. Answer questions 1 a-f pertaining to this reaction. If is on the next page, i NaOH 0 Vegatable oil + CH30H ————————> CH3\O/[K/\/\_/\/\/\/l + glycerine a. (3 pts) How many biodiesel molecules are produced for each vegetable oil molecule reacted? 3 , > b. (6 pts) Draw the structure of the vegetable oil (assume that all biodiesel molecules produced are the same as I shown above) ‘ n a I o I Q g c. (3 pts) Draw the structure of glycerine. C H 2 D ‘H l CH-D+l l C HLOH d. (4 pts) If you had used propanol (CchHch-on) instead of methanol in this reaction show the structure of the biodiesel molecules that would have been produced. 0 C143 CHLCH1_0—— ‘c' J W i i l l l l l e. (4 pts) which compound is the least viscous? (circle one) a) glycerinc) vegetable oil 1 f. (6 pts) Circle one of the IRS below which best represents the biodiesel from the reaction above—assume that the biodiesel is pure (that is had been separated form all the side products). 2957 3198 ’l‘ I I IT I | | I l I I | F‘_l——|"' I I | I' 35% 3089 2586 2000 » 1596 ar‘y “(In befueen 5a” plates WWENU'BERS Cur ’ x ~. . u~ . x 1* v - . See Jane asae wvswnazks amrmm 1 \ar‘u nun yawn-n c-Ic pin-z: 1 l l l l A t “° I 'n E J ll s l g l a 5 g i i L 9 0m . vfuuiriuv I_T|1 ' bemul’vllffl W E . l mm ster _ <0 2. (10 pts) Sketch the NMR for the compound below: (Be sure to include splitting and integration) CHZOCHa i b 3H 9 8 7 6 5 4 3 2 l 0 3. (12 pts) Circle the molecules below that would only give one signal (one peak) on the NMR 00 0 Ho H Br H >—_:< I CH / \CH3 Q ' O so 3 a H ; _ Br 1 Br i. l l E l 4. (14 pts) Identify the compounds below from the Data and NMR & IR given below. The integration values for the NMR is given below each peak (e.g 45.1, 18.6, , 19.1 and 12.1 are the intergration values.) On the last page of the exam are NMR and IR tables. Is insoluble in Water, 1M NaOH,and l M HCl Is soluble in ether and methylene chloride The 2,4 DNP test did not produced a precipitate. The chromic acid test gave a blue/green solution r m Lflkol The Beilstein test did not produce a green flame. ,M “\DVK The ignition test gave a ‘sooty flame’ ‘ IAVMA‘I‘L r—r-'r l i-f—‘F‘F'l I-r-r—r—rfi 1 r—r-r-I—r! WW (-1'16 r‘l r—r—r’I—Tfis 4 3 2 PPM 1 |__,_I L_.._x L,J Tom“ NMR 451 integral values 18.6 19.1 12.1 854 7. TRANSMITTRNCE 746 700 Gjrnrull-lfir—r—lxi—ic-rzn-i‘rl—in—l i—i-rarur'r‘ mm 3500 seen 25% 2060 150% me capillary {1 lm between salt plates “HVENUHBERS Copwigh, 1993 same 5. (13 pts) Identify the compound from the Data and NMR given below. The integration values for the NMR is given below each peak. On the NMR ignore the small broad peak at 1.6 ppm. Was soluble only in ether .The Bielstein test was negative . The 2.4 DNP test was negative. 651.41 The Chromic acid test was negative. The ignition test was negative uwwwwaufi:,‘Yflwwmmflmwuwvwwu.May...”wafivfinamfiama¢wm,......l.‘......,..,..\... a“- ..-.w..m .w ....l... w.-. _-. ., V“ . .i no. a. . ... 148 3 CH ~o 3 ‘ocu ¢~ LCHB lmll Pdrhd Wivf ppm (fl) ascz sue.e c-wIIl-ru (ll. butu-un ‘Cl? plat-s "fiVE”””BE"° Covvrlnh' nova 6. (13 pts) Identify the compound below from the data, IR and NMR given below. The relative integration values for the NMR is given below each peak. (e.g 15.9,l4.9, 6.0 and 55.0 are the integration values.) . The ‘upper line’ is a magnified View to make the 7.5—4.5 ppm region easier to see. i Prim The Ignition test was pOsitive The Beilstein test was negative. The compound was insoluble in l M HCl andl M NaHC03 The chromic acid test was negative The 2,4 DNP test was negative E Pal/A SfluH‘xn f s i g . E E 88 l; 1‘. 1 r l i. 2 D I g 0 l a a i g g d H .4 ' a n I. a: 0 § 3 a e ‘r—l—r‘ 'l_l" "l l "F'T l'_l——T I T ’T "‘r 4808 3588 am 6 2080 1 a 1068 WWENUHBBRS Cwiahf 1997 800.8 KBP Pel I2? '74. -_,.__...V.____.v.m_n.m. 7. (12 pts) Your unknown is a liquid which you suspect to be an alcohol. You have done thefollowing classification and derivative tests so far: 2,4 DNP test--no colored precipitate present Chromic acid test-—The solution turned from orange to blue/green. Is insoluble in water, 1M NaOH and 1M HCl. Is soluble in Ether You synthesized a 3,5 dinitrobenzoate derivative with a mp of 149—156 C. The Beilstein test was negative who hal 09“ g The IR shows: a strong absorption at 3300 cm '1, no absorptions between 1680 and 1750 cm'l. no absorptions between 3000-3100 cm'1 ’Uo 4,0MA+\C- c From your boiling point you have a list of these possible candidates: Name ‘ 3,5-Dinitrobenzoate Phenylurethane 2-octanol g 174 156 4-methyl cyclohexanol 134 201 X 3-bromo-1—octanol 177 ---- X Benzyl alcohol 165 180 2,3 dimethyl~l-octanol 169 185 7\ 1,3 propanediol 175 ---— (W Benzyl alcohol Given the results above, which compounds on the list could you eliminate from contention. Assume the results listed above are accurate. 2 'bfa'rflo~ l-oc'l'c‘nal "3‘ N0 0—- ’ altolnol a“! Mo )lrfiact’l‘\~(,$ ’ NO I Q. qi‘ 3000,3140 it? Prepauxw we Mamet 1w wad—er Jdluék Extra credit (2 pts) Interpret the following Nasrudin story A certain conqueror said to Nasrudin: "Nasrudin, all the great rulers of the past had honorific titles with the name of God in them: there was, for instance, God-Gifted, and God—Accepted, and so on. How about some such name for me?" "God Forbid," said Nasrudin. l l i l l l i l I l l l i 5 1 . l E 2 E. l t ...
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This note was uploaded on 01/19/2012 for the course CHEM 242 taught by Professor Staff during the Summer '08 term at University of Washington.

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Chem 242 Exam 2 Key - E < . l l i s W l A reaction...

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