Practestwkey - Your name Your ID Your TA if you completadyourlab work in a quarter other than this pieasa specify Chemistry 108M Final exam m 25

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Unformatted text preview: Your name ......... .... Your ID .................. Your TA..... ....... .... if you completadyourlab work in a quarter other than this, pieasa specify ......................................... .. Chemistry 108M Final exam August 28, 2003 m - 25 oints - 15 oints m- - 20 oints 5 - 20 ‘ - olnts Total (100 p) Probiem 1 (25 points; 5 points each) Complete the following reactions. Indicate by-produots. Do not show mechanisms. I? NH C CH; K 00 + BrCHZCHS ____..2 3 buLanone OH eat H NaOH —_—h- OCH3 O n C + n NH2 —" O O OH “2304 + CH30H heat +,2IC| —'* Problem 2 True or false. Circle the correct option (15 points) a) In the Williamson ether synthesis the use of tertiary aikyl halides is recommended. T IF b) Benzoyl peroxide is used to form the micelles in the emulsion polymerization. T IF I c) p-DibromobenZene gives a singlet in the aromatic region of its 1H-NMR. T I F d) The ferric chloride test is useful to distinguish aldehydes from ketones. T I F e) The base peak is the most intense peak of a mass spectrum. T I F f) Perkin condensation reactions are best carried out in water as a solvent. T I F g) Potassium persuifate is the initiator used for bulk polymerization of methyl methacrylate. T I F b) Nylon 6.6 is obtained by a step-reaction polymerization. T I F i) Phenol—aldehyde resins are thermoplastic polymers. T I F j) Phenol is not deprotonated by sodium bicarbonate. T I F k) The product of the Perkin condensation of benzaldehyde and acetic anhydride is trans- cinnamaldehyde. T IF rn) The length of polymeric chains can be controlled by the concentration of initiator. T I F n) Protic solvents are recommended for the Williamson ether synthesis. T IF 0) In the synthesis of banana oil, the concentration of water does not affect the position of the equilibrium. T IF p) In the synthesis of banana oil, sulfuric acid can be used as a catalyst. T I F Problem 3 (20 points) The IR spectra of benzyl methyl ketone. 2-phenyiethanol, 2-butanol, and 4-methyt—3- penten-2-one are shown in the figures below. Match the spectra with the chemicals and justify your answer by assigning at least two bands in each spectrum (C-H stretching, O—H stretching, etc.) benzyl mettin ketone 2-phenylethanci [I lpectuul [liquld {11:} 2000 1600 - 11""! IF- lpcctru- [liquid “an inquu um s 3000 2000 1500 V (“I’M IR IPGEtm luquid [11:] I200 1200 2—butanol 800 ‘ 800 4-methyl-3-penten—2—one Problem 4 (20 points) a) How would you separate a mixture of the compounds shown below by acid-base extraction? Answer this question with a flow chart. (14 points) 9 0H —C-CH3 OCH-3, OCHs b) How would you distinguish both compounds by 1H-NMFi? Show the signal (only one for each compound) that you would use to tell them apart. GiVe the approximate chemical shift for the signals. (6 points) Problem 5 (20 points) A compound X (C10H11CIO) gave rise to the 1H-NMR shown in the figure. The IR of X shOWed a strong absorption at 1690 cm". Its 13C-NMR shOWS only eight different signals. a) Propose a struoture for X in agreement with the, spectroscopic and chemical information. (6 points) (Jae [JeSsar'é/e 579%“ng (be/cur) b) Justify the chemical shifts (use tables) (8 points), and multiplicities (n+1 rule) observed (4 points). c)Justify the IR peak. (2rpoints) Possié/e 31H“ Ltwain“ fer X : Cl Cl CI i . O .. n \t’ N—— o l O O 7 LF-‘\ Chow-é #ti EL, fr) “JR-36‘ Mart mle file. Srec'l‘l'aiayjzc I‘n/fi=””""'m Your Your ID ....... Your if you completed your Iab work in a quaner other than this, pfease specify ......................................... .A Chemistry 108M Final exam August 28, 2003 - 25 oints - 15 oints _ 20 - ints 5 - 20 oints , Total (100 p) K97 Problem 1 (25 points: 5 points each) Complete the following reactions. Indicate by-products. Do not Show mechanisms. t? NHCCHg NHJL K 00 K + BrCHZCHa 2 3 O + KHC°3+ B“ butanone / OH heat v H 0‘5 a? H L + “10 OCH3 ocJ-t3 O (I: o ‘k 0 H2804 0/ G) H + CH30H (J + H2 0 heat "-/ H OH + 2|CI Problem 2 True or false. Circle the correct option (15 points) a) in the Williamson ether synthesis the use of tertiary alkyl halides is recommended. T I b) Benzoyl peroxide is used to form the micelles in the emulsion polymerization. T ® c) p-Dibromobenzene gives a singlet in the aromatic region of its 1H-va‘lFi.@if F d) The ferric chloride test is useful to distinguish aldehydes from ketones. T @ e) The base peak is the most intense peak of a mass spectrum®i F f) Perkin condensation reactions are best carried out in water as a solvent. T 16) 9) Potassium persulfate is the initiator used for bulk polymerization of methyl methacrylate. T 16 h) Nylon 6.6 is obtained by a step-reaction polymerization.® F i) Phenol—aldehyde resins are thermoplastic polymers. T f® j) Phenol is not deprotonated by sodium bicarbonate. 6 F k) The product of the Perkin condensation of benzaidehyde and acetic anhydride is trans- cinnamaldehyde. T m) The le th of polymeric chains can be controlled by the concentration of initiator.@l F n) Protic solvents are recommended for the Williamson ether synthesis. T@ o) in the synthesis of nana oil, the concentration of water does not affect the position of the equilibrium. T p) in the synthesis of banana oil, sulfuric acid can be used as a catalys® F Problem 3 (20 points) The IR spectra of benzyi methyl ketone, 2-phenylethanol, 2-butanol, and 4—methyl-3- penten-2-one are shown in the figures below. Match the spectra with the chemicals and justify your answer by assigning at least two bands in each spectrum (C-H stretching, O-H stretching, etc.) benzyl methyl ketone 2-phenytethanol 2-butanol 4'methyl'3*penten'2'0ne 1| Ipecuu- (liquid “III D S+16§S IR spec-um (liquid fill! 111w“, £11m QQO~4OS tat) «Ear rat/V0” V (‘14 anti-H. [0th W”? 111 spam luau“ run) OHJ-i Problem 4 (20 points) a) How would you separate a mixture of the compounds shown below by acid-base extraction? Answer this question with a flow chart. (14 points) 9 O’c—CHs OCH3 OH OCH3 M OBI-15 or Cite“; L)‘\\QOH/ \ of mm C CL uecu S i) Held-lat) Lil? 2,) EMF: 0( CHaC‘a. fr) \) A 04,1445 OI amt, afouLm/lj ( \SCur ) b) How would you distinguish both compounds by 1H-NMFi? Show the signal (only one for each compound) that you would use to tell them apart. Give the approximate chemical shift for the signals. (6 points) OH [S—‘ZLS‘Q i? ll Problem 5 (20 points) A compound X (C10H11CIO) gave rise to the 1H-NMR shown in the figure. The IR of X showed a strong absorption at 1690 cm'l. Its 13C-NMR shows only eight different signals. a) Propose a structure for X in agreement with the spectroscopic and chemical information. [6 points) b) Justify the chemical shifts (use tables) (8 points), and multiplicities (n+1 rule) obserVed (4 points). clJustity the IR peak. (2 points) dwsht dwuaflnm: HI x—leb (n+1) a 5+] 51‘ 7 ‘15 @ufiut 1‘ f /)ge 1' ‘l‘ri Id: (hula-+1 Cl -— 1 \/ P Travail. (MI) = 2—H 5T g1.215 +Le _-.~ 2.85 I J1- :q-ZG +0-62—0.0L = 1-8“; 51. = 4.11; +0.13 +0.03 2 3-42. 0 icqocM-' 9: 5t 4n Iii-(Mark; latrines (ex?ec{:aé@ léctOm' ...
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This note was uploaded on 04/15/2008 for the course CHEM 108M taught by Professor Palleros during the Spring '07 term at University of California, Santa Cruz.

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Practestwkey - Your name Your ID Your TA if you completadyourlab work in a quarter other than this pieasa specify Chemistry 108M Final exam m 25

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