8BFall08FinalKey

8BFall08FinalKey - Chemistry 8 B Fall 2008 Final Wed....

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Unformatted text preview: Chemistry 8 B Fall 2008 Final Wed. December 10‘”, 2007 Instructor: Lievens This exam contains thirteen (l 3) pages and thirteen (13) problems. Please make sure that your copy contains all thirteen (13) pages. If there is a problem, please tell the exam administrator prior to beginning. Please answer all questions. Remember that UCDavis Code of Academic Conduct applies to this exam and all other graded work in this class. Name: V Last First MI Student 1]). # T.A./ Lab Section: ‘ 6 I 12 7 ; {Total(240)l I 1. Vocabulary: Fill in the blank or circle the correct word in bold. (34 pts) A) An allyl cation is stabilized by resonance B) The presence of an amine 011-12) group on a benzene ring during electrophilic aromatic substitution makes the ring electron poor and increases the rate of reaction. C) For 2-propanone th( carbon” / geminal diol form is more stable in the presence of water. D) An OH substituant acts as an ortho/para director in electrophilic aromatic substitution and how many possible resonance structures in the intermediate? '4 How many are “bad” structures? é E) The Q idol COnQnSafiah is a reaction where an aldehyde can be both a nucleophile and an electrophile and react with itself. It does / work with two ketones. F) r3 gig: is general name for a carbohydrate with three carbons. G) ( g (Mpg: ‘ is a polysaccaride that serves a structural molecule for plants, which is made of many alpha etals of glucose. Humans can / igest it. " H) A Sphigégl 5 91d isa lipid made up of one fatty acid, a sphingosine, a phosphate, and an alcohol residue, it is usually found in ngrve, tissue. 1) A E g contains between 2 and 50 amino acids. J) (L - film and «Shell— are two forms of secondary structure in proteins, they are held together by H ' banal: K) Humans contain amino acids with the amine in the :3 position and an L or 5 chiral center. L) A 1 i go paid a is a protein with a lipid attached. M) A _. _ - S anal: fatty acid contains all alkane chain and generally has a relatively low felting point. N) A Ztm now is a neutral molecule that contains individual charges. 0) Plants tend to contain UflSm lyrwl'fd er fats that ar/ solid at room temperature. poly una'l'H P) G lobular roteins are a general type of protein that is spherical and water soluble, while proteins are generally long and thin. Q) A ketone can be a®l¢§leetrophilej it the alpha carbon and a nucleophile /@t the c=o carbon. R) In acid or base a carbonyl can tautomerize to the anal . S) An Wild Cklar‘uh is the most reactive carboxylic acid derivative, while an am {[14 is the least reactive carboxylic acid derivative. T) The A, B, O markers on blood are made up of lipids / peptides carbohydrates attached to the cell surface. 2. (20 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. 1) NH(CH2CH2CH3)2 A) No War/Shun 2) Ni H2 60 OCH3 CH3 CDC“; Brz, FeBr3 Br , B) -’——-——-—~—> : t + x. \ Q) ar@ 0 B 1 0 3 C) Ar r2( eq} *9 .Bgir CHSCOOH GD {9 0 H2804, CH30H20H D) /U\ O O 1) SOCI2 \ E) W/KOH \N 2) NH 3. (20 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction”. km AICI3 5 ’ m C7.) G) 1) KCN G) /\Br 2) LiAlH 3) 1430+4 CH3CH;CH2NH /\CN =2. 4) NaH003 GD 1 OH 77 O OH OH 0H H H> Haécc 3 y yo 0 OH 7 OH 0.25% HCI “0 OCH 0“; o 5 AW 3 Ch M/om} H O (OISLQW'\ BOC’N\(U\OH c 1) O HIN \(O\M)\(°“ 2) H30“ H a HZNW/LKOCH ’1 Eb Cl )\\ fl 3 Bee.de \N J“? c”) '7‘ k6” H3C(H2C)7HC=HC(H20)7C-O—T-H o c J) H3C(HZC)7HC=HC(H20)7(3-O~CH 1) Pd/C’ H2 3 g e O 3 K u’ ‘0 CH3(CH2)160'0-C3-H © ‘57 H 4. (15 pts). Show the detailed reaction mechanism for each of the following reactions. Include the structure of the expected products and all relevant resonance structures. O o NaOH,Heat O 0‘ Q) 09) _q,\5 6) KW“ lyre ck H C2) ax Q46 he) on C " O E 6%) ° ‘ l4 4/ a —- H< g)- f? @B\@U\Fe *\ \JM’; @t‘rg‘“ c n 0 or! G QC” ° 35% ‘ ~ 6 YQ/EQSWEDJQ < Q r e x " c» ONO) +H3-OQ) firm +OHQQ _. l _ E) < 5. (17 pts) Show how you would carry out the following synthesis using the reagents show below. Show the reagents used for each step and the structure of the intermediate products formed in each step. Not all reagents need be used, some may be used multiple times. LiAlH4 NaHCO3 Lindlar‘s Catalyst Jones Reagent HSO” NaOH NaH PCC Ni 6. (16 pts.). A polypeptide (X) gives 6 fragments when treated with chymotrypsin (A—F). The same peptide also gives 6 fragments when treated with trypsin (G-L). After Chymotrypsin A) Met-GIu-Cys—Lys-Asp—Ala—Gly-Tyr B) Ile—VaI-Arg-Pro-Arg-Thr-Asn-Trp C) Ser-Ser—Arg-Giu-Cys—Pro-Lys D) Asp-Arg-GIy—Val-Phe E) Ser—Phe F) Tyr After Trypsin G) GIy-Val-Phe—Tyr-Ser-Ser-Arg H) Asp-AIa-Giy—Tyr—lle—Val-Arg I) Ser-Phe-Met-Glu-Cys-Lys J) Thr-Asn-Trp-Asp-Arg K) Gtu-Cys-Pro-Lys L) Pro-A79 A) What is the peptide X? 7 B) What are the products of the 5til and 9th cycle of Edman degredation on peptide X? A) ‘1. g ‘I Ser-Pn- flit-sir st —Lys- KsP»Ai-e~i1- Tyralie- Vai-Ars— PnAr, 511w ASM’T’P we”? - Gl/y E __ A... 3.. pa F..C (Cinme I Ir H- L-S'é‘“ Wye-tin w, B) ‘ 621. NOS 1 S c Peptide 1) 0 N4 3" NH Pp. X 2) H30“: H20 ON A}: 7. (23 pts.). Identification of Carbohydrates. CHO OH OH OH HO H Hg 0 O 0 OH HO H O OH HO O OH H0 0 CHZOH H H OH H B H CHZOH c CHQOH A _ CHO OH CHO H H O HO O H OH HO H Hgo HOH NH HO H H OH OH OH OH %DCH3 CHZOH HO H O O CH20H D E FCHZOH G CH20H CH2OH O H OH OH CHZOH H OH O O HO H OH HO 7H OH mm CHQOH OH HO H OH OH I 2 K OH J 0 CH0 Hg H OH OH H OH CH0 0 , 0 Ho H HO 0 HO H OH O H Ho OCH3 H OH HO OH H OH OH CHZOH CH20H L OH M N 0 A) Which are non-reducing sugars? Ct ‘3 i 5" HA: ,7 , M Q) '1 VrCka/ Laws» B) Which monosaccarides are L—sugars? E F S K G) C) Which disaccharides are on-linked 6‘ L 6‘) j _ D) Which is a ketopentose? aldotetrose? C) E) Which is sucrose 6' , maltose L- fructose C (3) F) Which monosaccaride contain a furanose ring? C G G) Which is an amino sugar? 9 a deoxysugar? F @ H) Which is B-D-methylglucopyranoside? M C» 8. (21 pts.). Give the proper IUPAC name or draw the structures of each of the following compounds. OHO W 315*th/olroxy Penkm} A) HO 9 3 2 ‘ H OH B) LI’ Bramo- 20,? alimebyl thd‘ Br 9' Jeram- I~Ayalnxy-'2,3¢Iin,gh7l any»; /\(\ C) \/ N \r N - Efiwfl N" [’50P5W,‘ 3 ran‘l‘fihamM D) 72-3,7-dimethyldec-7-en-5-ynoic acid Kr? day" 0 J< E) 0 {4,4,} I Cyc okexane Carbqhoa‘k 0n ) )' ' 1 dtmehfilehy’l cycickx'au car'aumlc. O / , F) 2.6+LvinlN~d;hch\7L Br Br 25- "Ifi‘dibrmanon -2, \ q en- 7-m q 3pb eack 4p”- map . (16 pts) Using the pKa’s given below calculate the p1 for the following amino acids. Sketch glutamic acid at each of the given pH’s. Asn Arg Glu pKaCOOH = 2-02 pKaCOOH = 2-23 pKaCOOH = 219 pKaNH3+ = 8.79 pKaNH3+: 8.97 pKaCOOH = 424 pKaNH3+ =1 pKaNH3+ : 10-7“! pl Arg 3.21 pl Glu ll Glu pH 1.5 Glu pH 3.5 Glu pH 7.4 Val pKacmH = 2-30 pKaNH3+ = Sac. pl Val Glu pH 12.0 10. Show a single molecule of soap labeling it’s hydrophobic and hydrophilic sections. Then show how many of these molecules can be used together to form micelles and dissolve grease in water. Show a chemical reaction that prevents soap from working in hard water. Show a chemical reaction that prevents soap from working in acidic conditions. (10 p8 O WWWKOQ Nag) W W flan Pilaf hydrop‘mh'c l MO .1: 03m by 65!»: (c Q + ('5‘) NZR'CW Molar—a 2 (25 Sold 0 11 a 2 R-C\0€ kl“ +H35‘ R—C~0u -} H o l 1. (20 pts.) Compound Identification. :00 O in: N: [9] VS“ 0 A B c. D E F G H I J / \ /\N/\ f/ \E O \ O \ K o ' ’ N NH , n H '- M N o P Q A) Which of the above are aromatic? A C H N O lPl'f‘cL‘ / V .. Pfr Wrong B) Which of the above are heterocycles? Ar C K L) N o 9 9x5“- M C) Which of the above are Lewis bases? A 7'C‘,_’_G-4 K! L, M L 333,534 0% 12. Show with an arrow the primary site(s) for electrophilic aromatic substitution on each of the following molecules. (8 pts) OH CH3 NH2 0 N N©Z Brfj/ Br f /\ 7 i ON ’l / N02 QRCLH 13. Look at the following lipids: (20 pts) /\/\/\/\/\/\/\/\/COOH OH A OH O u H c K CH3(CH2)1eC\O_é_H O K) Saturated Fatty ACId (I? i B L) Monounsaturated Fatty Acid (cis) CH3(CH2)1BC\ HO O O—CH CH3(CH2)165\ I}. M) Monounsaturated Fatty Acid (trans) D _ O“C~H C3 @ Q ‘ N) Polyunsaturated Fatty Acid — — —P-O-CH OH NH H H E O 6 2 2 3 CH3(CH2)lSC\O_CH Wax O E: H C(H C) H C CH (CH ) g I P) Triglyceride __ __ _ 3 2 4 2 2 26 x _ _ CH3(CH2)“CHZCH‘CH C CH — F O (I: H Q)Glycerophospho|ipid a? | E H H H _ .. CH3(CH2)160\N_CH R) Sphmgohprd “ I H-9 H O OH O HO 8) Aldosterone I} (B O _O-,Ia_Q—QH20H2N(CH3)3 T) Andrasterone 0 e U} Cholesterol 0 H V) Estradiol WWW W) Estrone / / COOH X) Hydrocortisone | J \ Y) Progesterone WAN/COOH Z) Testosterone K O L CH3(CH2)14EOCH2(CH2)28CH3 1% 0 ID each molecule from the list to the right. Use 1 letter per compound. A 1% B v’ C ’c’ D Q E R F t3 G " \l H s 1 L- J N K O L K Which is a progestin? 6' Which is an adrenocorticoid hormone? H Is J or L more likely to be found in a plant? 3— What is the function of C? Male karma-c What is the function of F? E new glow Where is E likely to be found in the body? _ o NE: -7 ;; 4 Which does not occur in nature? A What is the family name for D? ( £19)“.qu 1"} ...
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8BFall08FinalKey - Chemistry 8 B Fall 2008 Final Wed....

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