answer_key_final_exam_spring_2006

answer_key_final_exam_spring_2006 - Page 1 ofll Chemistry 1...

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Unformatted text preview: Page 1 ofll Chemistry 1 18C Name Ans 00“ K Final Exam Last First Middle June 14, 2006 Dr. Xi Chen TA This exam contains 11 pages and 9 problems. When you are told to start, check to see that all the pages are there. If not, ask for help now. No adjustments will be made later. 1. (9 pts) Name (IUPAC system) or draw the structure of each of the following compounds (3 points each). (a) Benzyl benzoate II CH3CH2CH2CH2—O-C-CH2$HCH=CH2 CH (c) PWMeJl/lo ic Mach—roll; O '6 ~ N “a a “Mi-“twee: (x) O - n n n n n - O 2. (8 pts) The 1H NMR chemical shifts and the carbonyl IR absorption peak of a compound (C11H1402) are given below. Write out its structure. 1 8 4.36m) H NMR Spectrum ( C > Doublet 5 1.2 (6H) (ab) H H (a Singlet 5 3.5 (2H) C 3 __ _ P ._ OH Multiplet 54.3 (1H) (c) H 0’17— C 0 Ola «=3 Multiplet 5 7.1 (5H) (ob H H 8 3 x0“) 0H3 (a ) lR (c=o stretch) 1740 cm" ’— Smicrn) (b) can col) Page 2 of 1] 3. (33 pts) Multiple choice. Circle the correct answer. a) (3 pts) Which of the following is the strongest acid? CH3C|3HCH2COOH CH3CHZCIIHCOOH Cl c1 CH3COOH b) (3 pts) Which of the following is the strongest acid? OH 0 CHO OH c) (3 pts) Which of the following is the C-4 isomer of D-Glucose? H—o=o H-(|3=0 H—(li-OH Ho—o—H H—lC—OH H—lC—OH H—(II-OH HO~(lJ-H HO-C—H H—C—OH l l CHZOH CHZOH d) (3 pts) Which is the least reactive towards water? i? i? S? l? CH3CH2COCH3 CH3CH2CC1 CH3CH2COCCH3 e) (3 pts) Which is the least stable cation? CH2+ CH2+ CH2+ CH2+ OH F NH2 CH3 Page 3 of 11 f) (3 pts) D—Galactose and L—Galactose are Anomers Conformers Epimers g) (6 pts) Which one of the following represents a natural occurring amino acid. It has an K (R or S) configuration. It is a(n) L- (D— or L-) amino acid. I? NH2 51 HZN ~C—COOH H—C—CH2(CH3)2 HzN—C—COOH CHZOH éoon éHZSH h) (3 pts) Which of the following is a D-ketohexose? (|:Hon 1'4 H“C,3=O H—(l:—OH H—CII—‘OH H—(lj—OH HO—C—H H"(|3=O HO‘CE‘H HO_&_H H-(ll-OH H—(li-OH H_(';_OH H—o—OH Ho——(|:—H 0=(';_OH CHZOH CHZOH i) (3 pts) Which of the reagents listed in the following can be used to distinguish between Q Q OH OH Ag(NH3)20H NaHCO3 Dilute HCl j) (3pts) Which one of the following is the strongest base? CH3 No2 No2 No2 No2 : NHZ NHZ NH2 NH2 Page 4 of 11 4. (54 pts) Write the structure of the major organic product(s) of each reaction shown below (each reaction has at least one product). If you think there will be no reaction, write “no reaction”. a) 1. K1+v1no4, KOH, A com 2. H ,H20 OOzH Brz, cat. PBI'3 ‘9 OCHZCOZH —-—* O— ?H COzH 6r o H 0+ 0 c) O + Br\/\/OH 3 Br Wo’lk/VDH A NH2 1. excess CH3] d) AgZO, H20 3. A 0H5 CH3 6’ 32:?“ a o — H10 l! U _, H—(IE—OH M ZHcH + 002 +‘ ZHC 0H H—c—OH CHZOH 1) (EHon 0H >0 H C/Hwo H = O (I: O NaBH4 0” H OH H—Clj—OH ——-—-———-—> 0 H + H H—c—OH o H 0 CHzOH on“) H on H 1-130 /\/\/CO H g) HZN 2 Page 5 ofll h) S? TH2_O_8_(CH2)16CH3 CHWH ll NaOH, H O l .- TH—O_8_(CH2)16CH3 A 2 ‘CHN’H 4' W3 CCH2316 C02 N0?- CHz—O—E-(CHZMCH3 0”” H i) CIIHZOH OH = N NH Cer (I:=O excess C6H5NHNH2 é: = N N H C6 Hf H—q—OH -——-—-——-> | H-cg-OH H—c ~0H CHZOH H ,‘C ,0 H I OH w H j) H2C=CH—CHZ—cle—CH2CH—CH3 A» OH; = w ~0Hz ~oH’ oH=OH”CH20H3 \ CH CH g A 2 3 / 7 avg OH OH k) G Concentrated HNO3 02.“ N0 7' ———————~————-——-————-—> N02, 0' H I) 1. 2CH3MgBr, ether 2. H+, H20 0” 1. NaOH 0 H ) (j 2. C02, 125°C, pressure (a, Caz H m ——_——————-——-———> 3. PF”, H20 excess CH CH OH, H“, A " __ 11) Product of "m" 3 2 g C 0 0H2 OH 3 CHzBr I'NaCN OHZCHzA/Hz. 0) 2. LiA1H4, ether 0’ Page 6 of ll OH "C 0 o ) HO/g go 5(CH3CO)20 o \ ICI _——* - p HO OH Pyridine, 0°C, 24 h “ O / “[3 HO Hf O‘CI/o NaOH, H20, CH3CHzBr q) on —-——————————> o 0H2 0H; CH3 0H3 OCH3 o AlCl r) :2 + {:0 —»3 :C O 0 5. (12 pts) The pKa values for the functional groups in the amino acid lysine are: —C02H, 2.2; main chain —NH3+, 9.0; side chain —NH3+, 10.5. Identify the form of lysine that would predominate in aqueous solution at each ofthe following pH values: pH 1, pH 6, pH 9.5, and pH 12. Possible forms of lysine: +II\IH3 I?in 1?le +TYJH3 +I|\JH3 + (9H2)4 + (9H2); (9H2)4 + (9H2): (912% H3N—C«c00‘ H3N—C—COOH HzN—C<COO_ H3N—C—‘COOH HzN—C—COO‘ #1 ii 1% 1% i1 pH value: 6 '2- i -53.: A. (8 pts) lnsert appropriate pH values in the above space (leave the space blank for a structure that does not predominate at any of the indicated pHs. B. (4 pts) (Circle the correct answer.) The isoelectric pH for lysine (pl) is: 2.2 5.6 6.4 9.0 10.5 Page 7 of 11 6. (36 pts, 12 pts each) Write out detailed, step-by—step mechanisms and the major organic product(s) for each reaction shown below. Be sure to show electron pair arrows for each step. o 1.N NH,1' ‘dNH ll 0 O 2 Ha0+ 2 KW! 3 CHZ’C —- 0H3 a) CH3CH205CH250H3 + Q—Br ' 3 © 3. A Br @r "8r... @gn/Me :ng ——————~> i 0 O " .~ 0 O : u CHgCHzO~g~aCHW OHSCHzO—g"EH‘C CH3, ————5 l e H n m n O 0 fl :0: “ H'OHZ 0H3 CHzo—«lc| ~CH~ SCH; 34—”; cchHzO«g —-GH »C CH; ——j’—*> [5:63 " NH: @ +.- /H 3‘8 ‘3 $sz .. ( 8 oHsono—caw'ca—ls —-*—-5 cHscHLQ—cwcH—— 0H3 a we I M )3 m/C\CH3 .3995 CH: C~OH3 —CH3,0HwH 0’ \ W 3; d; Page 8 ofll u 1. NH ,HCN + b) QCHZ—CH 3 @on—g—I—Nfls 2.11302 A w; 3. NaOH (Neutralization) :4-H Lb) w HO OH .29 Ho on —-—-'> O + 0 “OLGA/05w} A “chimera 0H ' OH H H OH " Q o Ho Ho H g - 1‘? H Ho OOH5 Page 9 of 11 7. (24 pts) Write out the detailed reaction conditions and important intermediates for the synthesis of the following molecules, using the indicated starting materials (more than one step). coo + I a) Br~CH(C02C2H5)2 —> H3N-CH-CH2CHZSCH3 (Methionine) O kSr‘ “ + “ a? I: + er-w(cozCzHr)z —-:> ~OHC002CLHI'); 0 602Csz 0 H) l 'l' W _ c _0Hz wast/H; H..._._30 » #55 2. W390i'lzC/H1‘Bf‘ ’ COzC’sz- COzH + ,4 £13}: + Myé—cfizGHzSC/HS L) z Clot“ cow 4- io’” NwOH ‘ 0cm” + ~Hs»cn~wzwzs<>~3 Pmmi 00):. + w}. + NH5v—CHv-0HchzOSCl-l3 1. .. No. CN ‘l' A @CHzBr‘ ‘h-j‘E OHz‘CE-N 5391—? @‘CH‘z‘ COZH reflux 2 © 2 2 H301‘ O O ll . ) H u ‘ @wL’C”CH_@ lNMEt Eta @0HL__C_? twig: 2- @cHzBr‘ 0025+ Page 10 ofll 8. (14 pts) The structure of a monosaccharide (compound 1) is shown here. HO OH O HO HO OH Compound 1 Please fill in the following blanks: (3 pts) The name ofcompound 1 is: a " D "‘ Gal/Mia Pimage (2 pts) The chair conformation of the anomer of compound 1 is: H0 OH ofiézOH H H 0 (3 pts) Draw the Fisher projection of compound 1: (6 pts) Write out the major products of the following reactions: Compound 1 + aqueous bromine (pH 6.0) Compound 1 + dilute HN03 Pagellofll 9. (10 pts) Draw the detailed structure of a single strand RNA sequence CGUA with provided information. NH2 0 NH2 0 \ N NH N \ N N NH I | </ f </ I N *0 N *0 N NJ N NANHz H H H Cytosine (C) Uracil (U) Adenine (A) Guanine (G) ? I‘” A 1 0H N Cl) (,1 ' “H O== ~ N f O 0 H7. 0‘ O o 0H ‘ NH ' N’Lo ...
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This note was uploaded on 08/18/2008 for the course CHEM 118C taught by Professor Xichen during the Spring '08 term at UC Davis.

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answer_key_final_exam_spring_2006 - Page 1 ofll Chemistry 1...

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