322bf04_e4_key

322bf04_e4_key - Organic Chemistry 322 bL Fall 2004 Exam 4,...

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Unformatted text preview: Organic Chemistry 322 bL Fall 2004 Exam 4, November 22, 2004 E Name Total Initial of Last Name {1 T.A.’s Name (30 pts) (10 pts) (12 pts) (10 pts) (9 p16) (9 pts) (6 pts) (5 Dis) (15 pts) gawk Write the products of the following reactions. Assume normal work-up. Indicate if the product is optically active or not if appropriate. (30 pts.) 0\ R?_ H \c/OY' H— _OH Br2 / H29 X H—L H—(tlé—OH HJFOH CHQOH 047,0” 0 x Fe”, H202 RED" owl H (k —H \Ls&‘N“'pl/\ 0H 3:295:12.) tel-mm 0“ " OH CHQOH M '9' GLOW (K -H H OH HNo3 H 3’” HiOH MLOH CHZOH £13m 0\ RT_H \%/W H2 ' ' -/ H—g—OH H109“ H’fil—OH H20 W “3350 H h. R 0%) ‘4 __—O (1/ / HO H HO—LH Na/Hg , HO H H20 H36 \ 0“ CHZOH p CM“ H HZOH /E\CH x O NH CH 3 H OH N/ 0‘ HO H O (g9 (21,. . ® G) E E E @ carboxypeptndases “N’CM H3 N-SJH- -NH-CH2- -NH- H- -O 3 CH3 hf? NO M? mild b Ph-N=C=S pH 9 2 G F \\ 0NQ—MH’ CW ’C’afl ase L \ not. 3 X (n: “FM” CV5 HOQ /' C M a /\< )4) H r Q ~———- C H 0 ‘CELJ o D Q 0 + h, —>YPHV:HV E 0 U ~gumngH-cmv-af 0“: W W CH2-C—H + H3N +‘/HCN H D I C\41?C‘L~H. / v0 a) [4: CN 3. m 44ch Draw . confornRion for H ll 0\/’ “i 9/ ’ i4. ’3“ Treatment of -D-g|ucose with base leads to a mixture of glucose, mannose and fructose. Write a reasonable mechanism for this equilbration process. (12 pts.) HOH2 H H20H HQOH H HO HO HO H HO CHQOH HO HO OH HO OH k\ < Fructose Glucose \~»\-.MEUD9§E,_ C} ¥ 9 « \\CVIW O ’ HL}\m m J o f . x /L ,6 \ W 0 )MW go. \ l 0 pm ole: m «Ci/vm Q40” H U \N 7 r 9,- Duct) Q H K 4 / ~:—> "KL; O\\ iH ' e - -lyceraldehyde write a sequence of reactions which will yield OH CH20H 02H ‘ Lactic Acid. H«POH , . I (awe I COM 5. What reagent(s) or conditions are used to achieve these transformations? (9 pts.) Ergosterol Vitamin 02 HO Inm Om" I ao@ What is the likely stereochemistry of the 0-0 double bond? This type of molecule is called a (circle the correct answer(s)): triglyceride phosphatide cephalin, prostaglandin,( lecithin l or a steroid. Is it likely to be found in the nucleus, the mitrochrondia, r th golgi bodies? Circle the correct answer(s). (9 pts.) @ fi’ THz-O-HCHgtgHs Z fl. M CH2—o-E(CH2);CH=CH-(CH2 7CH3 6‘" fl filo \/\ CH2-O-lr g<CHsla O O Estrone Testosterone ej [an ck ’unk‘b base—— at“ Jco watery“, \0) (MA Erau‘o. G 002 ' A protein was found to contain 0.29% tryptophane m9 _ What is 3 N the minimun molecular weight of the protein? (5 pts.) 'L ,if'... = Wake: CHHH—O'L'A’L- s 207 [00 v0 ‘ M. ‘ W3 , t M W We. onL¢‘“”qoloq6— V\\ Work out the sequence of amino acid residues in the heptapeptide given the following information. Complete hydrolysis gives Cys, Gly, Hisz, Leuz, Ser. Partial hydrolysis yields three tripeptides which have been sequenced by use of 2,4-dinitrofluorobenzene and carboxypeptidase: Cys Gly Ser, His Leu Cys, and Ser His Leu. If this heptapeptide is treated with carboxypeptidase, which amino acid will be released first? The heptapeptide is treated with 2,4-dinitrofluorobenzene followed by hydroysis. Draw the structure of the 2,4- dinitrofluorobenzene derivative formed. (15 pts.) ...
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322bf04_e4_key - Organic Chemistry 322 bL Fall 2004 Exam 4,...

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