key_practice_2nd_test_2004

key_practice_2nd_test_2004 - Name Key SECOND HOUR TEST 1....

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Unformatted text preview: Name Key SECOND HOUR TEST 1. (18, 6 each) In the spaces provided below, give the correct IUPAC names for the compounds having each of the following structures. O\\ H as ($3 ('31’ 00 HZN : OH q\ |SH //o - _ _ - = _ _ _ OCH CH a. CH2 0 gH3eH p_g (5‘ b. 2 c. ,CgQHg 9H g; H / 2 3 OH 9H2 HO OH QHTRH / ‘9 CH3 CH3 ocnzcn3 a. 2-ethoxy-3-hydroxy—6-oxo-7-phenylhept-4-ynal b. S-amino-6-ethylthiocyclohex-5-ene-l,2,4—triol c. 1,1-diethoxy—4-mercapto-2,7-dimethyioct-l—ene—3,6—dione 2. (9) A reaction that opens the cyclic form of glucose, shown in class, to a 5-hydroxy aldehyde can be carried out in the laboratory using an aqueous solution containing a catalytic amount of sodium hydroxide. This reaction is shown below in a simplified form. Write the steps in the mechanism that accounts for formation of the indicated product under the conditions shown. REMEMBER: You may not add any other reagents. Be sure to Show: all intermediate structures that occur in the course of the mechanism, any resonance structures that play a role in the process, what, if anything, is added or lost at each step, and all formal charges on the structures that you draw. e6H N +OH_ =oH ,0 (3H) 3 (cat) CH3~CH-CH2CH2CH2-c” -- H20 \H + + -H ,0: +H H .. 0:695 ,0 'LG CH3—CH—CH2CH2CH2-Cf ' H Second Hour Test (b), Chemistry 302, Fall 2004, Page 1 off) pages 3.(18) The biosynthesis of glucose through the process called gluconeogenesis, stores energy and carbon atoms for biosynthesis of materials needed for cellular life. A key gluconeogenesis step involves forming fructose from a 3- carbon aldehyde and a 3—carbon ketone. The first part of this process involves binding the ketone to an amino acid in an enzyme catalyst called aldolase as follows: (Euro—1303'2 cam-PO;2 aldohse-(CH2)4-NH2 + 02c aldobse—(CH2)4-N=C + H20 I I cnzon CHZOH 3-carbon ketone DHAP This process can be modeled in the laboratory by the following reaction. Write the steps in the mechanism that accounts for formation of the indicated products under the conditions shown. REMEMBER: You may not add any other reagents. Be sure to Show: all intermediate structures that occur in the course of the mechanism, any resonance structures that play a role in the process, what, if anything, is added or lost at each step, and all formal charges on the structures that you draw. + u H‘j [CH3 H+ (9H3 CH3(CH2)4—NH2 + CH3(CH2)4—N:(l: + H20 CH3 CH3 +H+ + -H CH CH H\® / 3 H\ / 3 09:9 :9—C\® CH3 (CH ) CH CH3 CH3 >C=Ng 24 3 \ __ CH3 H +CH3(CH2)4-NH2 Les ha), H\ (EH3 9 i =Q-*(l3—1\\I-(CH2)4CH3 C53 p, CH3 H GD/C_1\\T"(CHz)4CH3 CH3 H _H+ —H20 H CH3 H CH3 \ l .. +H+ \ G) l .. :9_C[_._.1\\T_(CH2)4CH3 :IO *3: “N—(CH2)4CH3 H+KD CH3H H CH3H Second Hour Test (in), Chemistry 302, Fall 2004, Page 2 of6 pages 4. (20) Most of you learned at some point that a cow has four stomachs. One of the processes that goes on early in rumin- ant digestion is the hydrolysis of cellulose into glucose and related structures as shown in the following equation. This process is carried out by an enzyme found in bacteria in the stomach. Humans do not have similar bacteria so cannot metabolize cellulose, and it passes through the digestive track as dietary fiber. O CH20H \‘ r“ HO O CH2051 CH20H CHon crion C 1.0 “2° Home 0 ” OH OH OH HO OH B-glycosidase HO OH mow-"- + H0 H glucos: OH cellulose cellulose H OH H OH CHQOH The process can be modeled in the laboratory by the following reaction. Write the steps in the mechanism that accounts for the formation of the indicated product under the conditions shown. REMEMBER: You may not add any other reagents. Be sure to Show: all intermediate structures that occur in the course of the mechanism, any resonance structures that play a role in the process, what, if anything, is added or lost at each step, and all formal charges on the structures that you draw. CH3 H 0 914914 o 2+ CH3—CH—CHCH2CH2—c” + H0 H ‘H "if Hid; “ ) «in OH (3+1 | | // G) =6H OH - --_ I | C/0 H CH3‘CH‘CHCH2CH2—C\@ CH3 H Second Hour Test (b), Chemistry 302. Fall 2004, Page 3 of6 pages 5. (14) Ethyl isovalerate, for which a structure is shown below, is a readily available chemical used to provide a “fruity” taste in flavorings. Starting with ethyl isovalerate as the only source of carbon atoms for the final product, show how to synthesize 2,7-dimethyl-4-octanol. Counting all hydrolysis steps, etc., aboth seven or eight steps are required. You may use any other needed chemicals or solvents, so long as they do not contribute carbon atom to the final product. A table of rea ents ou have studied in Chem 301 and since the be innin of Chem 302 is rovided at the end of the test. CH3 0 CH3 0H CH3 \ // \ | / /CH-CH2-C\ W- /CH—CH2—CH—CH2-CH2—C\H CH3 0—CH2 CH3 CH3 CH3 ethyl isovalerate I) combine 1)H AIECH2(CH3)2]/ 2)H+ [H20 toluene /— 75 0C H /H O 2) 2 C\Hs //0 /CH3 ,CH-CH2*C\ + ClMgCHz-CHZ-Cl—I l)LiAlH4 / ether CH3 H CH3 2) H+ / H20 PPC / CH2C12 Mg / ether CH \C3H CH CH OH SOCIZ C\H3 / _ 2- 2- /CH—CH2'CH2_C1 CH3 pyr CH3 6. (7) Benzaldehyde is a readily available chemical. Using benzaldehyde as the only source of carbon atoms for the final product, show how to synthesize dibenzyl ether. Counting all hydrolysis steps, etc., about four steps are required. You may use any other needed chemicals or solvents, so long as they do not contribute carbon atom to the final product. A table of rea ents ou have studied in Chem 301 and since the be innin of Chem 302 is rovided at the end of the test. O I l CH2"O‘CH2 Q/CKH several 0/ 0 steps dibenzyl ether l)LiA1H4 elher OR NaBH4 combine 2)H /H20 HQOXalcohol A I 9 CHz-O-H+ CHz—O Nat+ Br-CH2 0 W G 1:) + PBr / ether Second Hour Test (b), Chemistry 302, Fall 2004. Page 4 of6 pages 7. (14) Starting with 1-methylcyclopentene and 2-methyl-l-propanol as the only sources of carbon atoms for the final product, show how to synthesize the indicated product [called 1-methyl-2-(2-methylpropylidene)cyclopentane] that is free of any other double bond isomers. Counting all hydrolysis steps, etc., about seven steps are required. You may use any other needed chemicals or solvents. so long as they do not contribute carbon atom to the final product. A table of rea ents on have studied in Chem 301 and since the be innin of Chem 302 is rovided at the end of the test. CH3 1 C\ / 3 C H C Eggs—a... G? 9H that is free OfMOF W + I CH3 OH CH3 CH3 CH3 /CH CH2 l-methyl-2-(2-methyl- CH3 propylidene)cyclopentane combine CH 3 CH3 N32Cf207 CH3 Il—l 1) 3H3 /THF 0H H2804 / acetone 0 + Ph \Pécxcfi 3 ——.. ” 2)H20P212/31aOH [Jones' reagent] Ph/ (EH3 G . . I butyllitthm CH CH \ 3 _ _ 13/12 \ 3 Ph3P/A Ph\@ #1 ,CH3 ether 9* CH2 0H fl—’ ,CH'CHz“ Ph’P‘C_CH Second Hour Test (b), Chemistry 302. Fall 2004‘ Page 5 of 6 pages ...
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This note was uploaded on 04/02/2008 for the course CHEM 301 taught by Professor Morrow during the Spring '08 term at New Mexico.

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key_practice_2nd_test_2004 - Name Key SECOND HOUR TEST 1....

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