242 sample exam1 - CHEM 242 SAMPLE EXAM #1 1. (10 pts) Draw...

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Unformatted text preview: CHEM 242 SAMPLE EXAM #1 1. (10 pts) Draw all the organic starting material that would be used to synthesize each of the azo dyes depicted below. (Assume that you are using the same type of diazonium salt / electrophilic aromatic substitution reaction that you did in lab). H3CO N N H3CO HO Starting compounds H3C O N N H3C NO2 O2N Starting compounds For reaction #1 fill in the expected dye product and for reactions #2 and #3 draw all the organic starting material that would be used to synthesize dye product. (Assume that you are using the same type of diazonium salt / electrophilic aromatic substitution reaction that you did in lab). Reaction # 1 NaNO2 N CH3 O2N NH2 O 2N OH CH3 + H 3C Dye Product Starting compounds Reaction #2 Answer Questions 1-3 using compounds A-H below: OH Cl Cl CH3 OH O C [0 [1 [2 68 0 5080 mv np SAm/w 10 /N oms 5110 ex 116 4sc -.6 px at 6 m2ex x 5290 g L/g 0 ro 1 nppy180 x 5318 6 arcdv In 8 2580 582040 lcounttomarkor stmm}b/dA{[3s mersionp wyscr p1d/B{bs n l/translate CA OA}{1e 2.25 rO wD r1380 in1 cp a CopyRig I-9.61980py n 1980 5168 1730r in 25.8 lp cm np 270 l illcm ap S cpt wbo 5 dp mvr 5640ex 145lp ac 2236 5612 2236s10 0 16 p -1.6 onp[{py Inc.25.8setdash}d/cR o -2 2286 lp1.2 0 ec wx x 1730ac{bs24.6 r-4.8 lW 2 -2 /px L/l/lineto prad }bindg ppe2 x 0l ppo lp lt{e}if e bW end 0 r}{pp}{gn/ex dp m dpa}ie}b/BW{wDin/vrO/index o def sg scfdivac gp1 mv w pyf0 -1 setg cX np s f g-1 -2s{dpsc N mvdp1p200l}fpchemdictpy pxtypetype eqs dpcXbW e 0neg 39i2 1 3 scr}b/In{px ZLB g AA}{1 g -1o mdv-1 5p aLpx bW -1 mt 21.62-8sc1980DLBg cw 0 r{DB}{DS}ie s 0 st}{px OA}{1 al24.6rO x-11sc DA}{120-0 np5dvcmec}{al 2286aR 12 m b120180DA}{dLs SP ecWxComputing 0o cYmv cmr 0.4lWOA}{1w1 CA s sn2ZLBx cp 1ixmvdvCA sm rotix0.690 px py xgldvbW-1 5pxac1S]}b/dL{dA 1 SA macp,lill}b/SA{aFrgdvm 0}ifat 12 L/m/mul{dL}if pydp/cYdpcmrtpm p8acbdm1bd L/S{sflt{-10g scScientifDA}{cw 0cp0bs e16xtrfrpf ebL cvradpx s3oix ac gnH xo/cXrO d dp0plt{1opynp e gpstng-17sc1.2DA}{cwedx}{bd}iex ac 12DA}{2.25pacstCB27ppcpwy pg pxL/mv 1a/px1xl02/lp 9.61.5cm5 -820r-9.62smbdLaserpysDA}{dLCambridg/dxarraydyL/ixdvlin0bslnegatOA}{1.5 bspyor{4 clippath/L{loadlaL-1rne{pyels st}b/OrA{pyormlcp16.8np1987, pysav0dvmp-1emv1180acgLBag ly0nsccmpp}{2lput4illrOsx gcp/movlpro}ie}b/AA{nppdy -11pp}{sqnegstpp 1986,gpx-9.6 n/eyIaAr3080lsm57622]B [9/bd 0}ifacpx 1 smlrOSAstlWbd /bddpn19.6smsc/cXaRwb dp RA}{6180b2071latlrwyePrep DSt0apd}b/bspybsarc90 reqcv16ppsm5860sgcm0smdupend8SADT}]oillxgedefe0n3pSAp SAChemDrawOA}{1SAst}{0py sro0a}ie}b/WW{gst}{Ascsiic0.5 0wx}if np lW0mst}]ewray neg4 advecetoAc}{0.5}b/d/de l 0fDA}{cw248negf0so5640s/g f1DLBxcp3e1600sc3py s2revdpwyrlinetopxill1L/mt/matrixdv 0rlt{ppm/aLgpp3602.25rayraO ppill2198012pympp13.375r0gne{bWdp1pxxcmpne{bWgpyOBdv 24esmv0g/wbr}b/OB{/bSsm}b/CB{np[{[{CS}{CS}{cB}{ 0 lpys2-153xnppl htst}b/HA{lWrpute1.5-1-1L/ie/if5080402.2dv{neglpwm0.51wpysetg{OrA{galmssmst}{1.0sdvpx0rpp}ifL/n/n xwppl1680WIrestore801scaLpOB/bLrot2.2apsqsmneg360-1eIpy1o5{dpcmglpro4.8eqmv2scacppixexcmll}{x3d/wFarcrOrms L/tr/transfrOLB mvarcnclip}b/Ct{bs-.6SArdv0sclpelseDSt}ifOA}{1larcprOWIDSt2Dbill0pxelpyr4wxAA}{1-2g0px2120 16.8wp L/gpApxmv8lwF2.25smpxsg0ley0rO5ac7pg0cmmv-1rtrwgCApxalmvxx-1pylslnesmAA}{1g-1sm2xCA1DA}{180lr4steqmv00cYr03 userdict/chemdictmv1put/N120180tr/dys-1n/dx12wFep5lmspx0spsgCBpf3mt0fgsne{bWa/pycmpxxx0r}ifap21.6ngwscr-1dvdv %cwgilldpscgmv-1sl2rorill}ifdict8Nxp{DD}{DS}ienegrot0dpn/dypbegsc2721.61.5pSA0DA}{270st}{Ascepg4xac-1-11py Ac}{1.e 0g 2 r/g 3 a}b/PT{8 L/x 20 at end}b/Db{bs{dp 0.6d HA}{dL 2286 5820 -1 rad 8 beg a}{ex negOB 5640]B ill 1380 5080]B l 3080 5290]B [6 2580 5110]B mv 1680 5290 s 0.3 5 61 5860]B cv eq chemdict 8 /py rad beg 2 SA -1 1 sl st}{0 0 r}{g 2 beg 0 lx g l/b{bind 40 g 180 st round -1 1 3 sx e g sc}b/Ovdef ne cp 2 /bb 0g i def lWS}if r}ie}b/Cr{0B p m g o ex m dx s{nH a p x 1l c s 0 d/a A B O OH O OH C H CH3 O D H N O O O O H HO E F G H 1. (4 pts) Which compound(s) would give both of the following results: 1) decolorizes bromine solution and 2) is soluble in 1 M NaOH. 2. (6 pts) Which compound(s) would turn chromic acid solution from red to green? 3 a) Which compound(s) (A-H) would react with 2,4-Dinitrophenylhydrazine. Draw the structure of the 2,4 DNP derivative for each that would react. NH NH2 O2N NO 2 2,4-DNP 4. You suspect you have a ketone. You have done an 2,4 DNP test, a chromic acid test and the solubility tests to come to this conclusion. These are the only test you have done so far. But you are beaming with confidence so you continue on and make a semicarbazone derivative. You isolate a white solid with a mp of 155-164 C. Below are listed your possible unknowns and derivative melting points. State two courses of action that you would take at this point and explain why you would take them. Possible Unknowns and derivatives: Unknowns 3-heptanone 2-heptanone cyclohexanone 2-bromocyclopentanone Semicarbazone 167-168 166-167 133 176-177 2,4 DNP 205 206-207 155-156 204-206 5. A student attempts to make an acid derivative (by basic hydrolysis) of the ester shown below: O HO O OH Br 6M NaOH reflux aq HCl Precipitate + Water soluble product OH After refluxing the ester in 6 M NaOH for an hour the aqueous layer is extracted with ether and then acidified to pH 2. A precipitate forms and is collected by filtration. A water soluble product remains in the water layer. What is the structure of the isolated precipitate? What is the structure of the water soluble product? You attempt to make the 3,5 dinitrobenzoate derivative of an alcohol. The reaction is shown below. Draw the mechanism and product of this reaction. What would be the consequence of water getting into this reaction? Draw the expected side product. Write down all the derivatives from PLKE #54 that involved the same mechanism as the one shown below. O O2N Cl + HO NO2 ...
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