exam_3_s07 - Seat # Name: Recitation Section: Recitation...

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Unformatted text preview: Seat # Name: Recitation Section: Recitation Instructor: ORGANIC CHEMISTRY CHEMISTRY 303 Exam lll Apt-i115,r 200’? The exam |.as 19' multigie choice QLIESIiUHS for credit and 5 till—ins. Please answer the lirst 2G questions on your exam booklet, plus color in the multiple choice answers on the OpScan sheet. ON THE OpScan FORM: {Use aNumber 2 Pencil) {l ) EB your name across the TOP of the form. (2} code only the following information: [blacker] circles] {at Your Name . . . LAST NAME FIRST i blank Space beta-teen Kris! ondfita‘t Home] {bi Your RU ID NUMBER [Start under Box A and continue through to Box I] to} Your RIB-CITATION SECTION NUMBER (Boxes K S: L} {d} Your EXAM FORiyl NMER (Box P) Your EXAM FORM is: 1 See beginning pages of exam for physical constantst periodic table and other information. Rank the following compouuda in terms of decreasing :mciaiitjr (must acidic compound first}. J1 0 o a o F F El m CI é 1>5}4:3}2 B 1}3}4}1}5 C 332:4}531 D 1:335:43] E 3}2}4}5}1 What is the major pmduct at the failowing reaction sequence? 0 Ir N )5 CW 7w 3, What is the major product at the fuliowing reaction? CH2 t. f OH D. "‘“CHE mien reaction occurs? 0 A '“JLDH + fiNHE C} E Am 4. GHQ—‘UH D 1.} CH3! {excess} 3.} heat EH3 HE) '3’ l CH3 CH3 CH3 JEN/CHE E' ECHE 0 DC L Fifi + H20 0 ——-*—-i'* /U\QH + CHE—Cl O D Aok + NH;— O D A [JJ\ '1' CH3—_0_ D '3 D What :sthe product of theft-Mowing mention? a o x CH3 [L F“3 1.: HULCEHEDHmeat [ I +H H "" HN‘» szo- HG ‘x. CH3 ' *2 H36 CH3 NM!“ 0 x H“ OH “,0H3 A- [ 1 a. I H CH3 H C CH Hack /CH3 DH 3 \Nx 3 N a f" H K. a CH / 3 ./ NMm E. CH3 Which reagent undergoes paraclcnrninan‘ttyI naniugaia {1 . 4} addition to 3¥mntene—2—une? O M A. LJA1H4 B. CH3CH2NH2 :3. Alma D. CI—IgC-HQDCHQCHE E. CHgflHgMgEl-r Wioh reaofion produces the ma]or product shown? ‘3' 1.} CHEMgBr A/[K + If“ A. /\)‘LD/‘“~.~ 2-} Hair DH '5’ 1 1 CH LJ' OH I I 3 M B. M 2.} HSCF' {314 o 1.) CHEMgBr DH ‘3‘" o. M 2.} H30+ fi NaCN , Hill ‘3'?“ D % HO 0 1.) CHaLl E. ———" W 2,} W Rank aha the Iollowing soy! substituonto in ordor of DECREASIHG leaving group abitity {BEST LEAVING GROUP FIRST}. 0/ CH3 FH'J o -—r 1‘ CH3 —GH2—D — H519 C "H Br——- CH3 3 D 1 2 3 II- 5 A. 2:533:431 B. 4:335:231 G. 234:5}1b3 D. "Io-4:522:1-Ers E. 4:23-5:1sz How--r can this transfonnation ho aooomplishod? H H ‘? %om o CDEH D A NaDIrUHED o CrOfl-Ififl; c hoat o {CH331C=DFI'SUH E Hlsodmzo Sole-3t the major organic product of the following reaction. {CH BEG Li 1-}THF U + 3 2.}H20. H+ D O HO CH3 Ho CH3 CH3 GH3 CH3 Ha :CHH oHa . H H H :—I H 3 H A a o. o CH3 CH3 fr. It; Whicf- product results from the fc-Hawlng reaction? El [I‘I'Hfl- CH3 GI | || 9 9H2 (EH-a CHa—d—GHE—CH—CHE—CH—CH2_CH:CH2 Hal: H313“ _ CH3 OQHS H33 1:. D. I E QC ...- C H3 Q / C H:a Q 3:" CHE CH3 Haw can this transformation be accomplished? H D .43ch 2}PCC.CH:C12 3:. 1 equiv. {31431.1 Al} E ]} Mgfflhcr 2} C02 3) 2 equiv. CHSLi C 1‘] Mgiathar '2} {CH3}2C=D 3} HEDTJHIU D I} NaH 2)[CH3}EC=U 3} Hgflil-IID E I} 2equ‘w.Li 2} ch=0 BJCHEDHFFSDH *H-Eb 32H EDNa 9' Heat 5' GM DH CH3 BIC-Ha II CI CH3 r" Z Whit h product is formed from the following reeotlon'?‘ 0 || Hat)” oer-oH—m + er2 l H CH3 t“ I a II I Fr. CH.3—CH—CH E. CHa—CH—“CE C. FL-‘.J"‘|,7_a"(3—6.H l l l Br I H CH3 Elr CH3 CH3 {Iii E CHE—CHer + oHor3 / 17’ f An unknown organic oompouno exhibits the following proton NMFI signals: o = p.95 ppm {3H. triplet} 1.25 ppm {El-t, singlet} 1.50 ppm (EH. quartet} 1 E: p E 2.5 ppm [1H, singlet} || II II. The rterbon - 13 NMH spectrum shows the following signals: H o- ng—oI-I —oo CH2 Br o = 9.521 ppm p = 24.5 ppm .5 = 33.? ppm 5 = 43o ppm p: rose ppm Which structure fits the date? 0 CH H l a pH o CH3 HES—CHp-—Cng"-CHp—C-H s. CH3 rng—o—oo . 2, CH3 ll‘a ' ' t? o. oH3-—oH—oH—oooH E j; :CH—CHp-FC—H H f 5’. What is the major product at the tellewing reaction? a NaBHafiN ? CHEGHEN H3 NGHECHB NHCHECHa FL 7’ E. C. H NHCHECHE 3. NHL: H2CH3 E- fé _ Which is a true tetrahedral intermediate that appears in the base premeted hydrelyaie e? an eater? , - + D: l .3- 0 OH OH | | ‘J: +,H || | _ A1 H—iEn—D—R a H—(J:=D-—Fl Cr F-i—J—D\ DI fi—rlz—ue—H E H—tII—EZ- g;- DH DH H CH - CH fr 7 Mia: ie the mater ereduct of the feiiewing reactien? Ci 1. LIAJH x I NH: J__4_,. “H. ' 2.] H30+. H20 “He DH ' r H “v.50 NH; HGT NHe D D E | D \?j D What is the productof me mastic-n shown below? catalytic NaUD, D20 ———-——-——hn- £5.23. ‘7' f . What is the name ef the cumpuund shown below? 0 . CH3 A methyl 3—ethy1hexaneate E methyl 3—ethylhexenuie aeid C 3-efl1ylrl—meflmx}reerhen}rlpentane D 3{meflmxyembenylmethyljhexane E 3 ethyl— 1 —methuxyhexaneie acid ch. J62. Chem. 3GB Spring EDD? Exam 3 1])# Section Harm: Give the prmlunt and a dgtaiicd mechanism using curved arrows to illustrate the rcnttiun shown helnv- . Include all charges an atom: and electron lune pairs [6 {HE}- C! ADI __—p- H30 + {Si-[30H Draw the major prmiucl of the reactiun shown helnw. GH3CH20NE. CHQGHEDH, hfiai D? ‘3; Draw the prnducts A and B {6 pts}. D BFVY I a. NqH A 1JHESD41HEDJED°G B x D 2 NaDH1 H 0 H2003 J 2 DMF & #‘3 Give the product and a detailed mechanism using curved arrows [0 illustrate the reaction shown IJE-Inw. Include all charges an atoms and Electron lam: pairs {6 ptsj. D g _ HECJLCHS + OH, H20, :1. o? 5... Draw N-ethyl-fi-melhylpentanamide {2 pts}. ...
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This note was uploaded on 01/12/2012 for the course CHEM 2347621 taught by Professor Mr.boikes during the Summer '09 term at Rutgers.

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exam_3_s07 - Seat # Name: Recitation Section: Recitation...

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