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final key 2005 - Exams can be picked up from Chris...

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Unformatted text preview: Exams can be picked up from Chris Lundby (226 Smith Hall) on December 21 and 22 -or- after January 3. Last First Question 1. Z 2 Name #Name___ (please print clearly) 2 Z0 ID. number 3. ___Zc; Organic Chemistry 2301 Final Exam, December 19, 2005 4. Z 0 Professor Gary R. Gray 5. ___ZQ_ 6. __3_Q Please answer all questions in the space provided. You may not use a calculator, molecular models or any notes. 7. 3 0 8. 5 c? All electronic devices must be turned off! - 9_ ZU The exam must be taken in ink in order to be submitted for re -grading. Total £0 0 1. (10 points) When 3—methyI-2-butanol is treated with concentrated HBr, the major product is 2—bromo-2-methylbutane. Propose a detailed mechanism for the formation of this product. You must show each bond- forming and bond- breaking step separately! [Solver/l ”-21 Pl. (IDH B ?r H3c—c—CH—CH3 H—r> H3C—(IS—CHZCH3 / CH3 CH3 . 7 /H€t {\Bvo H $.41 ® (20 poinTs, 4 each) Give The sTrucTures of The producTs of The following acid—base reacTions. From The pKa values given below, predicT wheTher The equilibrium will favor The reacTanTs or producTs by wriTing "favored" under The reacTanTs or producTs. pKa pKa ammonium ion 9.4 T—buTanol 18 phenol 10 aceTylene 25 meThanol 15.5 ammonia 36 waTer 15.7 eThene 44 eThanol 16 4-3 a. HzO+NH3_—‘*— l—loGD + Nl-hf [MET] ® ® fivoreoll (7; 6:14:23 b. H2C=CH2 + NGNHZ ‘— w‘bmcgl’l “A? “l” NW3 [Ci—5H , 6) 19¢qu {29 c. H—CsC—H+NaOCH3 *1 H‘CEC1el/Uwg + C2430“ .. (D (D Sq SEX flavmggfi @ d. (CH3)3COK+H20 ‘1‘ (engages—i 4— Kai—l [Io-4210] CD a: 'xcwuoveJl Q OH emafi e. CH3CH20NG+©/ 2 CHEC—Hm-DH ‘l” d fl 0"!sz 03 Q) fiauareot @ (20 points, 10 each) Give The s’rruc’rures of The compounds whose molecular formulas and 1H-NMR spec’rr‘a are given below and assign each of The resonances 7‘0 specific hydrogens by placing The indicafed Ieffers by fhe appropriafe hydrogens in your sfrucfure. The spec’rra are referenced To ’re'rrame’rhylsilane (TMS) seT aT 0.00 ppm and rela’rive in‘regral values are indicated. Typical values for proTon chemical shiffs are given on page 10. Cl. C9H1oOz @‘GX erecf 5+FMLJlMV'Qs) a} “6% £53.?) "NWT a singlet 3 H doublet, doublet, J=8 Hz J=8 HZ 2 H 2 H b. C9H16OZ @Qr carved” 5h~itolw€ (Dank agsfinwd‘ E4345 ‘QDY’ a ‘ at 0" doublet, doublet, J=10 HZ J=10 Hz 1 H 1 H 4. (20 points, 5 each) For each of The following pairs of compounds, indica’re wheTher‘ They are enanfiomers, diasfer'eomer's, or' The same compound. H CH3 H36 H and Cl. / CH3 OH H OH b- H OH and CH3 0H 5. (20 points, 4 each) Draw a sfruc’rure for each compound whose proper name is given below, being careful ’ro indica’re The configuration of any double bond or The chiralify at any chiral cen’rer. Cl. L’Io-i 283 Pia/h] 2-bromo—3-efhyl—2-mefhylhexane l r“ wg~lcl« —-~ cit—i Wuwtwg W3 0415943, (Z) 2 bromo-Z penTene g3?“ CHLC/H3 (—zf-Fur E- CSOW’” \ __ / C~——-—-C / \ “*3 1+ (25,423-3-e’rhylhexa- -2 ,4- diene “all @ “CW“ and?» Lnowreut‘“ >c ”=C.\ “RC/H3 dim/Jo la haw 6%: CH3 (44L w 7» Mir» ‘9‘ ea“. moi c a mi (Z)-6-eThy|-2-oc’ren-4—yne “<3 i :c. (.34 WW Ci» iii Aim H/ H (2R,3R)—2,3-hexanediol (answer mus’r be given as a of“; Fischer Pro Jec’rlon) l—lii H 6? Ear wok Cncwrecf O H : , ‘ , i w @ 0‘41“;sz amend CM 1’" 6. (30 points, 5 each) Give the structure of the major organic product in each of the following reactions, being careful to properly indicate stereochemistry. If the product is racemic (i), so indicate. 2% 404,] C. [5470] [7' 22¢] [Wig] H3C H H3C—C—C—CH3 ML hv H3C CH3 H3C 0 —-> Br Br H H3C— c— 6— CH3 W» heat H CH3 Ph H Br Et3N —> H Br heat Ph CH3 Br H NOI ——> Br Fl acetone CHZCH3 CH3 NGOCH3 Br ----*> heat (Substitution Product) (Dc/Hume.) (Substitution Product) :xzc, /Pk 69 l; r WY‘OWfi \H L$0Wr (Elimination Product) W3 /l..l 69 ‘Qr \; mc/ CC“: £6qu“ / \ dwa 7. (30 points, 5 each) Give The s’rruc’rure of The major organic produc’r in each of The following addition reactions, being careful To properly indica’re .s’rereochemis’rry. If The produc’r is racemic (i), so i ndica’re. CH3 1. BD3-THF m I (i) a 2. H202,NaOH “‘OH 69 0 [5”ééj (D = 2H) r 6% cl: ‘5 lf“"£r£aoM—M oncorredf p y» m of: («Lever C50 b HOZC\ lCOZH CH3CO3H a. H ' /C=C\ ——-—>HZO H0 H (3:) C9~é§d H H l‘l' O Irl' @ OOH—l @ (Fischer Projection) c H3C\ ’H Br'z CH3 - /C=C\ —’ H B r“ ‘5 H (Fischer Projection) H CH L, d. g 3 H20 0H3 23-) [f'Z/dz] 6'? Cl CH3 ‘ ' par ' ' " l L 50W r [547%] CH3 6H3 O _ 1. SiaZBH n f. CH3(CH2)3C=C—H 2.H202,NaOH 014?: (Welrc-"Ff @ [422.14,] @ “par wrFe-cf emal 5m: CH3cH—cH— CH3 CH3 8. (30 points, 6 each) Show how you would accomplish the following transformations in good yield. Please write the appropriate reagents over the arrows and, if more than one step is required, itemize (number) the steps in the order that they would be performed. @ /T:/ /' #150961 [Vttf JY a (i ) 2 . H73 r“ @ [wag pgraxLJesé-D Br @ 2:3,,sz New?! CD / [email protected]@ Ch’sél-IMr ”3% H C H3C—CEC—H /C=C\ .3 NM E) H CHZCHZCH3 PM 75/] ”its (0 /. LI. @ CD @ Br l. M3) [email protected] O O 2. 045(06le 0140 6- 3. Addhcy [17/4/ch Li. H Lcroqé9 (4M Chromwwwbksept DXLAQ'MQ Wfifimflfi) 8 9. (20 points, 10 each) Outline a synthesis for the following compounds using the indicated starting materials and any other necessary reagents. 0 from alcohols containing a. W three or fewer carbons 0 ram ll ”EC“ 0+ @ CH3 b. ”$0“ from H—CEC—H H OH , . CH3 GD 49 E t“ 373-7 Om, lit—2,01, fir" g3 H%ECMH_. (D m. KWQWWMJH @ \.MaUl~l-z__, W5 l‘lLQD l.NaNll—z_ 9‘ W3f® / \l—l <——-—- OH'gv-cac—wge—v CH3'CEC’”H l'l LCnleg , N $54211" angst ufi;% 0 \/ CH @ 7) RC03l-l 0H3 /ll 1+ on <__.___ \zzc, H 12H Hun @ H/ \Ofi‘s 0H3 ('1 3' H) CH3) ...
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