322as09_final_key

322as09_final_key - CHEMISTRY 322aL FINAL EXAM MAY 6, 2009...

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Unformatted text preview: CHEMISTRY 322aL FINAL EXAM MAY 6, 2009 (1) (15) __ (2) (15) ___ (3) (15) ____ (4) (15) “ (5) (25) ____ (6) (30) __ (7) (15) ___ (8) (15) ____. (9) (15) ___ (10)(15) h (11) (25)____ (200) Grader Please \Q‘v Print Last Name First Name USC ID TA's Name M Chemistry 322aL Final Exam details in the products wh , ' 'ng a racemic form of a chiral product. "Workup" me ’ ' ‘ ‘ 33:25 (A) CH3CHZCFHCECH + CH3CH2L1' a + ethane 3 + (one equivalent) (C) (CH3)2CHCH2CH2CH2Br + KOBu-t Cl (D) CH + NaCN CHBSOCH H (DMSO) 1-:1 : + NaI x.» (E) CHr$\Br acetomtrlle CHZCH3 (100% ee) Chemistry 322aL Final Exam Name CH3 h T eat M (A) CsHa' ~Br CH3CH20H CH2CH3 (100% ee) ' d td td l ' B /EE1‘ “0+ major pro DC 065110 8C0 OIIZE 1'2 4 § 0") K (B) CH3 Pt __1 {G 531 11.0 + H2 ethanol “9‘- s D‘JM CH3 @ I L‘d‘hdkfl __ H3 h t (C) + HBr “i? \ "‘4 perox1 es V: 8r + H H3 (1) hot aq Kb 4n04,KOH D l \ M ( ) (ii) workup Hll’CH3 (100% ee) Chemistry 322aL Final Exam Name (4) (15) W CHECHchchzcomt (ii) workup \ __ (B) C6H5CH20H + I +/ .Cr03.Cl CHZCIZ N H FCC C7H60 o O, (C) CH3 H20/ acetone 3 H H CH C7le0 (1) Mg/ ether (D) CH3CH2CH2CH2Br M (ii) CH3gCH3 (iii) workup (1) Mg/ ether /0\ CQHSQH 542315 Luge (ii) marcsz2 (iii) workup (E) C6H5CH2CH2BI‘ Chemistry 322aL -6- Final Exam (5) (25) Answer the questions below. (A) (5) All valence-level electrons are be missing. Place any missing formal resides. If there is no form that structure. ti xCHs * / , = CH CH CHCICH , . CH C\ 3 2 3 “ Cf CH3 (Lg-m‘ H QLLu-a.\ gcku-«l (\'\\rqs (C) (10) Identify the pairs of structures bel diastereomers, or the same compound on ’L can.“ Ay‘ M CHfi\OH CeHS’i‘H .H d! Q‘fiyc 0 M1 VS ow as constitutional isomers, enantiomers, the line below each pair. Chemistry 322aL Final Exam ’7. (6) (30) Circle the correct answer for each question or statement below. M (A) What are the molecular fo structure below? -7. rmula and "U—number" (degree of unsaturation) of the (circle answer below (B) The numbers of valence electrons in each structure below are (circle answer below) I 7,1117 17,1118 18,1118 18,1119 (C) Among the following or condensed phase will be th H3C HCO; 1 11 ganic compoun e strongest with (circle answer below) ds, intermolecular attractive forces in the (circle answer below) CH3COOH ClgCCOOH CHsCECH CHsCHon ALBI AI,BII A n, B A B (E) The alkyl group name of the compound shown below as a Newman projection formula IS (circle answer below) CH t~buty1 chloride isobutyl chloride C1 isopropyl chloride neopentyl chloride CH3 (F) Assign (R) / (S) labels to the stereocenters in the three compounds below. H H H H (circle answer horizontal below) ? a, F I (R) II (R) 111( C CHZCH3 CHZCI 1(5) 11( III (R) 1 II III I (S) 11 (S) 111 (R) Chemistry 322aL Final Exam (6) Contd. '2. add)" Name (100% ee) I A racemic form of the product is produced from a (100% ee) substrate. II A ( 100% ee) substrate will produce a ( 100% ee) product. III The reaction rate increases with increasing polarity of the solvent. IV The rate of the reaction is expressed as rate = k[RX] [Nuz] (Cirde answer) I, II II, III (I, III 5 II, IV ' ypically proceed fastest in which one of the followmg solvents7 (circle answer) CHgCHQOH CH3?CH3 HSCHZCHzCHQCHzCH3 H20 / acetone (I) The more stable isomer in each pair below 18 H3 H CH3 (circle answer below) / /l\/ CH3 CH3 /K/ \ ALBI ALBII H H I II t I II , A II, B I A B (J) Ozonolysis of an hydrocarbon, C7H12 produces the product shown below. The structure consistent with this result is ozonolysis (:7le , CH3§CH2CHZQHCH CH3 (circle answer) Q D D Chemistry 322aL 9- Name Final Exam (6) Contd 2 (K) Which of the following addition reactions of (E)-2-butene is a (are) stereospecific anti-addition(s)? Brz/H2O CHzNz/ether, heat (E)—2-butene ----- - — -> I II III IV (circle answer) I, IV III, IV only IV (L) In the general chemical transformati on below, what are the formal oxidation states at the central carbon in I and H? g QH (circle answer below CH3 CH3 """"" ' ' * CHBCHCHa I +2 , II +1 I II 1+1, IIO IO,II-2 (M) Which of the following reagents can be used to carry out the chemical transformation in (L) above? NaNHZ/liq NH3 -330c NaBH4/H2O H2CrO4/HZO LiAlH4/Et20 I II III IV (circle answer) I, II, IV only II II, III, IV (N) Which of the following carbonyl compounds (X) ma y be used in a synthesis with methyl magnesium bromide to produce t- butyl alcohol? Assum e the Grignard reagent IS in excess and the product is worked up after the addition step. (PH (circle answer below) CH3MgBr + X _ I ' . . _ - _ _ I — I ‘ ' * CngCHg, ‘ I,II CH3 9 1 II LII III chorces CH3§H CH3CCH3 CH3£OEt on y of X I II III (0) Which of the followmg solvents ma (circle answer below) CH3CH20CH2CH3 CH3CH20H 0 H20 onlylV (THF) II, III, IV III, IV I II III IV Chemistry 322aL -10- Final Exam Name (7) (15) Answer the questions below. most stable chair conformation of trans-1,4-dichlorocyclohexane complete the stereostructure for (R)-2-methyl-1-butanol plete names for structures I and II on the lines below the structures. H H thegsLLtlltggwt (LIE 29— .\ “1.7:” D? K%)ZS>H fl What is the relationship between I and II? (constitutional isomers, diastereomers, enantiomers?) d \CkSfi 110 Mt x-S Chemistry 322aL -11- Final Exam (i)[ (MACHzfié B r] L solvent 9H \ ‘VK {Ii-Hal!” C6H5CH2CHCH2CH3 M (ii) Workup .. b ugcumL‘. [ E444 V‘ [ K<H33§;<IL L H Aural. ‘31. K (B) (8) CECH CE CH Ix] N 0" C If; [1; N: J °§j§ti-~¥ H _ .. Swami” [ " {C 2 r] OSREHgb C=CCH2C6H5 EC:- 1;]; [Hbo@ “2;? H» OH 9‘3 CH3, Chemistry 322aL Final Exam (i) (1) What type of reagent is Hg(OAc)27 (ii) (3) What type of plausible key inte + x.» HZO/THF \4‘ $H39H CH3(F-CH-CH2Hg-OAC + HOAC CH3 (acetic acid) III . (electrophile or nucleophile?) akukro ELI \{ Chemistry 322aL -13— Name Final Exam (10) (15) Provide structures for the following compounds inside the boxes based on the information provided. y decolorizes a solution of BIZ/CC14, and reacts with . 1H NMR spectrum of C is shown in the Chemistry 322aL Final Exam , as requested below. Part (A), below, is a longer synthesis worth 15 points. In Part (B)(10 ' Chemistry 322aL Final Exam Br , H W W ()EQi—NNCLN L > W~1 r. (1;) NHL! q Cad. 5“ (9161+ (iii) 0 """"" "* with any needed RMgX reagent 4 0H o "'33" Ho \(Co /CHMBA/ cu -—————~>=‘* U 1-“ ’"> -———~‘z~3 > W” 3 Q ‘4 «Q H'LQOY Lo or or Qwa/ (r? HfibAAZFJHLOITH‘F 0H (“3 Nquy, KoH Appendix 1H NMR spectrum for Problem 10 (B). 1H NMR spectrum for Problem 10 (C) C6"|o HBr HCl HI H2 /Pt H2 /Pd(poiso NaH NaOEt Table of Selected Reagents KOBu-t soc12 PBr3 BI‘Z ned) NaNH2 NaBH4 LiAlH4 NaCN NaOH Hg(OAC)2 KI H202 (peroxides) te) CrO3, HQCrO4 Cl/ amine base ...
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322as09_final_key - CHEMISTRY 322aL FINAL EXAM MAY 6, 2009...

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