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322b_09fall_exem2_key

322b_09fall_exem2_key - Chem 3.2.16 ENXQM 17 Please £2 1...

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Unformatted text preview: Chem 3.2.16 ENXQM 17/ Please £2 1 Print L ast: Name OCTOBER 5, 2009 First Name First four digits of USC ID _ _ _ _ -XXXX-XX TA's Name Grader (1) (15) Lab Day &: Time (2) (15) __ __ (3) (15) __._ _.____ ~ == 8 O (4) (10> __ __ [Mg/‘4” (5) (15) __ —_ <6><10>___ __ Avemjé 7' 7g (7)(14>____ ___. M 27égaéwiéu/{7‘0M (8) (06) _.___ “M We M a M4 first letter of last name I will observe all the rules of Academic Integrity While taking this exam. Chemistry 322bL -2- Name Exam No. 2 ( 1) (15) Complete the reactions below by providing the missing products inside the boxes. Be careful to give all the important organic products, as requested. It is not necessary to give the byproducts or minor products of the reactions. "Workup" means treatment with water and bringing the reaction mixture to neutral pH. 1 (I) HNOB, H2804, heat (A) (ii) workup CH H3 3 (i) 1.0e CH3CH2CH2 Cl/A1C13 (B) q (ii) workup 5 v‘ W (fa/M) OOH C90 M (i) BrZ/Fe @ (C) (ii) workup CH3 8 r‘ CH3 BF3/ ether (D) (C) + (CH3)3COH EXCESS H3 (i) hot, a9. KMnO4, KOH (E) (ii) workup CH 3 Chemistry 322bL -3- Name Exam No. 2 (2) (15) Complete the reactions below by providing the missing products inside the boxes. Be careful to give all the important organic products, as requested. It is not necessary to give the byproducts or minor products of the reactions. "Workup" means treatment with water and bringing the reaction mixture to neutral pH CHZCHZCOOH (i) Zn(Hg), aq HCI, heat (ii) workup (A) O 44‘. muff? CH3 product decolorizes Brz/CCI4 d 4446 (B) H3C CH3 (1) Na, llq NH3, ‘330C (ii) workup O/Kénm Br- 1.0 e NBS/CC] t /\/ q 4 CH ( _ . _ . (“IL M (C) O hv, heat C) 3- + succrmmide )’ (NBS is N-bromosuccinirnide) 6 n I {(246, ~ it (i) SOC12 dc . (D) .. . j 7 f (11) L1AlH(OBu-t)3/ ether CH3 CSHSO CHZBr (.1:- CH3 .L fl Jefiééni 7‘! (E) (i) NaCN/acetonitrile 0 Cl 1‘» C N (ii) CI-I MgBr/ ether “‘1‘" ‘ 3 ©CH3 OCH3 (iii) H3O+, heat C10H1202 Chemistry 322bL -4- Name Exam N o. 2 (3) (15) Answer the following questions. (A) (5) Indicate whether each of the following chemical structures is "aromatic" according to the Hiickel rule by writing "yes" or "no" on the line below each structure. (B) (5) Use the polygon inside a circle method to estimate the relative energies of the II:- M05 in benzene. _—_—--_--_——_—i Inscribe polygon inside circle and estimate energy levels of Place Jt-MOs 1])1 through 1P5 in the above mMQS throuh . , diagram and fill with the 31: electrons of benzene. @flx. What feature in the diagram accounts for the stability of benzene? Clgsg~ s '5 5 SI.- ¢_\u=\\'0 (C) (5) The nitrogen heterocycles pyrrole (A) and jw‘f pyrrolidine (B) have very different base strengths. 5607“” While B has the base strength of a typical alkyl PY/rfi t amine, A is essentially a neutral organic compound. J. M Explain how their electronic structures account for this difference. L a flux 0‘ “at V \ a. ‘ \ k Riv-HAL (A\ \S \ QmM~b g- The mon— bomd‘ “3 L—LJWO“ E.“ Y‘ is Part o-Q- +kg (Lit o‘Q ”VF—cmddlths4v +‘H‘L HULKL} PU U. fir uu-o Ma‘Hcl‘t‘] - Qb‘l-w +3ve’ha-H- E.Mdt"$“P)f‘ u rok-DMqJ-L L ,. ‘Hw N. rs loss o£ W-clcbemilmfiiax t 2 Fr erfi'um 469M “ 3 W 0 ’ ‘1- ‘ “Arm 1m Pvrr‘d c‘c‘c‘mc C -— m pie-\ 3‘J—Dk uu-fi avvm'xx Q—H E. , k MY HEM“ .e Chemistry 322bL -5- Name Exam No. 2 (4) (10) Circle the correct answer for each question or statement below. (A) The order of reactivity (fastest to slowest), ignoring position of substitution, among the aromatics below in nitration is (circle answer below) II>IV>III>I IV>II>III>I © ( II>IV>I>III > IV>II>I>III III (B) Among theI monosubstituted benzenes below, the ortho/para products will dominate with (circle answer below) 3313 1,111,1v 11,111 111,1V (mde answer)@ only I I, II all of them (D) The more stab e arenium ion in each pair below 18 (circle answer below) A I, B I A I, B II 2(AILBI ) AILBII (21113 ICH3 A B (E) An 5N1 reaction will proceed slowest with which p—substituted benzyl bromide? (circle answer below) $1 = CH— Cl- CHO— CF- Y©CH23r __-N.---- Y 3 3 3 Chemistry 322bL -6- Name Exam No. 2 "— (5) (15) Answer the questions below. (A) (10) Provide structural formulas inside the boxes for the names below the boxes. --‘ p-chloroaniline 2 4- -dinjtrophenol /;—bromo-5-methylbenzoic acid (£230 anal» .- (E)—hex-3-en- -one p—chlorobenzaldehyde (B) (5) Provide two reasons why Friedel- Crafts acylation lS often the preferred way to introduce a side chain on a benzene. Be specific and illustrate with examples. (i) PolYoAMchaflo’EaQ-k M \tedls +1: siding pfi§::l‘:fi 2‘05 @ ’N—B—Qi—s @————? ~-»£ «ohm/2v ”:7 (\O, INC—ix ‘21 “\Q 14, %t« fl“ 5M5? 4.911; cfi PA“.‘-+':~\3 3O K’n AQ-I‘Q‘haax , Fwd HL‘E P(¢-.;+sw\ MQM SlOGZL‘K' / O +_ QH3Q~S§SH§%(§\ 13 \HA fit f0 35"?” MO“ 1 ES? mf’ ’1 CH “4 CH «@5224; ,> <qajcsggezgel m x; “70104 b 3-— L L @@ ¢HWDP~1DE SHtF‘T CchLHZC‘H CUMQS : LUsQHéH' A‘ "f ”\bb 6H} Chemistry 322bL -7- Name Exam No. 2 (6) (10) Answer the following questions about electrophilic aromatic substitution. (A) (4) With chemical equations, show how sulfuric acid promotes formation of the electrophile in the nitration reaction. Draw a detailed Lewis structure of the electrophile in the box below and provide its name on the line below the box. Do not write out the entire mechanism for the nitration reaction. H Q 61%)“ .. .. 10‘ .. _~- .".. "—H u-5-§:e + \4 ~O~‘~O—H- :H—b-q—g + .9 679 .v ‘ " .. \ .. Q : . ‘ ‘4 ‘ .. ‘0‘- ..Q. 6) '0 "-55 ' H 63) _, 'v [email protected]_H .- ‘ .' 6‘3 fen (B) (4) Draw all the resonance structures of the arenium ion intermediate in the para- bromination of phenol. H ‘“*""‘""" 1" ““ “Tinnihn . c (Vlad? (C) (2) When a :50 mixture of benzene (C6H6) and hexadeuteriobenzene (C6D6) is ‘Nf‘cf. reacted with Brz/ Fe, the monobrornination product mixture is a 50:50 mixture of C6H5Br 5““ x. and C6D5Br. What is the significance of this result? Chemical equations are not needed in your answer but be concise. wkfiL A.“ ra.*¢ o—G \Dn-cV-JMS 6. C~D \Ao—mci is sung“— +\N.r.k \DWKKU'MS egg—u. Mamil-x—ank T‘af‘i‘e fi-C‘Ft (\Lmoa (5 aml\£ )Kfopfel-sd \MJ“ K ral‘t 0+ ck T1 ace'l—t‘ark (-9 +l‘t3 C‘HQQX (S XmK‘LW km +KI- KDS. Sl‘MCK'l‘kz Sasha-Q QMOLA/m“-— QFF‘ (C. \A‘S‘B" “ma €59.53” \5 +olxpxg<ij +—\~‘( ; baa/AA. \Mklktm Clots “Ac -\-— 91kt) F1“ +kg RES” C0 wSlS‘h «4‘- Q)“ +l~¢ EDI—O Pafld W \b’ik‘tgp 0+ ‘1 JAR-J #J—t-F S419 ~%“Kkfl’m 0‘? RNA/xiv: (0M Mia. «ca-<1” m Sh?” [05$ °¥HLD\. Chemistry 322bL -8- Name Exam No. 2 (7) (14) Provide plausible and efficient syntheses of the compounds below from the indicated starting materials with any needed reagents. H=CHCH2CH3 (A) (7) and ------- - CH3CH2CH2COOH stereochemistry CHZCHZCHZCHg, (B) (7) and CH3CH2CH2CH231- --------- > 0+3 q t C ~ . H M D S Del 1 \ ~ 0 l 3 © 9m «a M ———————5L\‘ ‘ CR1 \ q QACHL --———- (CHM-R4404 CHESHLCHéHZBr E+\\¢\— ECH'L L L‘ EW¢P > 3 a Z. XZLNL' 9’ 9 fii ’r—r ““W‘asvg \ * ‘ @ka—lfHLC—HbgkkL‘ G No \c ’r :2:- (0/ N 02— Nof {ad #4046 ‘F‘fl‘ L H» mm .4 flkCHOG—V-g My Cfuo many (752/44 Chemistry 322bL -9- Name Exam No. 2 (8) (6) Provide structures for the missing products in the scheme below. Note in the final step, sodium acetate and sodium hydrogen sulfate are byproducts under basic workup conditions that provide the free base of the main product. s NHz 30:3 NH&QH3 CH3 CH3 Q conc. H2504 cngNo NH2 N02 HO- H+I H20 heat + CH3C02Na and NaHSO4 as byproducts ...
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