Quiz 3 - Quiz 3 Chem 109 1 What would be:11 major pmduct of...

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Unformatted text preview: Quiz 3: Chem 109:: 1. What would be :11: major pmduct of the following reaction? H30 H \ +. M, m r 6. What mutants are required to achieve the following aansl’omrzrion? CHfiHg DMSU 0 ? Una: __.... Hat: H field 014,an A) i.?BI‘3 HaC fl M “ 2 NaCN use: A} ' a) cmcnz LNaGN H30 3N .,_‘ -—————-—-r- a\ E) 211250., C) CHIC“! LBr'ngv ”'0 «“59: C) 2.1mm D) CH30H; LSGCl; HG M 3 H in 1ch cracks ' L Bra, lav £1 ———-—-—+ El Z‘KCN 2. Which of lira following would you expect to mact fastest with the nuclcoyhiie l' (infidel? ’0 CHJCH=C"23' 7A To which side (army; would thc {bllowing equilibrium lic? B) CHsCHzCH2Cl C) (CHahCHCI-lzar D) (CHJhCHCPhCE enacuzs-rcr + HOH :2 cnlcrazsu + KOH E) (CHflJCCHzEP A) m the lcfi 3. Which oflhe fbllowing halaalkancs wcalrl not undergo the reaction below? 8) 10 1h: right C) equally to lire right and lefi Ra: + (311133" -——>— CfiSR + X‘ D) than: is no way lo £51! E) only 8N2, SNI and 32 reactions aw possible A) (CfiahCl-ll 3) (IE-I301 8. ”Which oflhe following is um aom‘rally agood [caving gmup on carbon? C) (CH3JJCBr A) Br D) CHJCHgBr a) OCH; 5 CKJCHzCH'zi C) C] D} 050211 E) I '5. Prerfict the main:— pmduct oflhe {allowing reaction: 9. Several alkyl halides, incluriing iudmnelhaue, are known carcinogens or canccr~suspec1 maren‘als. ‘l‘o destroy thus: materials by conversion to non—cicarrcplrilic species, yer: can react rlrcm with naclccplriiea. Which of the following would be the best for mpirfly destroying methyl larfidc {icdcmclhancfl WEI A) C830?! 3‘ N B) NH3 A) 3 C) H20 /\~‘<Ph D) Na! 3’ N; H E) CH3C02H NH 10‘ Predict rim major product oflhe following mansion: C} ”3 Pl: N; Br c NaNg Pk“ K 7 D) E) no reaction occurs 5. Wlml is the Mpmducl of line following two-step reaction? CF @343 A) 11750, pyridine \ 2) NaCN G B) C) A) CN G G 1” B) E) no Mellon occurs 01': 6 ll. Which oflhc foliowing magenta would best accomplish a typical SHE reaction? C) A) CH30H B) “:0 030 . C) HCN 9) B) KCN E) No reaction occurs. 5) KU‘Bu l2. Which of the following is the bust leaving group? E8. What wouid be, the proper name of the following? i8 A) 894$ 2 B) G C) H0 A)(1R.ER)-ms-l,chyclchexanadiol e B) GHQ-fidrcns-1,2-cyclohcxancéiol F C} (iSER)-trans—Liz—cyclohmcdiof D) " 1)) (i.S‘,2S)—tmna-l,2«cyciohcxuncdioi (33106 E) (Elm-029l,2«cyclol1cxancdioi 5) ‘\ l9, Which ofthc hatoallcanes shown below would react most rapidly with cyanide ion? :3. if the reaction rate of the following mansion is x, (looming the concentration of KCN would give what ate? (2: + KCN —~~——-- ’ c’ . none wcutd react with cyanide ion. A) 2x 13) X0. 8 C o C) x2 :3) x12 A) A E} No change in B) 3 reaction into C) C . D) i) 14. What is the correct smrcochemistty oftlic product of the following reaction: E) E 20. Which ofthc Following can be used to synthesize (R)»2~cyanopeotane from 7 fR)—2«bromnpcniunn? A) NaBr vices: NaCN B) NaCN C) Na! followed by KCN D) NaCN Followed by HI E) This reaction cannot occur A) SIMS 13) 23,38 C) 2R,3S 2 i An . . . unknown compound has been isolated in pore form and found to oxziibit [a is + :56 9) 23.31? , m 4 CH . _ lo (6 . ~ . 1&2). thch nfthe foltowmg might be the structure nfrhe com on“? E} 3R,4R P 31 Hi: . - :5. 5N1 subsfitul'mn at seconéary halides and sulfonaxes is ofien complicated by competing E2 elimination. Which oftite oucleophilcs below would you choose an obtain the highest A) yieid in an 8N2 reaction with menthyl bromide? H30 3 H H36 -“ CH; 5 ) CH3 A) CH30Na H) CH3C02N3 C) ((31%in D) (CH3)3COK E} CgHsSNa - .aiH H3O C) CH3 16. How would you name the ioliow'mg compound? Hag”, H D} 336 H A) (.S'J-ZMiodo—Z-momylcthanoic acid B) (ma-inco-z-mcmyiemmia acid flag (I) (S}-Z-iodopzopanoic acid D) (Ri-Z-iodopmpanoic acid 8) 0“ E) Nonc ofthesc. 17. 'Ilie Walden [aversion (inversion of configuration) is associated with which ofthe following? A) El maction B) free-ratified halogcnmion C) SN] reaction 33) SN: reaction E) none of these 22. Shut-plaza epaxiéatiun oE geraniol gave two products, epoxide E (85%) and epoxide H (5.5%). This mixture of epuxiées represents what gamers! optical purity {0:- percent enmtiomeric excess, Va Ge)? 0 W08 W + mp'rmgom W U 4 Epoxidn1(35%) ,, ($193800?! mac:2 Epoxide ll (15%) A) 0% E] 15% C) 70% D) 35% E) 500% 23. Which othc following molecules represents a mesa compound? E) (3031'! 215. Optically pure (SJ-mommdittm glutamate has a specific mlaliun of+ 24“. What specific Malian would (Rt-mumsodium giulamale of 50% optical purity have? A) + 24° B) . 24° C} — 18" D) - l2“ E} + 13° 25. Which of the following moiccules is not chiraE? o A) B) 0 H Hog: gin m C} Hozc cola H03!) 01-: ”all: AGO?! ‘15“: D) C03“ 0"“ ""CH; 26, How many total sterwisomem oftlu: following an: possible? E) Ml B)2 (3)3 DJ4 EH5 27. The structure of (-}-gcosmin is shown below, Which structum would be. that of‘zis enantiomer, (+)-geoamin? D) GH3 E) None of these. 28. Which of the aménes beiow might be appropriate for the resolution of mcemic Ibuprofen? ibuprofen wax” ’ l: E) 29. What lecllniqufls) can be used to obtain non-mmic compaunds from racemio material? A) Resolution B) Distillation C) Extraction D) Column chwmatogmphy E) Both 8 and C 30. Which of the following is NOT TRUE for a meso compound: A) It is achital B) It will rotate plane polarized light C) it may be cyclic or acyclic D) it is a stereoisomer E) It has a mirror plane 31. How many stereogenic (chiral) centers are fcumi in {thizoxinl ms B}? Q9 It)“ a)” 32. The best (most reliable) test for the presence of chirality Eat a. molecule is A) carbon attached to four differeszt groups B) existanoe ofa mirror image C} non~superimposability or: mirror image i3) two or more isomers :mssibie E) observation of optical rotation in a sample 33, Which of the foilowing statements is not true? A) Enantiomers have identical propeflz'ss except in chisel environments or with plate-polarized light, )3) Reactions invoking only achiml or mccmic materials must produce ach'ual or moaniic products. C) Diasmreomers have identical properties in all environments. 9) Enaittiomers exhibit equal and opposite optical rotations. B) All cfthe above are true. 34. The following moieeule has how many possible stemoisomers‘? A) l B) 4 ‘ C) 8 D) 16 F.) 32 35. The relationshign between the foilowing two compounds is: A) same molecule ‘ E) mention-mm C) diastereomers D) mesos E) confunnn-v 36. A particular macrion produces m: following M0 alcohols in a ratio of95 : 5. The mantiomeric excess (“/0 cc) is: A) :00 B) 95 C) 90 D) as E} none of these (p ...
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