Summer 2003 Test 3 - Chem 227 851 2003 Test 3 Dr Welis Home...

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Unformatted text preview: Chem 227 851 2003 Test 3 Dr. Welis Home IR “'1 Score-#ops'oanx3+ossay= xi+ [0 = [(30 “fir/1]. ESSAY: Write. the mechanism for tho roaction below. lfl points W O I I'm *1 t H” ’1’ Label any transition state by . VJ ER- f 2H;th m I‘- Show clearly the stomoohomistry of any transition state or any intonnodiato, and especially the KN“: fifth! _ product. Explain tho origin of tho storooohomistry oftho product. Mg. mme l'. fl a 3T— EEhC—Célm Et—g'r— “I (L/ / \ EtDH / '— ~\ ” Er 5+ me. E: r t ,C #- (fist o' “a an H Pw-wiwr /0 +fo“:1Hh“ {Dip-1m 1* 1a.».é; 'at'fo‘fii'r 1. Which compnund helnw i5 vinyl chlflritie '2' c1 c1 c1 (:1 C1 Cl c1—\\ > < : _ i X WEI RI ® B c n F- 2. The hesl name far the cnmpuund 2 is. A. l-cthyl-EQ-dimefliylelhfim cfs—3,4—dimeth)rl~3~hcxcnc C. c'iS-Zj—diefl'lylbutcnc % D. 2-methyl-2—pemene E. [E}v3,4rdimathyl-3-hcxcn€ 2 3. The best name for Ihe compound 3 is A. 4ethyl-3methyl-E-heane ® 3411113Fifi—dimemyLSvhcptcne C . L'ES- I .ldicihyl-E-sen'-pcnt}rlethene @ D. l,E—diethyl—I—melhylr2rpmpylethcnc E. [Z]-3ethyl-5.fi-dimethy]-3~hemene 4. The best name for the compflund 4 is (D 4-chlflmcycluheptyna Cl 5' B. 4-chlnmctync E. C. cir—4—chh1m-I—Dctcne H D. {ZJ-4-chlurn-l-flctyne 3 r? E. [Z‘J-chlnrnA-heplyne 5. Catalysts increase the rate of reactions ® decreasing the free energy of activation tool) B. lowering the free energy of the reactants [18°me \% C. lowering the free energy of the products (Samarium) 1'). decreasing the free energy difference between the products and reactants {r160} E. inverting every other stereocenter 6. Formation of alkenes by hydrogenation with platinum is difficult because a. the two pi bonds of the alkyne can not bond to the metal surface B. eation Formation is limited to unstable I” carbocations C. skeletal rearrangement is more likely D. alkync hydrogens are more acidic ® alkanes are formed 7. Cycloheitene has been observed in the trans conformation at low temperature, but rapidly converts to the cis isonter upon warming to room temperature because A. it is a trisubstituted alkene (3 ring strain is large (I. the dipole moment decreases D. sp2 carbons are never stable at room temperature E. oyeloalkenes can exist only at low temperature 3. The basis of the Hermann rule is It. formation of the more stable alkene Ft. formation of the least strained ting Q [7. formation of the most stable carbonation D. planar molecules of ions will be attacked with equal frequency from either side @ steric bullt directs reactants 9. The basis ofthe Markovnikov rule is _ A. formation of the more stable alkene B. formation of the least strained ring (9 formation of the most stable carbocation D. planar molecules of ions will be attacked with equal frequency from either side E. steric balk directs reactants 10. The basis of the Zaitsev rule is ® formation of the more stable alkene B. fonnation of the least strained ring Xq' [3. formation of the most stable carbonation l]. planar molecules of ions will be attacked with equal frequency from either side E. steric bulk directs reactants l 1. Hydride migrations will occur Gt.) to create a more stable carbocation __, L.@ E. in strained alkynes V." “L! '5" ' 5| Li’i; a . r a :1, s a i” L L. onlyr In newman projections “ ..--' D. in gem—dibalides ll .flr L .1; fl 5 a. in vic-dibalides 15 {21’ 5 foot. ' fth ..r Cl’le 1% at“; 12. Compound 12 is most likely . /\ ® pentanc E. E-chloropentane Propync C. 3—chloro—2—pentene 2} CH3Cll2Cl R D. E-chloro-E-pentene 3} H Em E. Zehlorohutane 2 13. The best we}.f to make the all-tcne below is MW on lot Br “lefib'i HP: 0‘?- i’ifsl mile '3 W —.II- Plugflnnfb (“It '- bin-j; d...- KMnD4 . [CHflsfl' + also a. E lequw-HBI ' n. no too a. Cold.di1 {Grimm-1 3 2 casoa 14. The rate oran El and an 3N1 reaction is related to (E Iorrnation of the most stable carbonation u” E. formation of the most stable alkene in the transition state it Q C. steric bulk directs base to a less crowded I?) proton it. D. not quite clear. but the peroxides are suspected participate in a free radical mechanism 1( E. the amount of time allotted to laboratory "t" 15. There is restricted rotation about a carbon-carbon double bond because A. ring strain would go through the rooll ll ll E. steric bulk will not allow the trans conformation C. steric bulk will not allow the cis conformation D. sp hybridized orbitals are linear (9 the p orbitals cannot be parallel during bond rotation ma G- aflh‘w bromine in CCL: produces . Br F 014 I Br DH “.0 Cu.” “.\rC 13/.” D Hfi‘y \W H G Hg,»- 1 \flr‘ch 21: H a CH CHEC H3 H H M a X X E“ ‘5’" 16. The roamion of Irans-E-pcntene with M oWoflH} H ‘76 GWQWC Hnga H J? CHE. r 5W" in”; C. C) 3:23 H CH3 H Hw l \ H 3 17. Which oflho flollowing would yield a mom compound ? '1 | 1 HWC L»! 4 L: :14: X 6 no o “if U Br 5 4 "LI ,4 Emlbumne _2.... cfs—E-butono —" M f m H10 zjwarlsoacgficfit} 1 'l B C D. allofthooo 0H “14 rmns-E-butone gig-3MP E. mm fifthfiafi H w Lo, \53 1:ng _‘ 5am ‘I I flu? $1 TA flab PH c. |. 18. How many isomers ofare possible o-chiorovE-he tone #4 #5 P .K D A. one B. two 2. threo @four E. eight /\-:-____—"__ - H 19. How many isomers of are possible fichloro-E-mefllyl-E-heptane A. one @mn t. ihroe D. four E. eight m L" yin-ow S’i‘tfmunw >7‘J a J1. 20'. Marknvnikav additiun afHCl l0 pmpene involves A. initiai attack by chloride anion is B. initial attack of chlorine atom 1k b2? 1&4. F LII C. funnatiun 0f pmpyi Cfllifll’l D. farmafian of isapmpyl cation v" E. iaumerizafion of l-chlompmpenc Consider the following rennin-Ila for questions 21 and 22 1 equiv. PIE; 1 equivHBL -— —C—H CH3 D: 21 paraxidea 22 FT P43" L145-c.-;~.g-r14 Cldih-irl—C—“fl 2.1. Campound 2] is . Al, 51'. ID: ‘1' C113 H CH3 H CH3 Br . H ‘c=c’( “Hf: “Hf mic—Cf I] _ r/ H H Br H/ H H}, H B (A B. a. n. 22. Campaund 22 is CIIL, 1? Ella; Il-I C1113 all Eli]; 11-; Il— — ~—Et H—‘— —H H—C— 1—H Br— — ‘—~H r Er Ea IT! 1l3r H: gr Ii K/ A. a. G) n. The majer pruduel m‘" the reaction below is _. A CH1 H CH3 H ' l' I CH3 1-} H— ‘_ ‘_H I HE" H— —- —-H \C: K 1... ‘r ‘r g f v" H Br Br [-1 H ' . H E3 ' H C Gilt 5* D CPI” fil H—-(E—-([“—-Il H-—lf-—'$'—Il fibr Br Br H H 24. The major predueleflhe reaction hBlDWiS _. CII‘IE If] R. [3'13 If CH H :— .— i=3 L H_‘]" Y H H——fi3—-F-—Il Hf: .(\_H peroxides H Br Br H I ' c. CH H 11- Ci H 1% P“ W |3 I 1I3 r (1—0 H H 25. The mfljflr Product eflhe reactien belew is _. .1. CH3 Iii 3- CH} JH CH 1}— ‘-— .-—H ‘ _ Q H | } 0504 F E (f 6:: HI: <H :2; NaHSU; 303” U D :. ©CH3 H D' CHH H UH 0H H H The majur product of the I'eaetien below is_. A- GE} If R CHL H CH . , H__ _ L_H x I__- x '3" ,“ thU.. 'f ‘r f g {:E‘ ‘ I be H Much {J 0 2’ K Enlidll H H C > ' (:11; H 11- CH3 {1) f | | + I {1“ H_" Q0 Elf + 20 ID "a UH 0H 27. The major product nflhe reaction belnw is _. A. CH3 (EH3 3+ I $ CH1. / H03 H—(f— —H _ CH —'CEC—CH ——h- 3’ CK 3 3 Elma 0—D O/C HO f ‘3‘ CH3 gig R ' . ,cx H—‘(E—(E—H CH3 UH UH DH Consider the isomerizatinn (3F W to 23 below for questions 28 and 29. {Er H. mw‘riud NIH“; CH1 CH3 ' ' H I x ‘__".-*" 1 /C—C\~ ——I- Br i—CH; {31-13CH1 1" Emmi; W X CH3- CH1 )Cz CH3, H 28. jis . , ® HEr m 9.: k.qu Km! " B. H'Bn’pemxides ‘J‘ C. Brlfllgfl D. ELU'fEtDH E. Etfl'fEtDprcmxides 29. kis A. 1-11}: B. HErfiperoxides C. Emil—120 D @EID'IE'LUH E. EIO fEtDpremxides ...
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Summer 2003 Test 3 - Chem 227 851 2003 Test 3 Dr Welis Home...

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