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225Sp09 Test 2 Key - CHEMISTRY 225 TEST#2 1(12 g 2(17 NAME...

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Unformatted text preview: CHEMISTRY 225 TEST #2 MAY 29, 2009 1. (12) g! 2. (17) NAME - V“; wt-V 1C4: 3. (23) G O O D L U C K I 4. —H_ (13) Atomic numbers: 1-1 =1, C = 6, N = 7, 0 = 8, S =16, C1 = 1?, Br = 35 5. (10) TOTAL (75) l. (12 Points) STRUCTURALISOMERISM. a. ( l“ 6) Consider the cyclic hydrocarbon (compound A) below. ll\\/‘ “*2 (Ah Call-9 E ‘ CHQC H3 [ ©< : CHQC H3 i compound A I cyclic structural isomer acyclic structural isomer (MAJ 011,44- 0 (2) Provide the IUPAC name for compound A. 4 if ._ Cl \ eruHA l c a-lp a e u» L i cut o (4) Write structures for a cyclic and acyclic isomer of compound A. b. ( (6) I (5) Write structural formulas for all mofiobromo- derivatives of compound A i mac/153v / altar/2, CAL cu lK>< . < lK)< 3' ‘ (/hfz CAI; Ulla up; 9H153r isomers o (1) Circle the structure above that would be classified as a virgzlic halide. 2 2. (17 Points) ROTATIONAL ISOMERISM AND STRUCTURAL FORMULAS. for compound B. o (1) Directly on the original Newman projection identify two groups that are gauche to each other. I (4) Write Newman projections for two additional staggered conformations of this compound. a (3) Circle the least stable conformation and briefly defend your choice. TL“: C.1~rfL{i mw‘lflrwalwfl. ‘1‘- ll»: Weasel é'l‘ttLla! Le- ('Cthg .l‘ \Aac, "LW’D if .j an» (LL; "H_¢‘l—.{:ba r: 110-“;— {\ 7ch. “EL-fl? a; L a \H.‘ evil? take-f. c277:- €C.P_ Edd” auflLz, mmF-walgfi drfrlf-r fillies-Ll- ( heal/”Tole {Fjé‘lvcugsu b. ( f 9) I (2) Write a condensed structural formula for compound B. o (3) Complete the “wedge and dot” representation for compound B. o (2) Directly on the wedge and dot structure: -highlight the bond about which rotation is being depicted in the Newman projection. -circle all tertiary carbon atoms of compound B. l Gig 0% CAL (ix-4 QUE Mfg i we condensed structure! formula compound B I (2) How many signals (lines) would you 7 expect in the 13’C NMR spectrum of compound B? 3 3. (23 Points) CURRENT EVENTS: UNSATURATED COB/[POUNDS IN THE NEWS. a. ( 1’ 3) Chemists at Boehringer lngelheim Pharmaceuticals, Inc. in Ridgefield, CT have developed a new method for the synthesis ofvinyl sulfones [Tetrahedron Le”. 2009, 50, 2870]. Among the compounds prepared was the molecule below as a pair of geometric isomers. The major product had the (IQ-configuration. Write a jagged line formula for the compound that shows the geometry at the double bond clearly. I—i CH30H20HQCH2$=CHCHQCH20H3 W SO A . Ar = aromatic “'09 jagged tine formula b. ( / 3) An article in the May 11 issue of Chemical & " Engineering News identified several exotic molecules with “extreme” “an: /~" ‘ carbon-carbon bonds. One of the compounds wasa- highly / xi t substituted derivative of ttiafillyalene, compound C to the right. On triafulvalene, compound c ‘ the basrs of structure and bonding account for the fact that compound W C is a remarkably unstable alkene. Be specific. Earl,— TL: ntx Cfi‘L‘buL fl \{V'ridP-\V€ti‘twfi ”16' LiLv'mlt-zeri {L +6 ““on T aiflw ca 0.1Ll'hig. Ove- afar-:11; 4.9 “M ‘- Lomrifi.r1¢f vague} L— m-«(i (13 L LP», i: Lelia l9 (”Z/Om; l-l-Lrvc Lcwcvcr can/Z: "flit magi—voiiwvd ‘l‘o OL’Dw'i (00" A; :2 L‘c‘g’ a“ ewe/"A’s“; GWC‘U“J “3/21 0” L? 9" *6‘}-‘-"-\ c. ( / 9) Chemists at San Francisco State University synthesized the highly unsaturated compound 6-methyl-6—vinylfi11vene below was recently [Tetrahedron Lett. 2009, 5 0, 23 81]. rotational isomer fimethyl-G-Vinylfulvene CC? Hit) a (l) Determine the molecular formula of 6-methyl-6-Vinylfiilvene. I (3) Directly on the structural formula of 6-methyl-6-vinylfiilvene: -circle the vinyl group. «write in all allylic hydrogens and label them as Ha. a (2) Write a structure for a rotational isomer of 6~methyl—6-Vinylfillvene_ o (3) Complete the reaction of 6-methyl-6-vinyifiilvene. You may assume excess hydrogen 4 d. ( l 4) BONUS QUESTIONI Famesol, a naturally occurring sesquiterpene obtained from lily of the valley, is an allylic alcohol. The IUPAC name for famesol is (2E,6E)-3,7,11- trimethyldodeca-2,6,10-trien-1-ol. Using any appropriate notation, write a structural formula for famesol. HINT: the molecular formula of famesol is C 151-1250. i. i “\ \A/K A014 (25,633.111-trimethyldodeca-2fi,10-irien-1~01 e. ( / 8) Cis-pellitorin (structure below) was selected as Molecule of the Week for the week of April 20, 2009 on the American Chemical Society website. Cis—pellitorin is a “pungent flavoring agent” isolated from the tarragon plant. ! __ . —-- ~ s I I O Mam WJ‘Lr/Y / f II-IJ: I 1+ cls—pellitorin geometric isomer o (1) Identify the circled alkyl group by its IUPAC name 2 " M t— i ~49 ( i; JL f 7 o (5) Directly on the structure of cis—pellitorin: -Iabel each carbon-carbon double bond as E— or 2-. ~use curved arrows to locate all bonds about which there is free rotation. The first one has been added for you a (2) Write a structure for a geometric isomer of cis—pellitofin. 4. (13,Points) STRUCTURAL FORMULAS. Write structural formulas satisfying each of the following descriptions. I (2) A Newman projection for butane in 0 (2) Tetramethylethylene its fiJlly eclipsed conformation. - (common name). at My, (A; We \m,< we 0‘? I (2) A compound, Cqu, with five structurally unique carbons o (2) 2,3-dimethylcyclohexene M a (3) Two compounds that would be converted to 2-methylbutane by catalytic hydrogenation. I (2) An allylic halide szmxlC/{é @v 5. (10 Points) MULTIPLE CHOICE, Write the letter of the correct response in the space provided. lg How many signals would be expected in 13‘C NMR spectrum of the compound to the right? A. Three 13. Four C. Six D. Eight 1; Which condensed structural formula represents a pair of geometric isomers? A. cI-s,c:-L2c;H2c:H=cH2 B. CH3CHECH=CHCH3 c. CH3CHQC=(T‘,CH3 o. CH30H=C|3CHQCH3 CH3 CHQCH3 D ,Consider the structure of 3-hexanol to the right, Which carbons are { _i'ii‘l-H—I “‘1 equivalent? ‘ CchchHCHchQCHg I A. i and a B, ii and iii (1. i and iii i 1‘ 1 1 l D. None. All carbons of 3*hexanol are nonequivalent i ii iii j :D Which of the following isomeric bicyclic compounds has the least stable carbon—carbon double bond? r. _... \ i z’ T ‘:= KT“ </ l 2 r]... v A_ \\/’ "'-~._.__,r'/ B {if} X.“- (/35! C \f/"AS'ECCL/ D_ L, Auk/x g Estimate the barrier to rotation about the C(1)-C(2) bond of butane. A. 0 kcaleole, there is free rotation about the C(l)-C(2) bond B. 3.4 kcah’mole C, 5 kcal/mole D, 66 heal/mole ...
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