Yangchem140Aspring06

Yangchem140Aspring06 - Chemistry 14DA NAME[please print Am...

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Unformatted text preview: Chemistry 14DA NAME: [please print} Am Mgr“ KB Professor Jerry Yang First Last Spflfi, Final Examination June 15, EDDIE Signature: PID #: I give Professor Yang permission to leave my graded final exam fl post my final grade for the class by PID number on the 6‘” floor of Pacific Hall: Signature WRITE YOUR NAME AT THE TOP OF EVERY PAGE! USE NON-ERASABLE INK ONLY! Write the name of the person sitting: To your right To your left Please check your section number: M W 3-szsaPM A? F s-s:soPM A2 W 4-4:seeta as M asset-Ital As Th 44:50PM as M 5-5:5flPM A4 Th 5-5:sthM mo M assume as F ts-s:soPM A11 Th 4-4:5oPM A5 F 4-4L5UPM Other {please explain}: DO NOT OPEN YOUR EXAM UNTIL YOU ARE TOLD. Please write the answers you want graded in the space provided. Do scratch worir. on the backs of the pages. The test should have 14 numbered pages. lCheck to make sure you have received a complete exam. A good piece of advice: Ftead carefully over the Questions at least twice: Make sure that you understand exactly what is being asked: avoid sloppy structures or writing. Good Luck! DO NOTWFIJTE BELOW THIS LINE l. {1 a) v. (15} 1x. {as} it. {so} vi. [24} x. {13} ill. pa) vii. (24} iv. {16} VIII. {as} Total {20D} I. [16 points] NAME: {please print} First Last Name or draw. as appropriate. the following molecules. Please write your answers in the space provided. Indicate stereochemistry where necessary {i.e., cis, trans, Ft, 5, Meso, etc}. You may use condensed notation. or line diagrams for your drawings. ND FISCHER PROJECTIONS! a. Provide name ofsrrucmrs: moi shit-09E iIme — LAP iii chi-tired; tic-Jii'ocio 43M Draw a chiral compound with the molecular formula {341150. Show stcroocitcmistry explicitly. Draw two diasiereomers of [4.4.D]—bicyclcdccanc (Draw them in their most slabie chair conformations} It. [so points] NAME: {please print} First Last a. Draw the two most liker products for the following reaction in the spaces provided (Hint: product B weighs one gramrmole more than product C}: E {major} C (minor) b. Draw a Newman projection of the conformation around the 03-04 bond of A that upon reaction with NaNl—lg will lead to product C. Put 1,rour answer on the template provided: T t %r i CH} H c4 cs {it C H ' o c. Draw the major product {in the space provided} of the reaction shown in part {a} it we were to react molecule A with NaCN instead of NaNHg (Make sure you show stereochemistryl}: III. [15 pcints] NAME: {please print} First Last Fcr the fclEcwlhg structures, indicate in the bcxes whether the mctecules are chiral EC} cr achiral {A}: sea a he: is Ci W. [16 points] Draw the major cctet rescnance structures {Kekule structures are also UK} fer the telicwing rhclecules. Show aH Icne pairs cf electrcns and any terms! charges. Kflfifififir {w e _“1. .6 NE) c :_ e, . [H cue} E - L ..4' 0.‘ 2 2 MC (far? klrcr‘R’L; .: ,I 3 ' H; .3 . )1: Unfit? 43W“ HN02 E rg-rUf-Q‘ War u,«— R E) :U: U. [15 points] NAME: {please print} First Last i] Supply the major organic presume} in the sexes previded. Indicate stereechemistry where necessary. ND FISCHER PROJECTIONS! ii} If no reaction assure. write "no reaction" in the product bex. 3' GT3 xBr 1.“?th N30 H3CD|"'“" DMSD Br 1). DH H 1‘: S O; OH _—-.. 130°C (1. 31 BI [I —'... VI. [24 points] NAME: {please print} First Last Provide the missing structures in the spaces provided. Show sterecchemistry. where known, explicitly. ND FISCHER PROJECTIONS! (Hint: it is sometimes helpful to work oaciiwaro's from known structures} csHtoDs GaHaD CiHmD CngCI an opticain optically active optically active optically active inactive diel I} t} CHSMQET 1} FCC D 2 H+ H» 2 CH Li 3 l i :0 l s 3}H_IH20 All 3 alcohois are constitutional isomers I of each other HBr Her Pals i--- Both moiecuies are constitutional isomers of each other KUClCH3}3 LiooH3 JL/ VII. [24 points] NAME: {plaass print} First Last For the foilowing pairs of reactions. mark an "X" in the box on the right indicating which will go faster and circts the mechanism corresponding to the given reactions. 3. Hal 1 Br —- D Acetone Ha] I + KB” 5 Br Acctonc circlc ntccltanism: @ 55.1 E2 E1 1}. NaOCI—I5 CI —"" + NaCl CHsflH + o CHEDH circle mechanism: SN: SNL 62) E1 E. Br Br H o D Br/b 3 HID/b + HBr r '3 oH “<3 WE E —II- circic mechanism: UH. {cunt} NAM E: {please print} First d' £32 + CH3BI fl, gals? x” “x. ragga” + CHBBT Mclhancl SEEP x” “M. circlc mechanism: 3342 55-1 E2 E1 c. OMS A “3504 A —-'- 13ch \ 0M5 “1:30 )\ —"'d 4 A 1300c circle mechanism: 1‘ c CHgflr 4: NaPMcE /U\ CHgPMcg .—'... CI CH3BT + Nat] A CH3C1 —- circlc mechanism: f. 5N1 E2 E1 + L331 Nu Br NEIBI!’ ED ED E El VIII. [23 points] NAME: {please print} First Last Supplyr the missing reagents needed for the following synthetic transformations. When the reaotion oonditions require agueous workup, it is not indicated. Indicate only.f one reagent per box. It the transformation requires more than one step (aside from aqueous workups}. separate boxes are provided. OH DH 3. + —l- {DTI = triflote} b. 2 :3 O o PCL, r-nunII DCIH3 (3. Br kH 20H d. \i W (rasemio mixture) VIII. {cunt} NAME: {please print} 1‘ 13 * . r) mi 01“ L1 3} '3' ME” g. D 1i} First CI 3: \ Last CI IX. [23 points] NAME: {please print} First Last a} Cyciohexane carooxylic acid undergoes free radical chlorination to give some miner diohlorinated products, two of which are Aand B. Using the following table and the cyclohexane stencils provided {cation #1 is already.r labeled for you] , show the structures of the most stable conformers oil: and B. For each, calculate the free energy of the ring flip to the less stable conformer. CI- OH 0 OH mfikfll + + others cyclones-ape; carboxylic acid El A B Difference In energyI between axial and equatorial substituted ayalahexanes {kcal mol") Suhatituant sl-l gq-six Substituant sl-i “r, u H o F o.ss CH3 1 .? Cl [152 CHacHE 1.?5 Elr {1.55 {CHS‘JECH 2.2 l 13.46 gHHlijrac 3 rs EEOH {113? Hzfi 1:4 CDDMe rise Answer: L1 ; ei Most stable m 5mg conformcrs of a and B. l Li it A B oatmegfies : Hal arr (anthem: Her locrahasegjitflrSJ—i 1mg,an smock AH Lo less stable conformer [Kcal.-"mo1e} 31H: +0337” an: +ZJLf§ ll ix. {cont} NAM E: {piease print} First Last h. Consider the following equilibrium: 1*th nirnn gimm- D?- D: Circle the correct answer to the following: i) The pits of the carhoxtrlic acid group in molecule A is glows?) or higher than the pha of the carhoxyfic acid group in molecule B. J“ ii} The Km of the reaction is iess than ,Cgireate@, or exactlyr equal to 1. ._____ iii} The aH orthis reaction is greater than , iessthh’a—fi, or exactly equal TD ZEN]. c. Viagra is a potent and selective inhibitor of cGMF’ specific phosphodiesterase type 5 {FEES}. which is used to treat male impotence. Circle the correct answer to the following statement: N \ _ /N Viagrahas®L 2! or :3 stereooenters. 1rIr’ittigrt'i {Pl‘ixcr} 12 x. [13 pcints] NAME: {cteese print} First Last The tclicwing is the structure ct Calicheamicin yt, an extremely pctent antitumcr agent isclated from a bacterial strain grcwing cn e rcck in Wacc, Texas. ME OMB as a @503 on D Caiicheemicin y1 a. Name the key functionality fer each of the circled grcups {A—G} in the structure ct |Caticheamicin: A: Alkgfli E: gritty! Milieu“ mil—mi EL (:1: Ariana G: fig. ear“ D: kflj'n-E 1:. Write the ccrrect answer tc the tciicwing three statements regarding Ceiicheamicin: i} ch many sp‘? hybridized cerccns are there? Jr 9 ii} ch many seccndary alcchcls are there? 9 iii} Which grcup has a higher pitta! functicnat grcuc B cr E? B 13 Periodic Table artfaf '14 ...
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This note was uploaded on 10/17/2008 for the course CHEM 140A taught by Professor Whiteshell during the Spring '04 term at UCSD.

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Yangchem140Aspring06 - Chemistry 14DA NAME[please print Am...

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