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Unformatted text preview: Return my exam in class Return myexam in Clark278 NAME Q (1 HOUR EXAM l 1. (10. 1 each) Below is shown the structure of an or of bonds in it. Some of the bonds have been indi different types of bonds described in terms of their letter. In the space provided on each arrow. wri letters are required. they may be written in either or more than once. cated ganic compound having a large number of different kinds with an arrow. Beneath the structure is a list of ponent orbitals. Each bond listed is designated by a te the letter that best describes that bond. When two der. An example has been filled in. A letter may be used G com :0: ll“ N : . \ _ / \ __ + i , —c c / \ \\\ H ' _. H N‘. e/ H + 12 A A. spa-s. c B. spa-p, o C. spa-sp. 0' D. spa-spz, o E. spa-spa. o F. spZ-S, a G. spz-p. c H. spa-Sp, cr J. spa-spz, c K. p-p, 0' L. sp-s, o M. sp-p. o N. sp-sp. c P. s-s, c Q. s-p, a R. p-p, r: S. 2 p-p. n T. sp-p. a V. spz-p, n W. spa-p, r: 2. (14. 7 each} in the space provided, wri following structures. Be sure ou use Br CHs—CliH-CHQ a_ CHacHz—C—CH3 /C|:H—CH2-—CH-—CH3 F—(fZH Cl CH3 a. Z' bm— 71 NM "‘[« ethyl— ‘54 te the correct lUPAC name for the compound having each of the correct unctuation and s ellin in our names. CH3 l— Hmme’W 3 -' Ll: Whom b1 Urdin Ll-isogmgyl— 1—Mel’h7l01cl0tlww Hour Exam I (a), Chemistry 301, Spring 2007. Page 1 of 5 pages 3. (7) Beiow is shown a contributor to the hybrid structure of imidazole, which is found in many antifunga. drugs and the amino acid histidine. a. (6. 2 each) In the space provided beside each of three of the atoms. write the formal charge on that atom. A periodic table is grovided at the end of the test. SHOW YOUR WORK. = 1 2 = "H RC. 5 hi > o N [ \:cifl___. F.C. (carbon): L{ —-(L{ +0) : O N: Imus-20> F0: ‘3'" (“H L) :2 ,1 b. (1) The formal charges on the remaining atoms are all zeros. Based on the formal charges you determined for the other three atoms. tell whether imidazole is neutral overall or is an ion and fill in its net charge if you think it is an ion. CHOOSE ONE. Imidazole is neutral. g Imidazole is an ion having a net charge of “ l . 4. (7) The contributor to the imidazole hybrid is repeated below. All valence electrons are included in the structure. a. (4) in the space provided to the right of the given structure. draw the structure of another contributor the resonance hybrid for imidazole. Be sure to include an unshared valence electrons in the structure you draw as well as the formal charge on any atom that has one. (it is not necessary to show how you determined the formal charge.) b. (2) On the given structure. correctly draw a curved arrow or arrows showing the electron movemei required to go from the given structure to the one you drew. +——* [Mg—H (other War; ()ossible) Irnidazole c. (1) Circle the phrase that correctly completes the following sentence: Relative to the structure that was given in part a. the structure I drew is aian contributor to the hybrid. CIRCLE ONE LESS STABLE EQUALLY STABLE MORE STABLE 5. (8) Draw the structure of any organic compound havmg molecular formula caH14N208 that include. a sulfide, an amine, and an amide among its functional groups. BE SURE that all atoms in your structure make the correct number of bonds as indicated by the symbolism you use. NHL 0 l Wamwm («43’5-"CH‘ZHCH'F 2"wa‘3 ( \Uij gossnitc > Hour Exam l (a). Chemistry 301. Spring 200?. Page 2 of 5 peg 6. (10, 2 each) The structure below is warfarin. a former rat poison which is now used to prevent blood clots in humans. Several of the functional groups in the structure have been marked with arrows. In the space provided on each arrow. write the name of the chemical family into which that functional group places the compound. REMEMBER: double bond, hydroxyl and carbonyl are not family names. a - t O 0 } arm mimic in (3 O / Cl / a u OH m 1 kid/LG. o 7. (10) To the right is shown a Newman projection for a specific staggered conformation of 3,4- dibromohexane as viewed from carbon 3 to carbon 4. H a. (5} Near the Newman projection is shown the H CHZCH3 1*! H beginning of a wedgelhash structural formula for the CHM; / same compound. The wad e bond on each C has CHacH2 Br _ (3 been provided. Complete the wedgelhash Br f structure so that it represents exactly the same 3 conformation as is shown in the Nevvman projection. WSW b. (3) On the circle to the right, draw a Newman Br. projection of a different sta ered conformation of U} 3,4—dibromohexane from the one that was given. a‘lzfl‘b 3r I‘llf Y 633% c. (2) Tell whether the new conformer you drew in answering part b is more stable. equally as stable, or less stable relative to the conformer that was given to you. Assume that Br and CH2CH3 are the same size. CIRCLE ONE. . more stable equally as stable less stable 8. (9) Below is shown one of the two chair conformations of a stereoisomer of 1.3.5-trimethylcyclohexane. a. (7) Next to the given structure. draw the other chair conformation that would result were the given structure to undergo a “ring flip.” WHEN DRAWING THE NEW CONFORMATION. DO NOT ROTATE THE STRUCTURE OR TURN IT UPSIDE DOWN. Be sure all axial and eguatorial bonds are drawn accurater in your representation. CH3 CH3 L33 w H H CH3 H- ) l 2aml at) H l astral 0&3 b. (2} Tell whether the structure you drew i more stable, less stable, or equally as stable relative to the given structure. CIRCLE ONE. equally as stable less stable Hour Exam l (3}. Chemistry 301. Spring 200?. Page 3 or 5 pages 9, (5) The illegal drug methamphetamine, known to cause brain damage. is shown below. The pKa for removing a proton from methamphetamine has been estimated to be 33. One possible base that we might try to use to deprotonate methamphetamine is iert—butyilithium. The pKa for deprotonation of 2-methyl-2- propane, which is the conjugate acid of tart-butyllithium. is 53. a. (4) Using the method described in class. estimate the equilibrium constant, Ken. for the deprotonation of methamphetamine by tart-butyilithium as shown in the following equation. SHOW YOUR WORK. H Li’ 9 N- u" -'N'- H " C”: + e“ a: ‘CH ,c-t CH3 CH3 3 D-Methamphetamine fert—Eutyltithiurn Lithium z-MethyI-Z-propane D-rne hamphete ‘ K. . [trivia >— infirm-bi ii a 2. (r to = to = lb b. (1) Based on the standard established in class tell whether ten-butyllithium would be useful for deprotonating methamphetamine. CIRCLE ONE: no. need a stronger base ‘10. (20) On the next page is shown the energy diagram for the steps in the reaction of1-propene with chlorine to give 1.2-dichloropropane. The reaction is shown above the diagram. along with the steps in the mechanism. Various features of the diagram are indicated by letters. Two letters designate the coordinate axes. five letters designate the minima (low points) and maxima (high points) on the curve. and the remaining letters show the vertical distances between various minima and maxima. a. ( 1) Based on the relationship between starting materials and products. what classification best describes this reaction? CIRCLE ONE: Additio Elimination Substitution Rearrangement b. (1) Are the bond cleavages in the mechanism shown r HOMOLYTIC? (Circle one) o. (16. 2 each) Below and on the next page are eight statements concerning the reaction. the mechanism given. and the interpretation of the diagram. Choose the letter from the diagram which best depicts what is said in each of the statements and write that letter in the space next to the statement. A letter _n"i_a_y be used more than once. Some will not be used at all. C 1) Positions along this axis correspond to changes in reaction progress. CH 0' H . . . E 2) The energy of the intermediate halonium ion 3\C@\C/ :5|:9 is indicated by this point on the diagram. H/ \H " B— 3) This point establishes an energy forthe reactants to which all other energies are then related by the diagram. CH3\C_c/H + Cl: a CH3\C§c/H-5l:e L 4) The awn”... for the reaction: H/ m \H H/ \H- " (i.e.. the first step) is shown to be strongly positive by the energy difference indicated by this letter. K 5) The overall energy change for the reaction. 159mm... is shown by this energy difference to be negative. Hour Exam | (a). Chemistry 301. Spring 200?. Page 4 of 5 pages i 2 6) According to the Hammond postulate. the transition state reached at this point should be structurally more similar to the products to which it is leading than the reactants from which it is formed. L 7) The activation energy. aGfi for the second step of the mechanism is the energy change indicated by this letter. Cl CH3\ /9\ Jib-re I! E 8) The activation energy indicated by this letter shows that the conversion of /C__C\ to ‘i—propene and Cl; is a fast process. H d. (2) Using the estimation method described in class. would 4.8" for the overall reaction most likely be positive, negative, or appro ' ater zero? CIRCLE ONE Strongly Negative Approximately Zero Strongly Positive CHa H 'i' ?' Overall reaction: \CZC + Cl; CHE_C_C__H H/ H is; i-ll 0 1 mid {W a 53 < 0 Steps in accepted mechanism: fé} : CH H Cl 1) “egg” ——- CH3\C”§\ /H 19 H/ \H H/ \H h Hour Exam | {a}. Chemistry 301. Spring 200?. Page 5 of 5 pages THIS PAGE MAY BE SEPARATED FROM THE REST OF THE TEST TO BE USED AS SCRATCH PAPER 1 17 18 1A TA 8A 1H 2 13 14 15 16 2113 1.000 2A 1.000 4.003 . 9 1D F Ne 10.00 20.10 1 I -' Cl Ar Na 9. 3 4 5 6 7 a 9 1D 11 22.00 24.01 3B 43 5B 63 TB r———BB——_|_ 15‘ 2B 2000 2000 3007 35115 39.05 1 1 I a 4 t 5 ? ': I: c 5 S K 3c TI V Cr Mn Fe Co NI Cu Kr 301.10 40.00 44.00 47.00 50.04 52.00 54.04 55.05 50.03 50.71 03.55 05.37 00.72 72.50 74.02 03.00 B I 1 ' 'l ' - ' ' - . 1 I. . . . 5 . ; . . ' . Rh Y 21' Mb Mo Tc RI: Rh Pd Ag I I KB 05.47 07.02 08.01 01.22 02.01 05.04 00.01 101.07 102.01 100.4 107.07 121.7 127.001.25.00 131.30 .; i. - ' 1' . :1 1 '1 ': .- . .. Cs Ba La Hf Ta W Re 05 Ir P: Au Hg Ti Pb BI Po At Rn 132.01 137.34 1:10.91 170.40 100.05 100.05 105.2 100.2 102.2 105.09 105.07 200.50 204.37 207.10 200.05 {200: a? a 0 -'- 1 ' 10 0 {2101 {222) 1. 9 Fr Ra A0 {223: 220.03 [22?! 1261] (262) {263) {202} (255} 12061 ...
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This note was uploaded on 03/21/2010 for the course CHEM 301 taught by Professor Morrow during the Spring '08 term at New Mexico.

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whalen1 key - Return my exam in class Return myexam in...

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