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FA02 MT1 - CHEMISTRY 140A NAME(please print A W“...

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Unformatted text preview: CHEMISTRY 140A NAME (please print) A W“. bji‘fi ; 32 Q 3 MIDTEHM EXAM HHS LAST OCT 22, 2002 . szemwnegflaflw ID NLMBER 335K133 0‘30- \ LASTNAME 0F PERSON mama INFRONT 0F Milk—LL MSTNAME 0F PERSON SEAIED BEHIND YOU: Q (3 €, farm (.3 DO NOT OPEN THE EXAM UNTIL YOU ARE TOLD TO no so. — Please sign your name on the top of pages 1 through 7. — Piease check that you have 8 pages (including this one; page 8 is blank). - Answer only in the space provided. Do not write answers on the back of a page. Question Points Score 1 15 1—1/ 2. 15 AL 3. 18 3 4. 22 Z 5. 15 JL 6. 15 A Total 100 3:72 H He Li Be B C N O F Ne NaMg AlSiP S (31331: K CaScTiV CrMnFeCoNiCuZnGaGeAsSeBrKr RbSrY ZrNbMoTcRuRhPciAngInSnSbTeI Xe CSBaLaI-IfTaW ReOsIrPtAul—IngPbBiPoAtRn NAB/law la. (4 pts) Circle each of the following compounds that have connectivities with all singly bonded atoms and no rings in their structural formulas? 1 t . I l . H .g _. _ - _ AA c.» ' as s: a t e e"- “9 LE C14H23C15 @ H C‘ 9.0 45’; Quota—1+er TcN‘a JMW 1b. (4 pts) Draw a three-dimensional Lewis structure for each of the following compounds. '9 Liz; For each structure give the hybridization for all c, o and N atoms. Show all nonbonding M flaw“ electrons. Show formal charges. 3 7} (a) [HZOCHJEBI‘] _ (b) [NHJCOsH] _ - 4? ul— 4 CS. t .. ez/ ‘ . a €23? ' H / {Ema I, * / H . . V . . . 3 , , x '3 \ \ _... g, - W— ‘ijd £0] aye) ~59 maimed e: ”$1 $3; 2. 0.5 _ 53:93. la. (3 pm) The four carbon atoms indicated in the compound shown below are expected to have very different electron densities. Predict the relative order of electron densities around the carbon atoms labeled A, B, C, and D. List the carbon labels from left to right, with the carbon of lowest electron density on the far left and the carbon with highest electron density on the far right. ‘5‘ ,CH3 f “xi? {up (I) \x (,CHgCHgO— —H D m ... c_- or 1 _ ( CH20H20H20|® fit), an 0 I <5 C r I .0 é- ld. { 4 pts) For each of the following compounds draw a three dimensional struht‘lire of the molecule, show all nonbonding electrons, and give the hybridization of all orbitals that contain nonbondjng electrons. You need not draw the orbital for the nonbonding electrons. 5 31,62 9 - ‘0“ CH CH-(':h "" \‘M HOCHZCHZCN 3 — o , 6? a a a. (y l V __ k s a P , . W _. C .— c, 1N . c;:% an ’4 V at \ I “w? H ,C— lr1 \ between atoms, except in (II-I3 groups. a) 4(7) C a A Ex, M 3 c- __—"' - / \ —'\ A" ’0‘“ H30 jot/H ig—H “2C (3’ "t. H *‘ H H e ‘2‘ ugC. Q cfia b H3C\ /CH3 \C/ ) (‘2‘ 4 “l\"6 EV H—Cl: g . ‘ C 3 H30/0\CH3 “EL Elna 3b. 3c. NAMEMjQA/gmé— ( 6 p13) For each of the following equilibria, indicate over the reaction arrows whether Keq will be “> 1” or “< 1”. You should not need tables of pKa values to answer correctly. a) KW “WW C154 H G) CFLCLH H / + 0—H + H20 3 H H '6) we boas. caelck b} ?H G) Iris-)foH + NHCHa NHgCHg H MIX basta— ehcw “C3 ) r 015'} C i? h e ch/ROG + HOCHS 0——CI-l3 ‘0‘.le 95 cm. A K c mesa (6 prs) For each of the compounds shown below draw two resonance contributors and label each as either “MAJOR” or “MINOR”. Show formal charges. md5o( Mk‘m (— a G> n’YL‘; 'firfi" :6, f f: BF3 a, \b/Y: '- “$541) 1 g j” .11; Mid K rte bar a} (6 pts) For both of the resonance structures shown below, draw in all formal charges. Below each structure draw a resonance structure that is a more important contributor. { Old/D I. /,O.: E) eta/$259 H—o= , *~ m, ” " GD 9'? H p\ ,Q, NAME: AM: i t gmbflc (6pm) For each of the following compounds draw the structure in three dimensions (except for methyl groups which can be shown simply as CH3 or Me). For all n-bouds draw in the shape of the atomic orbitals that give rise to that tut—orbital. Be sure to clearly Show the orbital directionality relative to the positions of the sigma bonds in the molecule. . E) CH N=NCH k 3 3 “30 NH:9 4b. (6 pts) For each of the following compounds draw the structure in three dimensions f"? (except for methyl groups which can be shown simply as CI-I3 or Me). Draw in the shape of the atomic orbitals that contain the nonbonding electrons and indicate the hybridization ‘5 of the orbitals. Be sure to clearly show the orbital directionality relative to the positions of the sigma bonds in the molecule. NH2CH3 pH3 CHaNHe ”‘7: . 0:; A59 I We " {Iii-HM / “1H Me‘I-IJ‘Q' H’ H A {L ”2/ K 4c. (10 pts) For the sigma bonds that are drawn in bold, indicate the hybridization of the atomic orbitals that must overlap in order to form the sigma bond. For example H-H would have a sigma bond that results from s-s orbital overlap. _ ________'M__—'_—_-—-———————_—_- ' 5a. 5c. 5d. NAME: ~ ftp” (3 pts} Draw a single energy level diagram that shows the relative energies of o; 0*, 71:, 15‘, and nonbonding (n) orbitals. Be sure to label each energy level in the diagram. (6 prs) Draw an energy diagram that shows the relative energy levels of 7!; 111* and nonbonding (n) orbitals of formaldehyde (CHFO) in the ground state electronic configuration. Then draw the related diagram that shows the excited state eleCtron configuration which results from a rrto attexcitation. ground state excited state (2 pts) Which would require a lon er wavelength of 1i t: a (7: to nil) excitation or an (n g ’5‘ . . tOTC )BXCItatIOD? W fl ._’-:3 CT< ’71 Emiwfi m AV 2“, ( 4 pts ) Give an example of an addition reaction that works for an alkene but not for benzene (C6156). Draw the structure of the starting material, the reagents, and the products. Do not show the mechanism for the reaction. 6e. 61'. 1); E RH! 6c. NAME—WM (2 pts) What is the strongest acid that can exist in aqu us solution? an 4" 31¢ ( 2 pts) Draw the structure for an isomer of benzene at is expected to be much more reacnve than benzene. (19, H U 1 ’1 is _ (Li—“r— C:- “ ?* " C?— d) g . (2 pts) Rank the followiiti‘g- compounds according to the length of the indicated bonds. Shortest bond on the left. Longest bond on the right. CchaéH, among—(3H3, CHEQHCHS, On A B c D L %;<_Q_<_§>_<L (2 pr) If the change in standard free energy for the transformation of A and B to C and D is +1.0 kcallmol, will the reaction f , d B give any C and D? _ #2:; gm (1? ( 3 pts) For the generic equilibrium sho below, what will happen to the concentrations of [A], [B], and [D] if the concentration of B is increased? What will happen to the value of the equilibrium constant? A + B _"—"" C + D w KejL-r mi“ Shot-k ”TL-Q w mngQ‘a/x (a m- 4% LC?) ~W. t ,i <- crmm 2% —~- Mg; 666:3. f93~x 1:“ H 3K ( 4 pts) Prowde a rational for each of the followmg statements. 4. a 0-. ‘CFLQH is not a typical alcohol but rather an acid” 4"— EACEJQJ . Ewe— ; r- ‘. - . I “CF3OH is of surprisingly high volatility” Ge 3 much lower boiling point than expected) aka, OH' ‘1 ‘cxxi “(was fin: N“? 6.323%15 {user gar-an??? \Qerchng-c a5 {do-s “1":79/15 ...
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