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C357_Exam_1_Key_F2007

C357_Exam_1_Key_F2007 - Last Name[44 Z First Name ZEMCIB...

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Unformatted text preview: Last Name: [44. Z First Name: ZEMCIB J‘Cdé Z (Please print clear y!! ©) Registered Lecture Time (circle): 9:05 10:10 Cornell University Chemistry 357 Exam 1 September 20, 2007 Instructions: Read all questions completely before answering. You may find it helpful to first answer those questions that you find easier and then return to those you find more difficult. Please follow the directions for each question as answers that are not written where or how it is specified in the question will lose all credit. Good Luck!!! Signature: Page 1 of 10 1) (10) Provide IUPAC names for each of the following compounds or, when a name is given, draw the corresponding structure. In order to receive any credit, your answer must be written on the line next to each problem. Be sure to include any stereochemical designations, where appropriate. CH3H H H3 133$ mam“ B) grinning» tam H3C CH3 !0— excl-WI a8- QZM Jag—Atwfliy- S: (.9- WbflV(J9n/Fyi)‘#-frofy( Umflicamqe a; (gum / 17‘ - ame, / /0crc>[m\g E) Page 2 of 10 2) (14) For each of the following structures shown below, draw all major resonance forms for each. Lone pairs are not drawn in, but it will help you if you first draw them in. You must use “electron-pushing" arrows to Show how the electrons "move" from one resonance form to another and “resonance arrows” must connect the resonance forms. 0 of) 99 f6 A) “0‘15'90' QGQ‘é—EQ 6—? gift-OS (-3990,!)«09 0' 062 065 '0 B) / / fl #9 / \ 4-9 M CH2 T/fi’ 6 H \ C) ‘36, /\ l_\ :5 Q9 4/); a (9/6)“ /(}\€pé//\\ fl \ :9- 0? M 93%“) D) N"H @Nad ’\ \ 9< \/ 0 Z6 My,” \N’[‘{ M,“ 6 E) H>C__N+EN 1"" H>;%):Sp (—9 Mggfl/Org H H U H/ -_/ F) Avg/N {i=2 Aawgéfl’ Agfigfli/UM < \ <C \ \ CG) 06") w 6’ Page 3 of 10 3) (6) For each of the indicated bonds in each of the molecules below, rank their relative bond lengths (1= shortest, 3= longest). If there is a tie, write the same (and lower) number for each. For example, if two are tied for the shortest, label those two “1” and the remaining bond “3”, skipping number 2. If one is shorter and the other two have the same (longer) lengths, label the shortest bond “1” and the other two bonds “2”, omitting “3”. Write your answer on the line at the end of each arrow that points to the bonds in question. C) /_ D) ‘_::2_ E) Br F F) é/U _I_ ’/ _L \ A H Page 4 of 10 4) (9) The questions below refer to the following nine (9) dimethyl cyclohexane conformations, labeled A— 1, below. Please use the letters below each conformation to answer the questions that appear below. Each conformation can only be used one time below. Do not list more conformations than the number requested in the problem below. Hint: You would be advised to read all of the parts of the question below before answering any part. G H H I H A) Two of the conformations above have relative energies of O kcal/rnol. Name the two by letter below. 8 E l B) One of the conformations above has a relative energy of 0.9 kcal/mol. Name the conformation by letter below. H C) Three of the conformations above have relative energies of 1.8 kcal/mol. Name the three by letter below. ’9 C J D FL D) Two of the conformations above have relative energies of 3.6 kcal/mol. Name the two by letter below. F, G E) One of the conformations above has a relative energy of 5.5 kcal/mol. Name the conformation by letter below. Page 5 of 10 5) (12) Draw and circle each of the following cyclohexane compounds in its most stable chair conformation. If the chair conformations are of equal stability, write “same” under the conformation and make sure “same” is circled along with the conformation. O 9: Page 6 of 10 6) (10) Using “electron-pushing” arrows, show how the following acid-base reactions occur. /\ H O . I 0 ‘ ' H 0+ H H -o/ \o- B) + - Na OH Cl H H OH + “\\\H 1!), IIH + C) Na'OH + H-B' —-—> / “ + Na \H H \H i . 0* ___p I + H0 )K + /\ 2 H H 7) (4) Rank the following compounds in order of their acidity (l= most acidic, 5=least acidic). Write your ranking on the line below each. 0 0 0 0 O H F F 13% C1 OH A) OH OH OH H H OH H H Page 7 of 10 8) (10) Draw Newman projections of the following conformations, looking down the bond(s) indicated. If two bonds are indicated, you should draw a “double~eye” Newman. Look down the bond in the direction indicated by the arrow and the little person (meaning do n__ot tip your drawing upside down relative to the little person!). A) Page 8 of 10 9) (8) Predict the hybridization for each of the indicated atoms below. Write your answer on the line at the end of the arrow indicating each atom. 10) (6) Circle the following of each pair of compounds that you expect would have the higher boiling point. If they would have equal boiling points, circle both. A) . B) 0 ‘ /\ /\ t 7 L7 0 C)® X D) M W E) M G) F) O Page 9 of 10 11) (6) For compound W, shown below, compare it to each of the structures below it. Label each of the lower structures as to whether it is identical to, a structural isomer of, a stereoisomer of, or different from Compound W. Write your answer on the line below each compound. Compound W __ __ Wcfic—A Page 10 of 10 12) (5) Tetrahydrocannabinol (THC), shown below, and Nicotine (also shown below) are the active constituents in marijuana and tobacco smoke, respectively. Lighting plant material on fire releases (by putting it into the gas phase (aka. the smoke)) many compounds from the material. The inhalation of these compounds in the smoke of marijuana or tobacco produces the biological effects each is known for. Marijuana is often smoked in a bong, where the user inhales the smoke through water. Tobacco, in many parts of the world, is smoked in a water pipe (hookah), which also passes the smoke through water before inhalation by the user. Explain, in terms of chemist_ry, two things, First, explain chemically what passing the smoke through the water achieves and how., in terms of purity of the desired compound (THC or nicotine). Second, looking at the structures below, explain why (chemically! 1) it is possible to pass the smoke through water and still observe the desired biological effect. HO \ Iii / CH3 N O Nicotine THC i) EEWMS DQOiO/V EflFi’Ofii/UGIQ M Snug/Ce ‘SO/ULD/e fa luckier [byfrwtcis M> , (51> ROW (gym/{VS “4&157! [QQ i/V/QLOKAJL'? Qf/aobflq (r1007 "[70 (014/) )Lo ”071 grub/«re M 77% war/4.5,, M9 fags Wrw/A /I% / Eoo.n_n_n_2:o.>§>§ coEom :meagm qumSO 5:5 vommwooa “En. mé w..— v... is m... 5.3 A33 £89 8.9% 3. SN E 3n. az : an. 8 3 n «a 3 E3521 E332 in. 32555: r; . . . . . Né v.9 cod: . . mNKmr hm. 5—. n> to 3m mmEcmEcmr E. 3 8 E...E..u:> , . Eating E3325 MENU :63 E5 :2 a: 8“ E:__:=:.5 Eacasiz ad 63 0.... 3 Ezfiau NN 862 an. E Esp—En. No SN? mo mm Eamou mé a; SQ NE» 0... km 3 an Eigucfiuh E:_,—=E_w 1N . ‘ a; n... 9%.? SE . 2% $44 ww «0 :. om 3 5 «N R E:_=u_ow . E=_=u0 E:_=E_.r Eagflw md 5% m 2 5:3 m._. 8.8 .4 2 E=:_E=_< .mcofiwiufiu . EEmmwcobomm. 355:2. :2? a F . 3.5.3 E9: 952 we: vm m wme .m>< on 62:. 933+ «322:9» ml— 3 gonna—3m ucm .moazcmiu n gamma—c mm nanny: on 55: 3 Eu womqu omEEfi :1 62.5.0, .3qu .mEfim—u 925 2 u0u=32 .mo:_a> 33 En 05w: “awry—2m— mowumE 9.55.2 onEa>< w 2502 mEoEmm we.“ .6 2an 030.291 Embo§ was ...
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