Chemistry 3B - Fall 2000 - Pedersen - Midterm 1

Chemistry 3B - Fall 2000 - Pedersen - Midterm 1 - Dr....

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Unformatted text preview: Dr. Steven l’edersen Dctnber 2,. EDGE} Chemistry SB Midterm #1 Students Name 51:1]de Signature _ Tfl's Name at Secl‘ifln Number E H ;]{&t‘ Hung Pmblem 1 1 ['1 {2-1 pts} Problem 242:5;{32 pts} PmblemS 5? {13pm} Pmblemtl & {42pm} Pmblem 5 "‘3 a {3'3 pts} Pmblemfi '33 {54 pts} 1"1'I:I-‘t:1ien1'5r {lfipts} fl Tntal Pail-[ti {225 pts] FIEASE MAKE SURE THUR EIAM H A5 11 PAGE? NC} CELLCLJ Lfl'i'flflfi IMPORTANT: BE SURE TO ATFEhfl’T ALL PARTS OF THE MLlH-PAET QUESTIDHS SINCE MDT ALL PARTS REUIr ON A PREVIOUS PART FDR TI IE ANSWER 1. Provide one (and only one) real example for each of the following terms or, write a structure for a given chemical name (24 pts). meta-chlorobenzoic acid an anti-aromatic cation the LUMO of allyl cation (draw the actual molecular orbital) allyl iodide 2. Predict the product(s) from the following reactions. (32 pts) racemic mixture Draw the 4 possible products (these include stereoisomers) ammo—Substituted benzene with’a 130 NMR spectrum con3isting of 9 peaks Continued wk) heat -—-—-—-————> Retro Diels-Alder Br / . ———> H ’D Second order reaction 3. Match the molecules shown below with the statements (18 pts). ’7 x a. This very toxic compound can probably be found in your local compost pile. C1 ’“ b. Flammable "snow balls". H "r- (r c. Fragrant smelling shipwrecks. C L , /, d. After you hear about this molecule, strawberries never taste quite the same. l: ' e. The newest space fuel. f. “Hey, stop stealing my absisic acid!” said the host to the guest. “l can’t help it!” said the rr guest. “I have no more neoxanthin.” ' ,L I—, g. “Rats! Fooled again!” said the male bee to the orchid. h. The Mayan’s put bouncing balls made out of this molecule through hoops using no hands or feet! I wonder if Shaq could do that. A i. A molecule tied to both the Endangered Species Act and malaria. D "i ‘ polymer CI CI latex, rubber O O A Mixture of C21-029 alkanes/ O alkenes camphor 0013 B C DDT D Xe Cl 0 Cl F CIUOHCI E dioxin G CH4(H20)n H Lutein 5,6-epoxide 4. (42 pts) A. Patchouli alcohol is the terpene primarily responsible for the smell of patchouli oil, famous for its use in perfumes. What type of terpene is this? (mono, di, etc.): __ ' .43. ‘2— 8. Circle the isoprene units in patchouli alcohol. Be sure to include all carbons of a given isoprene unit in each circle. Mn N Patchouli Alcohol C. 8N1 solvolysis of patchouli alcohol and its allylic alcohol analog proceed at approximately the same rates, each leading to similar products. Provide a rational arrow pushing mechanism for Reaction A shown below. OH MeOH, MeO OH MeOH, M90 -..,, catalytic HCI “M -.,,I catalytic HCI Reaction A “Allylic alcohol” Reaction B Patchouli Alcohol observed OMe None observed D. Allylic alcohols normally undergo 8N1 solvolysis reactions faster than non- allylic analogs. They also lead to products such as the one that was not observed in Reaction B. Briefly explain why neither of these generalizations are true in t ' . . V ‘ his case Té‘“€ aléjglsc Mini/twat the}! v in“: s . “z. ( ' I ‘ J“ {‘ WA 9 ‘60 a“ 4pm OnC/(Cl/PM Cow (£06071, tar; time? '. U V r' A l m w, . I . ~., < l ,l .r. '» 1,: . “ NM 59. (wife {5% pt ac, f :‘n‘f’W’ w; gm :3’ l-v' Whit {Fawgq‘faap .. .‘ , “Mt/l3 tilt? 934’ WMRQJICQ act'l/ily 1% w. l U’ i it ~ 1 ~ «I Bil-l" “3 imam A: {big (hwy-t at” M ‘v‘ W?“ 5.; . Hexane extracts of a maple leaf at peak fall foliage were applied to a TLC plate and the plate was developed. The six compounds shown below were identified from these extracts. Two of these compounds showed up on the plate as orange/red spots whhoutanytype ofv$uahzaflon<fiherthan ones eyes. Labelthese compounds as VISIBLE. Two of these compounds were not visible on the plate until it was placed under an UV lamp. At this point they showed up as dark spots on a green fluorescent background. Label these UV ACTIVE. The remaining tWo compounds Were not visible to the eye 'or’under an UV lamp. Label these UV lNACTIVE. How would one visualize the UV lNACTIVE compounds? Circle the one that applies: / DNPH -rays \ \ ‘ \ \\\\\\\\\ \ii Si t 5. Provide the reagents (you do not have to make reagents as a separate step) and any other organic compounds necessary to synthesize the indicated product from the starting material shown. For each problem, five boxes are provided in which to place each step of your synthesis. No synthesis will require more than five steps. However, some or all, may require fewer than fiVe steps. (30 ms) 1 // ls ,A O ,, 1") M90 l M90 0 KM Kay"? 6 6. (54 pts) A. There are eight possible products for the following Diels-Alder reaction shown below. On the frameworks below, add in the appropriate substituents. Note: two compounds are already drawn for you. AG + W0 —-—->“eat OMe B. The ratio of (i) A to (i) B in this reactiOn is 5:17 Ratio'naliz’e'this’ratio using words AND any representation of the transition states you wish to draw. 7' . fllfl Hi ‘52:? {maizin 3} .3 -» t a“ .i; f“ ‘ u r1»: - “i y; . j; g 1",, 5 : a i ‘6 ’ A W . if * m «1" ti" 7 t V" . ' " I‘. lids/fl? ' "W3 ‘b t m u?) gm m }()0Fy’tf)5! %*r"”lwp w "pfl‘gi‘l‘lan SVAWDVL. ‘Mfflg P\ n d? (12$ ‘3 f; 1%” (7" (7‘ "'2 a? C. The pyrrole anion is shown below. Is this an aromatic compound? 165 Justify your answer by stating all of Huckel's rules AND by drawing the n-Energy level diagram for this molecule. Be sure to fill in the electrons on your diagram. 10 ' ‘-\\€\/V\M“ “- 6 N r \ I. ’z. do a flea ' v” Pyrrole anion I? \ I '9' @MZMQ. /€5 . (ON. of (mu? Valli; A M 7 ‘1 ill a 0; arms, n v .11.qu m M 0m 9??“ OHM 1i. All c M W“: 0~~(”‘r2:'ter5 D. The compound shown below is known as an enamine. Show two other important resonance structures of this compound. E. Draw the n-energy level diagramfor this molecule. and label the HOMO and LUMO. Fill in the electrons _ ow ——-- WW‘AD ND ULMD t "a @‘fi 5“ r (7, H “H; {m 'r‘ (3: fl .H— F. This enamine can react with methyl iodide to give three possible products. Draw the structures of these products. \J 3 products ( 11 7. (25 pts) A. An EI mass spectrum of the alcohol shown below was obtained. Two of the ions observed (identified as m/z) are shown in the boxes below. Draw rational arrow pushing mechanisms leading to these ions. BE SURE TO SHOW ALL NON-BONDING ELECTRONS AND lNDlCATE WHERE THE CHARGE OF THE ION IS LOCALlZED. In the boxes next to the arrows, show the structure of the fragment that was lost. ‘0 H :o’ @‘O/H 69- H electron \~ \ \ m/Z=125 m/z=126 - . fragment lost fragment lost B. Would you expect the ratio of ion A to ion B to be? Circle one: (513" B>A A23 Briefly justify your answer: . ‘7 3 A r“ t - ,i ' ['0 { g 21‘: T"? i“ {3’ / 0 V'\ A l (r, W\ Ail/(1:5 (’ C W of \FUKULiFflE I Wm E v ‘ /\\ bmfl Fwy/N, 1’49 f" QW x! Tim is iQE-Ot’“9m of ...
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Chemistry 3B - Fall 2000 - Pedersen - Midterm 1 - Dr....

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