30cfnlk - Chem 30C, Spring 2006 Final Exam Prof. Ohyun...

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Unformatted text preview: Chem 30C, Spring 2006 Final Exam Prof. Ohyun Kwon, UCLA Amng 04 Your Name (Please Print) Question Your poifits 1 (17 points) I r‘ ‘ \ 2 16 " T i ( pom s)__ _ i L) 3 (8 points) '— (a 4 mafia—mg)" . ,, 0 . h _ 10 i __ _ m 6 (8 points) 8 7 (27 poiat_5i_ .. . | 8(10 points’f ' ’l 9(16points) ‘ H9 10 (16 points) ‘ I L 1i (12 points) ll 12 (16 points)’ 7 7 | I L 13 (17 points) ' '0 Total (200 points) Page 1 l. (a) (9 points) Which of the following is a stronger acid? Explain why. @Hfll'g , Q (m deems —2 ammo so“: no @fl-fi 6 8n dam —9 Mam-chi —3 unthblc “ (i? rm“) k 1 1-. be hemmed-n. N no eadm SHero-fim (b) (8 points) Draw the pi molecular orbital (M0) energy diagram of cyclobutadiene. Indicate in which I: M'O‘s the electrons are located and predict the stability of cyclohutadiene in a very short sentence. We +W° MHYO‘K; exu’WM-S M 1‘1, ("A 1T} W‘bMI‘ld Nuke (\ldobu a WWW 0M3 W“ Uth 0\ QDMMD. “3 MMMMTL OI” Page 2 2. (a) (8 points) Several diamines are common building blocks for the synthesis of pharmaceutical drugs and agrochemicals. Show how 1,3—propanediamine and 1,4-butanediamine can be prepared from acrylonitrile. HZN /\/\ NH2 HZN m NH2 ///\CN 1 ,3-propanediamine 1 .4-butanediamine acrylonitrile Page 3 3. (8 points) Write Fisher projections of D-glucose and L—qucose. Hint: The following is the structure of B-D-glucopyranose (B—D—glucose). I I T I 10H D-glucose L-glucose Page 4 4. (20 points) Provide structural formulas for the products of each reaction step (a) O r\ E} m0 Hwy ,H+ CIVCOEEt 6) 1V5 9”“ O HCI. H20 firm La 67° ‘6 R iii“ In or. 0A0 I/"x‘CN HCI e 0“ H20 “I +10on H+ ‘ 2.H20 0"! J H2. Ni E H+ Page 5 5. (17 points) Show how to synthesize the following products form the given starting materials using either the malonic ester synthesis or the acetoacetic ester synthesis. [>—002H (‘0 EtOQCACOEEt 4-) x. MM" Noam : 1 km 1Map? mewHw LHULHzo 3 hem— Page 6 6. (8 points) Name the following molecules. @ ° 1:” \AH Cl COZMe —. PO W‘Jflfl U-Huombwum Fropcm —3,u~3TLk\mani\FLa_ pn Viva—3, u;— diokbm and all. 1,5 filiisornw‘ Y‘ntna‘ Page 7 '7. Show how each of the following compounds can be synthesized from benzene. Jug: “n wk (3) (5 points) H a: q HN03 0‘ NH“ {: 3 —3 —‘) RUB HLSOl-f Onflg wag (b) (8 points) OCOQMB F ems; _ e © 1/ «N01, 7. Continued. Page 8 (cl) (6 points) 8. (10 points) Rank the following compounds in the order of increasing Km. ‘ Smallest AW Wm flair—gESt—Xm _ l | | l. 1 Page 10 9. (a) (6 points) Predict the structures of the expected kinetic and thermodynamic products from addition of one mole of HBr to 1,4—dimethyl-1,3—cyclohexadiene. r, HBr '——I- —|- + Br Allyli Kinetic product Thermodynamic product (b) (10 points) Draw a plot of Gibbs free energy versus reaction coordinate for the reaction of bromide ion with the allylic carbocation intermediate in the above electrophilic addition of HBr to 1,4- dimethyl— l ,3-cyclohexadiene. Clearly indicate relative energies of the allylic carbocation intermediate, 1.2-addition product and 1,4—addition product as well as the activation energies for the formation of the 1,2-addition product and the 1,4—addition product. '2fo 00h f; elm: Melon Page 11 10. (a) (8 points) The following conversion involves an intramolccular Heck reaction followed by an intermolecular Heck reaction. Prepose structural formulas for the palladium—comaining intermediates involved in this reaction as well as product A. ¢ 0 + fiCOZMe Pd L2, Aggcoa ' CH30N W A UV¢/ \tlLul "tot PM. PdLal (b) (8 points) Predict the structure of the product of the ortho/para and endo selective Diels-Alder reaction between A (product from the Heck reaction above) and ethyl vinyl ether. Specify the relative stereochemistry of the chiral centers in the products if there is more than one chiral center. WK ortholpara~ endo-selective A + Worst Diets—Alder Page 12 I l. (12 points) Predict the structures of the products of the reactions shown below. Specify the relative stereochemistry of the chiral centers in the products if there is more than one chiral center. (a) \ / 5' 160 °C MeOZC/V HOW endo product (b) 98 °c / —* 0 CH0 O\//” PCy3 R ,CI u _ (d) o c" | —\Ph Y pcya {0.05 equiv) WNW CH20|2, 45 °c “9.0.9 Page 13 12. (16 points) List the following compounds in order of decreasing acidity. Page I4 l3. (17 points) Treatment of anthranilic acid with sodium nitrite and HCl provides an intermediate, A, that contains a diazonium ion and a carboxyl group. When A is heated in the presence of furan, a tricyciic product, B, is formed. Propose no. r -- s for A and B and mechanis - - he formation of ...
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30cfnlk - Chem 30C, Spring 2006 Final Exam Prof. Ohyun...

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