chem 2 - . (20 pts). Draw the structure of the expected...

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Unformatted text preview: . (20 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry, if the reaction is racemic indicate this. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. Br (CH3)3CO‘K+ A) Q/ . 1/ H 1) Hg(OAc)2, NaOH W "5 n g 2M B) >=f H9“ ‘ H WWW H 2) NaBH4 1’ Mr;va \/ , C) 0304 (Cat) fisc- S“ C n I” ’ H3 \ H202 MC" hm rikCt‘NwL CH2!2 D) \ ., zn'CU ' 7 {mgs‘mfl H H 1) O3 E) G Y‘ _ 2) (CH3>28 Y‘\CP\3 4’ if“ “j 2. (20 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistty, if the reaction is racemic indicate this. Assume all reagents listed are present in excess unless otherwiSe noted. If no reaction occurs, state ‘No Reaction’. F) HZC=CH2 )C'2 H v21 2) heat C? HBr ROOR l 1) Brz, H20 0 t“ mCPBA I) \ 9V /T‘\\\ .(1 eq.) OH H2304, heat l J) 3. (12 pts.). Show detailed reaction mechanisms for the following reaction. Include the structure of the expected products. 4. (12 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. a)...“ H 5w l l ’7 Z’ a if (I? A \ i 7 as L] PR 5. (8 pts). In each case indicate which proton is described A, B, C, D or none of the above. HC Hb Hd Ha R Hd A) Which proton has a chemical shift of 6 5.1 ppm. It forms aAfiioubled doubled triplet with the couplings J= 18 Hz, (d), 2 Hz (d), and 1 Hz (t)? : 3 '9]; B) Which proton has a chemical shift of 6 1.0 ppm. It forms a doubled t 'pled triplet with the couplings J= 18 Hz (d), 8 Hz (t), and 1 Hz (t)? 1’ ’ a n g 3 ‘9 l: C) Which proton has a chemical shift of 6 2.5 ppm. It forms a doubled doubled doublet with the couplings J: 16 Hz (d), 3 Hz (d) and 2 Hz (d)? flan: o r D 3 DB 6. (8 pts.) Provide the systematic names or structure of each of the following compounds include E/Z where relevant. c) (2E,4E,62)—3-ethyI-6—methyl- nona—2,4,6—triene \‘v’ . |—___._..._.__,,._., 7. (20 pts.) The unknown compound A(C3H11BIO) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. WhaiiscompoundA? HA mm + DHE 5 5 4 3 2H 2H 2 72H 1 \¢ {'4'\‘\“ \C. \C. \L. 200 150 100 50 o IR:3100,2950, 1750 andfingerprintcm‘l. HA: “he .3: Bar-(tn. 2mm) (an M H = \H-a 3: \GHL(°‘\:%“‘(A)' a": L; ‘Eg _m k ' B amt. ’U‘hfid) \ 3%.“) "‘\xf*\ ’2 3?‘ r H = majwzfizwawtu ' My} {*1 > C and. \HL H9: 1H -7 3: \GHLCA313HL(¢§\::H:? R rm 13 HeelHA‘SngthM1H7—w '\ ‘ WK? ‘2‘ *3”? I; \ 3V? R .u n ' r ' HL\CHa/Lfia I 543%: Hg: 3* CHer : CANS flE \ :0 i; 35% \D W. O :. Ame “65 m C05“)v%)‘1\‘}\kc‘n 2P5} gammak “sheila +£pr 2‘09}: i ...
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This note was uploaded on 07/01/2008 for the course CHEM 118b taught by Professor Lievens during the Spring '08 term at UC Davis.

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chem 2 - . (20 pts). Draw the structure of the expected...

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