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Chemistry 345- Zimmerman- Exam 1b- Fall 02

Chemistry 345- Zimmerman- Exam 1b- Fall 02 -...

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Unformatted text preview: k:;fi1”1£f‘Ffifiiq Organic Chimistry 345 Nani {Pluasa writi Cliazly} Fall EDGE Exam 1b Student ID Eaur Home Town [as in UN RecordSJ Quastion Paints Gradnr’s Initials 1 U . [“5 2 ”'2 .- _ " 6—5 a S" i5. 4 M if [email protected]_ 5 E? _firf_ 5 20 I _A‘T'_ v 5’ 1' fl 3 ' 5 5 fit. 9 l 0 12A 10 (E? E5”— 11 F : EH” 1% «as; 12 - 2 organic amines 345 ‘1 I 4‘;— _Fall 20D: Exam 1b Hams {Plumes firita Clearly} 1} Give the products of synthesis as isolated after gorkup. i2 Points each] dd EHN g 9 +2_a- Cyclohsrsnonc + Ethylene Glycol H+—l- (j .1. '13- BsnzyIfiAlcohol cooH G (Jones' Reagent) (It; (31133, H2304! Acetone f‘szc :B cocH . - - —————————;- romeo-1 -+ c 1) Mg,Et20 <3) ‘5' 2) co: 0 All I d. P“ ”m" Aqueous NaOH l1} . Methleenzoatc —|- Phat .a + HUME. reflux (heat) 0 + 15' & ma 6 D c D 0 {— 2rr. NaGN. stoH M” Hose “J 2] Draw the structure for furan putting in any unshared electrons present. Then decide whether furan is aromatic or anti—aromatic Emmafir. [whiChII . Totally. including pi bonds and unshared electrons. you have a total of g . Nevertheless, furan fits the Huckel 5&4“; rule since a (give number) unshared electrons [are. part of the pi system. [5 Points for each mechanism ' question] X4 £11.. roI‘I‘.’ 'Tf 33. Give the mechanism for decarhcxylation of a B-ketoacid. Use PhCEOJCHzt‘JDUH as your example. Draw your arrows carefully. Put in all unshared electrons and any fennel charges. ECHMJISM C? D / c- c: . B H H F. 3 ‘ _ 3 -C..{ C 3(‘33 H'E'LHJHéE-J‘ElH Phififlf—H; I (”:3 PL H: ‘r E J 4} {A} Using the Frost-Musulin Circle Mnemonic given for the cyclcprcpenyl species... Complete the mnemonic {Note: Energies of the vertices'are given]. fill in the electrons corresponding to the stable species. Finally. get the Pi-energy. For part B, get the energy of the non—resonance stabilized species with isolated double honds bonding and antihonding MCI's with the proper number of electrons put in. Then add to get the Pi energy.[lfl Points total for this question] H A: E: _._.— “ “ti-H *‘"1-_‘1h-. +1 —._F+1 -2 Pi Energy = 4:! Pi Energy for the Ethylenets] = ‘Q - C: New give the Resonance Energy {DEJ for licenses in units of [fill 33. EAT. Ir: 1' .- :-|p.i.r.-.I I organic Chemistry 345 Fall 2092 Exam lb Name {Fla-ass Write Clearly} 5] Encircle each of the aromatic species and underline the anti—aromatic ones [5] 'OOaQOOO. @ 6) Give the pgiducts of synthesis as isolated after workup.[2 Pts Each] I Lflacfifi unwr- fi’ 'flfa Ethyl Agetete + Methylmnine —:-— (HHS-Lit MHML Jr} b. Paging Br: if? ' Acetophsnons —1- Ph v r; "(T H.1 inn I-[Br Cal. sr C'JI-f @ I P (.CJDEt Jr'lre. Egflfa'mwe + BrCHzCDfl hm} anbemne hflHLHh d. -- 471/ Amhne W'- © 1/ a" ma * é Ph3P=CH2 cH D at. e | +3, f mince —> are + Log 3}. (about 111] deg} C? '3 fir. 1. 9 ME CH CH CPD '—PMEDH . + = _ I“ 2 CH3 NaDH o D s were} fi +2., h' Acetophsnone W PthH 4' HLIS Q? a CH} LHJ'r'. (,1 @ +11. Toluene + AcetY'Chlflflde Alma PhNDz fi’ 53 g1 terms or cage—o-t-ug o4 CHE-H 5' l 3 5 ” + as ioH +2, j.a.cetic Anhydrifie + 2-Propancl 2:- :HEL- OCH We; 3 ?] Write out the reaction mechanism for electrophilic substitution of Anisole by the electrophile Br*. Show the starting material.r the sigma intermediate and the final product. Write each structure clearly with all unshared electrons and formal charges. In the case of the sigma interme_diate, write the most important resonance rem; . =oMe structure.[5] gnu-gar Er E, C *7 “t" 33 Give the mechanism of the reaction of the hrcminaticn of Anisole (include the structure of the most important resonance structure of the sigma intermediate and also the final product. You can simplify with the attacking electrophile E+heing written as a single bromine with the proper charge and number of unshared electrons+ [5] Organic Chemistry 3&5 Fall 2002 Exam 1b Name [Please write Clearly! 9: Give the products of synthesis as isolated after workup. [2 Points each] flcfl Met} a‘ Li, t-EuClH %! LM.NH§ Met} m 13- CH3 on 5 4T? 39% QoHngoH _.—u— is a r. H c. FCC, CHECIZ g. ”'L'“ pL-E‘EI‘: 9.3“ Bonzolehlorids + show ——+ a H : Fin , Ph H Ph-c=o —a- PKCH CH ‘3 i3]... (3:0 + \CHE CohoNsDH F'L-{li-c'. more fi’ LE. Benzoyl Chloride + Ethylamlne Fir L- N H 5%: a nme 93 eczema cs: "' g. D mil-1L: w Cb we HC] .5 Cl C: h. 5“?" \é/ D 3 : D20, has: fie mm m” L I Ihenzme 4 - —I-- ‘V 1 supra” ooze @ c 10] Give the Mechanism for the Fischer Esterication of Benzoic Acid with Ethanol. Include the Tetrahedral Intermediate drawn explicitly. Draw all arrows carefully, put in all unshared electrons and formal charges throughout. [5 Points each for all but one of the mechanistic questions] eflréH EHJDH 0 “a?“ a (:3 _/' 1 - ' i..._._‘:_:;. ‘flfl/ ‘r CH;£H3 '#% -=A~D‘LHffl3 ~ DLHALH: (J. r llllfiow many absorptions are anticipated in the 1H NMR spectrum of each of the 3H3 following? {a} l,¢-Di-t-butylhenzene Q ; [b3 Ethyl t—Eutyl Ether 3 ; (c3 4-Chlorotoluene 3 . (NOTE: We are talking about entire peaks, not splittinq][5] m LH {H:GC.[LH;}|:, 3 gifl The Huckel Rule requires fity+a (fill in] electrons for aromaticity and is” r sntiaromaticity. [5] ...
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