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exam_answers_Final_Exam - 01 5 t BoRlSovA EJ CHEMISTRY 237...

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Unformatted text preview: 01- . 5 t BoRlSovA EJ- CHEMISTRY 237 B Autumn 2005 Final Exam NAME What is the relationship of the two structures within each pair (a, b, c, ...)? Same? Isomers? What kin of iso u ‘ ‘7 mm D F 1: F HC F F CH 3\ / \ / 3 c c b) [email protected] and jg SAME H [H H ’H H H \ __H \ _H s E c) C=c=czx H and C=C=sz 1: A“ / / F H WM WDMWS h) \ cfi‘ Br and and and and “A Comsk‘f'wl'z'maé F t F\ /F Dimmer: C=C / \ Gwmdvtc Br. H IF ® SOJMQ H3C /C\H H Br \Cfi‘F WtoMW BoRtsoVA H F \ fl H F C \\\\\‘ Br \ C 6‘ Br CoMSH ELIWafl 1) and No2 N02 j) F3C—C EC—CH3 and H3C—C E C—CF3 Saw/M H \ /H k) aC—F and F—C 56”“ Br § wBr Br Br F djaAJeveo' 1) N and wkwmfimafl W StEéEL + RANAL Give the MAJOR organic products of the following reactions (Me = methyl, Et = ethyl.) and if the major product is a stereoisomer draw it in 3D. If a racemic mixture is formed, say so and draw only one of the two enantiomers. H H OCH; Br . \ / \ / a) C 3%, RAawuc c I? (3N1) /’5 Me El Me kt Ll each H H O \ \ b) C — Br __O_P_1”_> C "" H D 83‘ (3N2) D/‘C Me Me SIEG EL + RANAL Br / \ M (Addition) H e {4 Me Ev OH Cl I ’0; f) KOH (E2) SIEGEL 3. a) Starting with cyclohexane, make 02> O W O 1:] E00!» Li“ Pés‘ kv fin 5 0 Zn V 32::a ._2 .__.9 Row 1410 b) Starting with a hydrocarbon of your choice and KCN, make H Ev I 1 cu N + c) Starting with cyclohexane, make cyclohexanol. *In all cases above, you can (nay, you must), of course, use any needed inorganic reagents. F‘Iwfiwfitd Starting with an alkyne of your choice, make the following: a) CH3 CH2CCH3 {4-4— ”+4- Q43U41CEC/H ) 3 QszleCH I—lLo 6H b) \=/— CJ-k—CHLCECU‘JLU’IS H; Pt 0v LmbLMZ P4- LHL CECCH ————-a c) n-butane EDI/ex 632B Z-+ p6 Fvwdml’lval + Raoul Give the MAJOR ORGANIC PRODUCTS of the following additions to alkenes. If necessary, show the correct product stereochemistry. o H H+ 3) + H20 ———-—> Ca b) + HCl ———> CH3 H3C H H BY 0) >—-—< +Br2 (complete thlS formula) H CH3 Ev H trans CH3 2-butene d) + HCl ——-——> \‘/ Fvwdmi’hat 4” Rawmb a) In the reaction below, each product IS “parented” by a carbocationic intermediate. (6‘8) Underneath each product, write the “parent” carbocation (under each arrow) (1300616 éwae b) Write a mechanism for + (CH3)2C=CH2 —H——> (CHggc —CH2 —C<CH3)2 CH3OH | \c H 7‘ OCH3 CH: (Whizc :C’Hl @C/ (CH3)3C ”all“ \ ‘ _ H+ CH; CH“? 8470! ' ’_ _ 0443011‘ - 9" W C UL? ...
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