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modern organic - Modern Organic Chemistry I Name SuLu TLQN...

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Unformatted text preview: Modern Organic Chemistry I Name: SuLu TLQN 3 Exam 2 October 13, 2008 l. (19 points) Answer the following questions on acid-base chemistry: (i) Rank the Bransted acidities of all equivalent protons on the following molecules (1 = . most acidic; 2 a second most acidic; 3 = third most acidic; 4 = least acidic): (a) E 2 bl 2—— 0 CH3 , H3C/ \H/ 2", poi-n+3 CH3 Z (13) 3 O HO g2 H Li PUM‘LS \IC/ \fi/ \SH‘ , 2 (ii) Which of the following are primarily Lewis acids (LA)? Which are primarily Lewis bases (LB)? BF; F803‘ H+ Br' NH; (CH3)3C+ LA is; LA££LA (iii) Formic acid (HCOZH) has Ka = 1.77 X 104. (a) What are the molar concentrations of the hydronium ion and formate ion in a 0.1 M aqueous solution of formic acid? (Just set - up the problem but do not solve for a final numerical answer.) ii") ii} Hi— L/s [1450;171:9511 )1; c 1.7’) x154?" ‘3 'I- a‘ H __ +3 ”60” ... '4‘ ° * mm] X +2 0.1-) 3“ x (b) What percentage of the formic acid is ionized? (Just set up the problem but do not solve for a final numerical answer.) 1) '3 ’25..» y)ao’)o 0J1“) 3. (10 points) Draw the Newman projection for the lowest energy conformation of 1- bromo 2— chloro 2— —,(l l—dimethylethyl)-1—methylcyclohexane along the C1-C2 axis. 3;“. lot!" (6411' 0k.) “i H CH3 5‘:le g}¥¢ (143:6 gr VS”: a: 2. (21 points) Write the IUPAC names for the following compounds as they are drawn. Specify stereochemistry where appropriate. (at) (55 ) ' 3 WW) I . / ’4’, H tl’” 4-1" m J" H ls/J/ (331F75}7-((m(;l~ ‘ LIMW‘U‘VL)” m/JLU (Lo V14. 4‘) p l l J L/ ix/ \V 4’ 4 I u \. __\( 7 {2 {Z Li S) " lub'on—o- l’firlfi IUF‘V Ll"Fl-\Auro- “1‘4"“? “cl-L |C\ {orniKhA Cl Ll I {L} 7 / I [C 4-4 47cm 5c55+3th4H+5 Name: 44 +l I J J J Fin—a r:_,fl (212) -((s)-:- LL10;0¢+L71)-J,:Iz,-Ilq fianalylficlobmj / “f 4:, fl +/ Wad- run—~94 Name: LL} 4. (16 points) Identify the following pairs of compounds as enantiomers, diastereomers, meso compounds, or conformational isomers. (a) Answer: (Ham-Pfomg/J Cl Cl H30 F F CH3 F CH3 ch F C] CI (b) . Answer: gong/Mo'k'gm/ I‘LW/S CH3 CH3 CH3 (c) Answer: Ev‘idm'l'rewf 5 Amy w“ , Cl ”’0! CI‘“ 0' (d) Answer: gin 34”“ch ’5 H H F Cl C! F H30 CH3 H30 CH3 on F CI F H H 5. (20 points) Identify one of the following two compounds based on its (representative) IR and 1H NMR spectra. Your first answer will be graded. [Note: 1H NMR peaks give as: chemical shift (theoretical number of peaks, integrated number of protons)] (a) C6H12C120 [DD 1'! HHSHII’TRNEEIEI m 2:: “DD EIODD EODI 1H0 1000 51m HHVENUHBERI -II ‘H NMR: 4.02 (16, 1H), 3.90 (16, 1H), 3.84 (4, 1H), 3.64 (4, 1H), 2.55 (1, 1H), 2.07 (16, 1H),1.86(16,1H),1.85(16,1H),1.68(16,1H),1.54(2,3H) (b) C8H12C1202 lDD 5D TIHNSHETTINCEIZI D . {HOD 3000 2005] 15m 1000 HHVENUHEERI ‘Il 1H NMR: 3.86 (4, 1H), 3.50 (3, 4H), 3.04 (3, 4H), 1.61 (2, 3H) 0 C) ' 5| i I] _ CIJCHJC'L-“C ._. C Jami—1504,» C] i an, EDD 6. (14 points) Answer two of the following three questions, each in 25 words or less. Your first two answers will be graded. (a) Do enantiorner pairs always have the same electric dipole moment? Explain. Yes) «I'LL MajWJch is {'Lz, Sam éd~ 9AA. 04766, How GV‘C Mi’rf“ r lug?“ o It: ‘Caxc La 9+1~¢f (b) Write the rate equations for first—order and second—order reactions and identify all the terms. l 5.4. (fin-[13: /< [A j ' J Fm‘l’e 37" [é [AJEBJ ZR cry/5,. [0: rev}? CW6 31"?!” Cat 3‘: C a hC-(‘h_£r‘m+;ofl “I R (0) Explain how Lewis acids and Lewis bases can be combined to form super (Bransted) acids. You may use a specific example or sketch a schematic representation. ochf . 0 2:25.12 .. sag a rscha ESE-$0” 0 0 ZLm-‘S «he! Lei—’13 508‘ Shbh cmjh‘r‘h 3“" ...
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