PracticeExamI_2005

PracticeExamI_2005 - DRGANIC CHEMISTRY LAB 3H9 NAME EXAM 1,...

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Unformatted text preview: DRGANIC CHEMISTRY LAB 3H9 NAME EXAM 1, EMS TA Please write eiearly and ansWeI' the questions direetly and eoneisely. Partial credit will be given where appropriate. The total number of points in this exam is St). Total seores will be multiplied by 2 to obtain the final score out of 1m pts. 1. [5 put) Write a detailed meehanism for the following reaction of phenol with sodium hydroxide. Rename the reaction in the space indicated, and use appropriate arrows to indieate eleetron movement. indicate ml fonnal charges and non~honded electrons clearly. DH ONE Kat-t + NaDI-l —“——-— + H20 lWrite mechanism here: Q in. 1 I '- ttju 'H 0 won flak ., l @l l I: :7 lo * “WW 2. {5 pts.) Write an expression for the equilibrium constant, Keq, of the reaction in question 1. The pl‘La of phenol is H13, and the pKa ofwateris iii“. 1_¢.-'Jllll_‘ll'l(-Q_q : S"? " .0 ‘72:) \ Kl 3. (5 pts.) Phenol has a moleeuiat weight of 94.1 and a density of 1.3? gme Write an expression for the 1rolume you would measure to obtain 15 mmoi of phenol. Indicate the units of your answer clearly. .1 UTA “ff-l t1 :— fl‘t M) :t LP-J and 4-. {ill pLs.) You are given a mixture of the two compounds shown below. Compound A is not readily deprotonated in aqueous solution. Compound E has a pKa of about ll}. Describe a complete procedure that includes a single adaption, which you could use to separate these two compounds and then obtain them both as flight Be Sfllfic about your choices of solvents, reagents and procedures. 0 Cl Compound A Compound El : Us“ N/cefl HEL. : .lzl..‘_‘~_M/cea \. Catt-ties. iaa alt-tildes takes . r Treafilill‘ t; cs fiwtttaktrfl $~“-‘fl.T‘-b\ file-“x er-tllr’e-k at. l m amt Wash gilt-l,“ :5: g [yiqfig {gig fix; kit-[Elk '5 {o W-dk‘n'ifi‘i l -Fi"- Ill-:3, “Tn-Q ’2" U‘ “VIP pk (alt-(L3 "LAFE'RGT ET Te. Joke-Etta. ‘39] “.5'1T.Qe1ae}\ A « 4”. 3M H it‘ll-Alter. l}. regimental. “A l’tfim 1X2 wit"ngi3- it; lflfli tn 4 '51 r 125 J Anni ' t”. lCl-s. Salish (impetth ’E’j peyhfififlém xgwfi 8(ng it, 15‘ “layoff. “i 5. [ll] pts} {a} When recrystallizing a compound from a single boiling solvent, what two aspects of the procedure are important in order to obtain the best possible yield of the recrystallized compound? 1: 'th'SQ. isle. minith UdlrxL-H'F'fi a‘l salvo: potash. _ '3- -'r 1. 3 (pl L:- l ‘_-." .Tf'“ MA_ MILL fl} ‘1"- :3' L .__._~1 _ - .- _. ‘ x ' tailor-a. {Ni all; 1hr? a Hot to a . lb} Whit l5 it “5113”? important to boil) the solution duringarecrystallizaugn? H sclylshii‘i v. *3le who"? i-‘Tm-§!5;h\f- m.~tdo-.~B_si' ti pothole] Mus; We ll'u‘L (’7‘. r."—\l'l9‘."\f mistrth than: W.tt“,lW-Il?fi~—}. .. .-_ll 1 I5... .1 El" .l. _l£~__ Que. 1—*\_ I'll-1T “'91::‘1‘i CallI'llRuin-LEI“. .3 J ,l * {cl Compound A. has a solubility in water at ID!) “C of 12 gllflfl mL, and a solubility in water at 5 “C of {184 gtlflfl mL. Write an expression for the maximum percent yield that can be obtained from a recrystallization of compouudtt from boiling Water, after it is cooled to :i "C‘? rte-.71 first : 7;, :a we ‘ moo Otl'l a. {5 pts.) You have learned two different methods for filtration to separate a solid From a liquid: vacuum filtration through a Buckner tunnel. and gravityr filtration through a folded or fluted filter paper. {a} What factorls] determine which method is used for a given filtration? Uri“ f] F fifi. .| 9%.)“. w N [ha-— kfikkh j; {lth “kg [ Q. Lu slit") J .1».er taro-t mm, fikg m (FEW-high [? [we with J not? Ufa-4T} ‘l {in} What is the main advantage of using a fluted filter paper over a simplyr folded filter paper for gravity filtration? l- 'le-att. o; mafia 'S-atEazi atria [gt-r WIMfi'L i {‘99:er fiwfik‘lfifi T. [5 pts.) Eatarnine the ER spectrum below and label the most important ahsorhanoe peaks (indicated by arrows} by assigning thorn to specific vibrations (e. g. C20 sir; sp3C~Hstr: C-H bend; eta}. 1I. Is this compound aromatic".J N g. 1" What major l‘unco'onat group is present? rh\i\:ilr.& micrometers Transmillunrl: [rat-l 1.- UI "- -J G I: 5 IF E i . \_. . IIZI n I ' am and mi. tum Jamel .11th land :au Jim tam tout: IauJ lilLlJ Holt W uvcnunrbel [1: m' '} 3. {5 pts.) There are two majur functional gmups in the compound that gave the IR spectrum below. What are they? Wm I'I‘IF'F'I'IF'F'F'I'T III 1 I1I ! '1I I I 1 E 'F ‘I‘ ‘i' '3' El FFF¥TnvflufJI -"'~u-‘-—---——-- _.\I I . “I _ fi-u . 4 I 'd' I \_ull' n K -I-I' I.“le .u. 2 mm o-va I?“ M“ ad I . :III/Z' '- :Iul ENY‘ - I n- III-lug In“ “I'm”!!- 150 fir I (:0 «if- x4410 “:3 W: M . E“ *9 . \Hflfixamww%kkfi ED #11:: 0-44 ah” 1:.qkfiu1akag W1 a}: A“ I fit ~ W ~11” t-n-i‘ 1% H: err {BAH Afimkimfi 1%.“ MAX \a-“t N'H qr ml. QM fir {mics 3 [W mWST-E = II \ l3‘h.n,--‘1\ a): “b 1'I W0 CMJII {smug wjig :' I ’1 I I ‘ Ki”) flLII ~11 “Farr r!“ pct? -,-~,._ I L I! .1 _ - '1 - .‘h I if... - at”) 1“: Dim" ‘3‘“ '-“k§‘*’-\~:¢}‘.p.. .lxm m, m fit, QMJE‘Q . H fir J :M—x L# II '35-] film: 1' Lg .- tel; '1,.| g'fi-dfiwm-th £1.11!" ui‘f‘.-.‘ a. git-gr. 50 Fla-d. Lu: p¢.:.b.rH\--3 m T0TAL5C0RE=2x ii) = [my] ...
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This note was uploaded on 04/04/2008 for the course CHEM 309 taught by Professor Several during the Spring '08 term at Rutgers.

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PracticeExamI_2005 - DRGANIC CHEMISTRY LAB 3H9 NAME EXAM 1,...

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