MT2_S99 - _37_1 mam-Ham 3&1 Joeélyn Grunwall 1F I[15...

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Unformatted text preview: '_37_1_ mam-Ham 3&1 Joeélyn Grunwall 1F}? I. [15 Points} Name or draw. as appropriate, the following moiecules accordan to the \UPAC mies. Indicate steraccnemistry where necessary (cis. trans, R. S. or mean). l menu“) __ '— CH3 0 iILIH- ;_ '1 Aurt'lil-JL -'. mume "<10 ' B. m 1-rfrluh-V'H-“l 7‘ CH3 _/' CH3 . l-mt'i'v- [a I Hint: R0 is alkoxy. .77 7 - —— .. — b. (S) -2-(Methyiethyl)~1-penmol .H3 ; \mrwi 'ir-‘rlrjfiro‘i LI— 5 H H ; r—irvH 12m; { CZ" H OH 2’. $2 ljl.t1'..flr‘vf’61fé’i ‘ CH3 ._ ' __ _ . IH. [40 Points} Explain the fonowmg observations by a detailed mechanism (Le. write a scheme with structures use arrcwipushing to iliustrate the flow of electrons. do not add any reagents!) a. CIigOI—I ——* achl raJ product Mechanism: ‘ “a. 9.- In 0 H _ _ L__p. (Hg IV. [30 F'biflts] For each pair of reactions shown below mark the box on the right With an "X" indicating which will go faster and circle the mechanism by which it proceeds leg. 8N2, 8N1. E2 E‘) In one complete, grammatically correct sentence, provide a brief explanation in each case in the bottom hex provided (i.e., explain why so-andiso is a better nucleophile. ieaving group, solvent, etc}. No creair will be given for the right answer with an incorrect reason a Mgr Nam‘CH3(m /\/‘\/CN ' /\)VBI Nacm—‘C H'I'OH mCN / -. /'“\I (64/5 fi—m \shii 7 E2 _ E._ ia." ->|. Rhianrhirg ir=lM hniuaikant Il"‘-‘. 41H; "H. il'. lgi Inflifl ".'|§ Em C .v--—) I _ i = ' > In; 'wmicam |-'r i‘-.nl(uiililui gmksli 1min NaBr L 0H b. 6 —" | V EOH B HBr i' 3,42 an E; . E1 c CH3CH11 CHJCHgl fl.le CH3CH2NH; l3 EL CH3CH20H I: E; E. 'NU? I\ a brflfr n.)“f:.-Phll€ ll‘.‘E'|UWIC_ (I '15 hm; huh: Hum '[lH l. h nut ml oh palm.le [3*k'filf) {a [25 Points] Consider the fouowing transfomation: NI-Ia /\( __.. F H3N*F‘ Provide two ways with which you could dlSIinguiSh between an 3.2 and an em mechanism. 151 Method -' _ . . . r I! - [specify] '.tFI-’If4.hi'h']:¢m| .HIHYI-‘hsr‘i \[|?'\(u\‘r=‘|ri"-}J Expected result for 8N2 1 II we.rIa:n.v.I<\'1Upl'nrmly 121‘“- HHJN’J rpm “NIH n'Juumlmnmnaf ”h\rIJ1=r'-i“ 'Iwwmpllr H‘Tvl\,11rI?rHllIL'i: wuwd film W I. , NEH“qu mhu. l, WU:an «he, Expected result for an . 5h”! Ft‘athr‘q {‘(ul'une rm Hm"; ll mmiuli “I! gm orlmrpifilj mind [flflhflufinr’ “10 Pub”! “Had [It £||frtrm1r mtth Jami l‘nml .Ynunf “Imp”: (lrhll “Q Hrl-r-mfrlmk', 2ndMElh0di ql'udnn .all'J' “My” [run-“\lnlhnonl .I, IIJ Irrurn «J (spemfy) . _ .. Expected result for 8N2 : x“! '-.... . __:m-l.,‘1{-. w” h.“ Mum firpwr'li Wm -..-.f,|_.1,.._alpthdig-LIJH-Ikl[1'1th '-Iv"-'i'l '\ Ehll‘l- ||r -'-'u I\«‘,|'.H--:. 1. I: Ill” N Lil \, I ll Expected resun for Su‘l ' . . . . .I .\ . , J |\_ \ I ( I I. I | .l- "w ' ' v I t- W " ‘H "‘ tMu'. 4‘- hr 1 '* }"-"1&'r." r. II ' +f’ a 1 ' H; I (F ' I camcm A — a x x E] H3C F if b CH3CCH3 \ D an: an E2 @ [_ ‘ [Ulllngliubrflf' lf’é""'fl T“ f" i humus H .s laujt'l' WI“ 'I‘M'i' “W |,uhu‘.d§'1{l'nclu’jfl CH_ _ CH ‘ c2135 ‘CH30H 3 H——c1 4-—- CH3S H H——H H "H CH3 CH] (":H ‘H 3 CHJS'.CH3OH j 3 — H—'—Cl —' CH3§ H _. H3C"' _H HJC+ H CH1 CH3 8N1 E; E‘ N“, ' HHMJLL J I r I T I I 1 1- \ \ [30 F'tgnnts]l Provide a viabte synthetic route from starting material to product. Use the back of the {3399(5) for retrosynthetic. anatyses Write the answer in the forward direchon indicatan all necessary reagents. Do not show mechanisms (arrows) CH: tasthe only ' ""4 organ]: starting material) [mixture ot‘diastercomers) _ ‘(_' ‘ \ _ r t “S \ t / r (“5 \ ________ "a. 6) OH ""SCH; Optically pure optically pure ‘\ \ / L «s' .' 3’ 31"» J \ t L YIN? _.__ I ll ’11 b. Dlaw rough potential energy diagrams for both processes. $.42 ‘\ T E I. w.- _ SM ‘1‘ J , x, P SM = starting materials. P = product 5.41 ' , _ \ E] . +2 SM \r ' P “1155 Pm" MEL]. uzmus f THEY PLAT A LCT II 5‘ 9130:: w I'r' | 2 DON'T xw_ "'I'Il'hwlc-W..-“ [60 Points] Add the Missing starting materials, reagents. or praducts {aqueous work up ‘5 assumed where necessary). Don’t forget sfiereochemlstry‘ Do not write a mechanism! NaBHd __.. “ix” \J I l _ 1. Mg I. 2‘ H2C=O fir /\f\ ‘ 0H CsHuBr . .x | \\ ‘ U I Nqfiu _ _x _ MBF M _ a H _ 1 ‘0 I IL I ff i2 ——-——‘i' MCLCPE H 0 1. CH3EON3_ 2. NaOH,H—_:O __.—- fib 117% L1 racemic Suggest an explanauon for me excess trans product Explanation LPIhllhI1i‘fidl'lTi-l \‘IH'. r'GIhEImIr pl. AIWIIH hl‘inru. .. 95,“. Ll._,;..,..t \,l \ al\|lt"\ | H‘f‘!‘ |1 IFH 1m buikt} 3'5. ITgI1P‘h..r-r~‘ ...
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This note was uploaded on 03/09/2010 for the course PHYSICS 7A taught by Professor Lanzara during the Fall '08 term at Berkeley.

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MT2_S99 - _37_1 mam-Ham 3&1 Joeélyn Grunwall 1F I[15...

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