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Lecture 12 - Minor plane Enantiomers of chiral diastereomer...

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Unformatted text preview: Minor plane Enantiomers of chiral diastereomer tmns-lJ-lemmocyclobutane 18.25 same as 15.2)? Meso diastemomer cis-lg-mbmmocyclobutane L i “A I C and “I l‘ . A ‘ tc flc’ 6"” H . f . L ‘13 k \ 4 ‘ L 3'“! AL‘ W’ H 7 3 ‘ A. . C A A lntcmal mirror plane {launch ax L—l / wk [woqu wk. «(fu— W241 470’ \ ' 12¢ ’ J A L A A A 1 _ I, " f ’r / 8 In C~ 4.. _. -- v I l l /‘ A , u . "| 0‘ . 0 So V i Mmflm / O M V; r Ir'V ‘ t WC— MA 4 i Curaht- 0 m k ' 4 . A A It "A‘ A A A g“ AA ' A- I . I" ACAW O K n WM 514*. “(A I AAA. ‘5“ ‘ A a ' . . t ‘HI:“---'V'J"l I '7' ' 'l 7 FY i v ‘ n y . . , ' - r V. - . \ \ '7 '7']! V I """ ‘I I r7" ' ' ‘5 l" bwwk J 6’3 \* / l“ c——c.«“ ‘ 05'“ IL 1 \ TL; mW‘q/C 0'5. Lt; 4 nu , ". . I Mama 0 c. " OM ’ ’ a: u. r , j) r ’ as am ' rm 5 “,3.“ M NV ’ SM . Wad. ram ' ~ Hm I» ' W5) - 4M 'T’S . 4..va r‘ ww- 3" 2‘ . _ Raul «Lou! 7'30" “.m‘ «K * _ W 1!“, .2 chug at m 44..»th "m '2. 0'“ ’ m *4 " — V W m menu 3" L 4" \ “‘gl‘ “ “C; 4 an "" i \ a": l ‘ ' S K 9591 7C. ‘ W: M cure. Aixsfihoma - ‘! St 1A : ""7 ‘ - l soLufioN . ((Acémic Momma c. Marco.“ a WWW: om A M15454!“ ‘ m .. z c. w W van. _’ rmarwh 0 cmer: M o .AS’QV'CO mu": am Lo up.“ ' ' ' Y 0H COOH TH} + H H — “0H CH3CHC =CH HOOC H Racemic [R.S)—3-butyn—2—amine (+)—Tartaric acid leo, several days 0 O \\C O- H g H \\ o— H INTI H OH _ 3 , OH — 3 . “H )s + HH 2% “0H H3C 3% “0H H3C Site HOOC H Hooc H Dextrorotatory [+)-tartrate salt of R-amine Levorotatory (+l-tartrate salt of S-amine {12125: = +24.4 MEET = -24-1 Crystallizes from solution Stays in solution l K2C03, H20 1 K2C03. H20 HIN l-l H NH; ch %\z~$ H3C 5 a“: 47% 51% (R)-(+)-3-Butyn-2-amine {S)-[——)-3-Butyn-2-amine [a]? = +53,2{:1) [slalomC = —52.7{J_r1) b.p. 82°—84°C b.p. 82°—84°C (Z) old/{ml ckmmar03~raghg L :yongo Ofowwte ( Mary; Univ) Eluling . _ F i r \_ ,I — solvent I \ ' \-. -’ x We enantiomers Md—fl—M “CM begining to separate J “”9? ‘ IL” a fluvial mural Mg} flu. Silica. I an. dumn W‘ Red enantiornereiuted W before green one. Time / q ' V V ," I’3QVII "l' Schematized Enentiomer Recognition in the Receptor Site of an Enzyme One enanliomer clocks The other enantiomer does not fit (as well) into the receptor site. in an enzyme receptor “pocket." Poor fit O {and-“£5 0| Mo Fad-«4‘ Miranda“; QM, ‘ 1- 1 3"!“10’0 —' 2.‘ MM! WM ‘ “ em I“. (a) ”(3) Nawvu Lonau?o|m~ak a] C Axum: M07»! and Mid Suhfihufs Law; 6"- Sam pn'oflry ( dpkchh'cJ cal“) QM”: 9| sflrwcfams‘d’ry C L or 5') g” ( (5, 1&3—1,z—uLvm chpmcw (Lwr flrf (‘klzsj ( 34mg! Mcso‘. H‘l Sic A L PROPEIL‘TTE'S 7am. twig“); palm: lam $4. “95‘“ TC Vevfi/ {.(uXIoMSAWe _ H ‘C, / 94,-: 1.0 1047‘ :lfN H dimomdtuu I . Twat ’ L‘OMMJ ’ 'nuf MaloJKaus r— J' Q41, 3 O1 ...
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