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Review%205 - Eew'ew Sessx‘on 5 HDTE Title Reac-h‘ons‘...

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Unformatted text preview: Eew'ew Sessx‘on 5 HDTE Title 3/6/2009 Reac-h‘ons‘. Gr | gnaw-d 3N2 5N1 Arrow—Euskfnj .. n: .. Hgte H—CI -—-> Hg-H + C\ arrow a‘waas 3°€3 Prom o‘cch-oh r-Scln (tame air or seamed-{MES doubt bOndS 4o elec-I-ron—POO" S‘HeS (84') NM 2e“ \2' Gri non-d ‘3‘ M s- + 9 @ sows R- CH1“X J‘- 12-6142:ij <<——T- R'CHz MSX) VOV T T g a nudeoykih‘c COA’bOn! +h|‘$ resonance WWI? Show: 9 on carbon nucleopkHeS: Lewis bqsu‘c, etec+ron~rick, wan+ +0 S‘mw'e e‘ ehc—h—oflnfles: Lewfs acidic, electron~Poo'-, qu+ e" '3- .. - 3* :o;6 0H \/\Hjl“" use/R '4 -——‘> Hsc’ CV” 99 Formmuekjde 9 H (5 H + H09 MgBr MgBr new c—c band! W \suhk eroduc‘l's a? rm w/ CH3O-H,_— M33? kebne 5" Co <° “Hekjie 0 SO do TfiL“ M31 {’9‘ Jr“ HAW: %€H2‘M33' CHER: c3234; 0'35“: 6836“; Egg: :2”, i L ¢ $3 T ‘ 9 O 99 H“ H 14%“ "‘ E2 ‘ M fi" A 0:23 La* J, '4" V" LH” V” on OH 0“ on on H H H ”t" CH1CH3 jj CH, CH3 ‘0 q\co\no\ 2° «‘00 he! 3' alco‘Mfl Ano+her use OF Grignardfl D 2533’? I e @3543 Br- CH3CHz—M33" CH3CHz "' 0D cure-pun! 6rignw‘ds win reqc+ wi'l'ln any; acidic H's (b/c +he are eted-ron- Poor, eccl-roPha'n‘c.) o . H’0 ‘H A0? W» m a mtg-8° 6m: . in Ic so V n K/ auda‘c Pro-Pan u,“ gs gnu wa'fi ‘an rm above SuVosH- Hut-Hon Ream—Hens 5N7. Subs+€+u+€on nucmo‘mih‘c 2=bimolchAcLP k t0. no" ff g?‘ z mowcuxes favoured in kg) fie? (rah-«defiermin‘nfi G A A SW73 Nu: l A y NH- .. _ C fll-nl LG ’ a ’9 C Q0; '1 A": 3 ’I Nu B C C I 3/ 11. arr-onsfifi'oV‘ s‘I-cd-c mversio n 09 confismmfie q ,EA/RT E k: e r‘a+e= kENuf‘Dz-LGT‘ % V'Kn Qrosdss second—enact egn (1+1=2,) owns) one my! C\o~$s Exercise: How +0 ge+ re—ren-Hon 0F amfisuraHm—douue invention} G e a * 5' @e ‘4 No.1 n H NaoH \ ’—, I - C. M ”I": ‘OH \‘lCH3 “36 l CHLCH3 CHzCH3 I- act: as a t‘ ' \cav' nucleogkhe u'n you: .9.“ mpg kn: -|-o be good o.+ bo'H-s Hne firfl' SR? (gamma 8R9 Anal-her 5N2. '. G e ) {aver-NJ s+ereocen+er ,L. Kou ” f ————-> OH I" (jar 1 .1. mo\ccu.|e fmvor-fl-anfi- fn he: 5R9 SN SP" ‘f K 1‘ me A ,. - m 4. l l C,nc\/‘l}é ______,, >l C. :Lq ———-) + Cl, Ill ’1’ / \"c a l' m B 8 SM. 3 / MOS'I'hj race-n“: INTERMEDIATE (M+ T3,} E 1. I ra+e= kER”LC11 SM" “73+ oracr rcac-h'On «0+2 +ha+ Nu does “9+ o-pFeaf P .—_—_——A rxn fro 5N5: +/\ 'CH30H’ +/\ "' HBr A OCH} CH3OH CH3/ @H :ére 0K, EL; (\3119 key-u kooky-13 ‘ o c" 1 cu}! CH3CHLOH X ’g 1/ HO CHLCH3 “ ”(\‘p @/ Hé (Hazel-)3 (5'9 \r‘?\,H k4 “2.0 ’7 ko‘cnzcrg R now HLO f5 0. good LG; A camearison 5N2. Sui s+¢r¢ookem€ 8N3 {aver-Fed ?\cu~¢r garbecaL-Hon (nflrmfifqfl ——) mcemi c TS encrg-g dfaa'n'“ E 5 c5-B 9” SM P P ("Kn Pros ““1 fro: one SK? aha-Io SN? ra-K. is uMH-cd 53 ae-Ha'nj ran-m \‘5 “mini 5:, ‘5 Ohms ”mused PQP"\3 Fumes-Hon 09 around a can‘H-a.‘ C. carbocA'h'Ofi t°>z°§<3° 3°>7_-% 3" down“? 90 \° daeSn'i-go s+o.h-‘\'n-€ carboca-HOn b3 kq9ercon3u3arh'0n Nuc a f as linear, 8° 3““ elect-vans +9 shore (usu. [one Pair 6; 2'3 :NECeJ 05+.“ have “a “five char-30. (be-Her {F +hej do) CHB q.“ 3 e 3 H o bad Mu smauer {s be-H-cr ’c CH3 More eotafizabu is be++¢r (1" > B" 7 Cl" 7 F7“) suz $.11 needs A venj 9°06 Nu “Su- neu+rcd usu. (-3 oF+en Hue Solven+ neva'oA is ?oS$i\>\e (c4113) (solvoljsrq K Pushes 2 wt'h'bvéuifi 5., Le cthHM' HS? 2.56 vecw,1:9 > N? > aAoe > Hoe> 09 o I; > m9 7 NH3 > Ads > HLO Leavt' n3 GPOMES good leaving groups 8+abs‘\{7_e neaafive charge. we“ good leowa‘ng grouPS are consusqd-c Bases 69 Won-‘3 acid-3 F“ %’0“ f‘o Hi. -3 g“ g: p A D / <L TSOQ excellen-L LC, Kg $5.? H10 23 H09 + H9 K “9"- QS' 3094. LC? LG: (Cofl'h‘hued) 3N7- 5N1 __'— good Lg, PreFer-ei needs an 21"ka good L-‘a- (bu-e “0+ a: s-I-ringG'V" as sgnfi Tao“ - M80“ > Br '7 c" > HLO 1‘ 5 leaves he“ SNZ. SM Sokven‘l- Pohm, EPr-o-h'c Pawn-I Profit. soIVemA- O NABr _> §a®+ 3.9 s+abifize LG. 4, CG"> :_ O u ' 5* ~-. H’°' 40n'4- wan+ schist-Hen *0 | H no”. .' \ O'- I ‘ 9 H O L:V\ée( nuc‘eOPHHe H/’" ""0 ‘76- \ “0H '. :4 \ /P\N/ \ ,U\ u o 9 I: \N \ [r H ’s\ A 08? 3006 ‘0" H / \ e-Io folvohgs-‘s H. DMF DMSD QC '9 . HMPA AfiM‘ (J's I H'O'H’ H-D‘Cflga-l; N'. Me-CS-M CH3N01 J \/ mebnifi-I‘it n i-I-v- cane-khan: Guess +ke Ed'i'? gyr- 4- \r-ge. Lie -—-—) \\o/\ 3N7. u :“v r- i’ o: c :gng‘flkiqmi,’ :3 8'5 l° carbon good LG .5. 'I I I 3" carbon Suver F \/\ 4— +ern'bke La! Class Exercc's‘g : 4. \ he-l- «‘1' A chirad C3 J7“ ” A?“ 5'41 IOE+ E0- race-mic mix-rum 500A nqcmop hhe E+on —-—9 So- So 0 mm eoPkfle. eyccll evfi LG; 0 G. \ N363!“ ———3 no I'Xfl. Is he FuUOwina read-ion Sud. or 8.47.? w”? on bu‘nderc-l For 5,41 appronok'. ' l- W}? CH3 ‘00” H kl 'nnverJ‘I'On oc- wag-'3 I'vn fd'l‘, buff considor a.“ compo-meat a? reach'on H10 T CH3 (LG, Nu, substra'ie, soweni...) 3° carbon no+ venj good Nu (:sz 3004. LG u, (1; he gr ‘) S N 1 ‘ e ...
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