Review%206

Review%206 - RQWGW Session £2 EHnm‘ncrHOh reqc‘HofiS...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: RQWGW Session £2 EHnm‘ncrHOh reqc‘HofiS (El-l- El) Rear-ranger“ ants E1"- s+ar+8 ovu- 3u3+ u‘ke SNfL, buck Q,\\‘Mir\a."¢8 ins-Feat; o-F o~ nu cleo phu‘le adding HZ '0' H H _ -. a I .H £3353 C "'—>,u\a are 3’ ' a: long as +here is q mezshborinoj c w/ an H +0 remove, E1 wan compe+e :0] Sun. ' I'F +herc is a choice of: w'm'cln H +0 remove, more subfl'i-Ni-cd A°UU°R b°"ds “’9 ’eFe"ed b/C +9163 are more s-I-oJo\e, (Saj-Q-zevls Rune) H418” W ~52?" New a a w MASOR minor- ‘-\ SubS‘H'hken'l‘S‘ 2 SHbS-H‘tuenfi's E1: cancer—Had eliminq+€onz bond momma and breaking happen o.+ +Ine same ‘Hme. 9" +0 H E 4, ER)9 Nate 4 ——"’ + E+OH + 3.9 Br B+0H ‘ “‘35 °t S'H'On‘j ‘OQSQ “'° “Push oFF’I leav'usj car-cup - b/c H's Cancer‘Fed, geome-I-VLJ is im?or+an+ Cfl3CHzria> (La HJCCH’k :CH;CH'3 CHICHj cute“) <1“ ' ‘ ‘chuzcuz a 4"1'":\ = ‘3‘)" CH3 M: Me. Hac CH3 LG CchH1 CH3 g i i —-4 CHBCHL CH3 CHSCHL CH3 CH3CR;’—@:‘cr'3 H thor g: f H' LC» are an‘h'Pefip\a.na.r CH3 E+oe fl! 6“; Ex 1 -. oflzcm¢Wf33 H q “H he H c 1"} 6 -—v >=( H Br “5 cmcuzLEr “bah. CH3 c-oi-aue‘ single bond +0 ge-l- H 1 LG. an-h'PeriPlanar EYZ‘ H TSO C .6 2 m Ts° .- EI'OI-l ' Hac H l>'fl A New ma n It as? proseah‘on 0F 8.14, w/ 0T5 ecvaad'orl'a‘ Shows +ho.+ +here's no an-h‘periPmnm- 1-1 T301 H ca: ¢,-cH3 . —> 3% we CH3 H" CH5 H: 9, 05+ new Qn"; PO'IIPmmur IF +here are cko3ce$ woken-e +1: eHMinQ-l-C'. - Firs+l more S'Vable doUJMe bonds- are pavoreé +rans is Favored Over ofs /:/ S-reI ,2} "Cw-Won Hams of: if fix: base. used (5 huge (8333, .'+ wm fill-9 +he. Fro-hon +|AQ+ is eqsier 4-D access —-> iess subsfifl-ficd double band 3 885'. hBuoe LDA 09 Q be CH3 \l “3 CH [‘39 Ex. I-I E+daNp —‘ A. C a -——9 we PH 2,, / E 9:: %/ U vet-3 m€nor - he \M‘ndcred For 833 +0 ge+ 2° H's Mechankm For ds and ‘h'uns produc+ Formed-ion: 81"? H OH H >M‘ a Q *1“th Produc-L H t H CH3 81"” H . '1 “‘5 ‘\IH ‘4 H ‘ " cu's Produc-i- CI CH3 How do we knOw uk§¢h reac—Hon +0 expec—r? Good LG? no/ \ gas no rgn 6°96 base/nucleophhe/ne“Haze- . good Nu (142:3: Strong base (1'. RS”: 3"3 I ' Lace, 0k) Carbon Cefl'R-r con-ho“ cennr carbon can-Let“ w/ v/ \v \3° v/ I” \r 1 El E2 no rxn SN l SN?- EZ Path Sui 5°\V"‘+ Snl EZI‘FBBB b“""°"‘° 1 (av- who ( 3 “Pcfll PM.C Sal Sni Comean'SOn E Sn La, memes Rn“- Lg leaves {RV-84- L.qu cavbocwh‘on have carboca'h'on :1. 3°7z°7l° 3°72°>(° Pckar‘ on‘HC solven+ bes-l- Polar Prod-{c Solven-i beg-l- Fowoved b3 he M— Lb\ mcemizes s+er¢oceq+er ‘2 LG pushed 09F LI; Push“: er can be l°,1‘l of 3° l° 7 2° 5 3° Polar «Proh'c CS beS‘F Potar aPV'O‘l-I‘c. u": bes+ (bu'\' of—Rn use a. s‘otverd- W'f Correspnds 10 base: 809,“? :n 5+0“) ‘RVCPSI°" OF WTCO¢CGKF backsfde wH-acu FfiVO'N bg head” gmau, good numeopkhe H' 4. LG MuSi‘ be arvH Peri‘DlanM" 3855 are 59.34— Refifransemen+s when 0. carbocxfion can be happ‘ef cuewkere and MOV“ usvtomg 1°--> 3°, lou+ 3°——» 3° {3 also Possible, yAGQ W“ hjén’ae stFi- H? “hgdn‘de” H e H cuk‘,‘ skiF+ -CH3’-CHICH3 _9 fl Phen\J\ SWFi’ @ Ear. wk-.:h a? We Fouowims 0:1“ kave carbocah’on regézrcxngemenf’. j: 2.1; %(t' nuke-e For e a, move __, A /\\ oTs ma ®2° [’24. n,“ H Ag 3N1 El _—b w oer * fi/A/r H % ““h N «finer Prodmi- b/ Icar Igogarh'on rearr. (8 {hm-er +ham rhcn' E+OH ) YFOLC'HCQ Prob\EM8 E) &/+)\/ (wfinofl © 1 7. °"‘ lose I, gain on ——> Subsfih‘h'on ——3 JY AF no+ 0n same carbon .—) (Carr. 1' “to . “WA. OR /®\( reArr. @fl.‘ '- 03 H . eL‘ {rm-Hon OH H“ ‘T: 5.1. u, ' “N Am I no area-i- Nu Caz? H10 need a flood Lq -—-—) wanna): OH 1"" H ‘9' H 19" rt: qf \ —) H 1 CH3 .-——>H CM 4— /=\ + H 3 M”... Irlsc CH3 /\“ 693 "d... at minor + Hao+ (= H"; ago) 60 '2 2. More C in rel-P +ham S.M. /\‘/I ——I—9 Ah Gr§annrd rxn can do +ha+§ CH3 CH3 0ver +he w; M9 l. M3 A°’\ o 3-9 AOA CJL ' 0: OH 0 CH3 cm HLO ca} 3 H“, H20 l Ht “2,0 .m “‘8‘ q “‘3le H123 H e A Z A (e7. / 1v 3 /Y\ {—— /§/\ é‘" 0H3 cH3 CH3 Liv“: emboeafion could «I30 rearrange 10 make 3' carbocwh‘on' +9“; wovdd awe we Same H<\ Q\\'M{V\Qh‘ov\) Produo‘i' /\f\ 4’ / ‘fa ‘ 16H,- 3 . O-Hner ConceP-rs +hod' we Bowen“? koud Hme. +0 +°dk doom-‘- in review: MESO; Mega compounds kave SRreocAni-crzs‘, burl" are no-\- chirGJ 44,“: (3 because +he3 have {nRth‘ mirror- Pman C‘ : c‘ K ," C\ : C\ 5 S | R l _ ' mirror image 0‘ 8 M830 Inf-Ornad : con-“Pound I'S 1"h9 Same flawgr mo\ecu\e 9 Ho \86. 6° on 0H HO 0H m OH “o OH I '- . 5 I '~ '9: Is' 5 P's I l l U anmal mirror P‘ame'. (+5 Mose e “om-H omers Se ara‘Hn enanh'omef's (D d-‘afiereOMeric Crgs+allizorfion ® cki rod chrowwtogmpkg ® Cflj Sm“ Kza‘h‘on [, ream-l- \JOuf racemic acid wi+h a chiradlg Pure base ( " " " base “ “ “ " acid} 1. cr5s+atize +he resul-h‘ng dioS-l-ereomer: (add—base cemple$)J‘ 3. safe.er eras-Pal: R'Dm ligul'd '4. Eeaci- \Jour now-Pure comyound w/ qu'd (+0 regenera-le {+3 ll “ I‘ n n “ base- ) Ex: CH3 n “‘3 09 CH3 0 . + OH \Hh_3* a r 3*H H ‘ \I o 0 ° H39 CH3 v A -_ * = e * -I- (O‘Ht‘ B o 3 H __,H (j lo 13‘ © 0‘ W4 . Cklrafl " memkc acid Pure huge gbgsg‘$?;%figrs keg-l" +he now- _> crjmune P‘tfh a??? W' QC sePar‘d-els resenem-lc en‘s. Commufld ® Chrom q-I-o 3r apkj Ck;l'O-I comPOUfid (I‘mrnobffized on a cotumn} Fornns Flee-Hus fn+erac+ions wH-h gour duh-cl mo\ecuIe. One enonfiomec- react-s be-M-er-J s: f-\- chicks 1-9 +hc cotvmn be-H-er and cud-es \odu: Ex+ra Pracfice Problems @145 +hem Rnfi')’ answe'J be‘°‘°\ CH3 CH3 (5) 7 ———) CH3 8H3 CH3 Bf '7 . . © ' wuu x3 ++fi3 reaches fiasier fhan +ho one —') E I in ‘ ‘a'. CH3 5“; ? SCH3 N —'—-) AnSwer51<Howe \Joq +m'ecl +he Frauen: Fin-3+?) 32% H m, CHJ _ _ Cs) “3C __, L out! one H I: anhpen‘?lanafl go 3.. CH3 ‘f , H +he Produci- shewn Ls +he Only 6 If"; one 1:088‘ble “'9 aha Si'ron base Wmesa: 602+, 60H, O-bBu, e+;. Br HC ' © —+ ’ + WW "c::;‘“‘”‘“’“*°‘ ff“ LQ>A L “3 +wo H's om‘Hperiplamar —- +o gei- +he less Subsfi-fwlcd Paine-+3 use a 533 fine 90+.Bu. Tvu‘s ream-Hon is Fos+or +ham +he one €n© beccuuse i—he rx‘ns preFerJ‘ +he chair conformed-ion +ha+ is reach've. 1+ down”!- kave +o Flip +0 0. higher-energy chau‘r +0 rem-AJ m 1"? does in - ® 1) BrL’hv SCHS n “ted a \ecnn'ns arou? N , --> use monokdogenfion (Br (“05+ SQICC‘HVC) 2.) Nach 7.) subs'h'h-I-e +he kqfide DMF —* can use (IV-1389 -' H": o. green-Pk“; («\so use a ?o\qr’ aF-ufic solven'l‘ For 8.42) Mae 3"- CBI— N ——"kv /l\/ DH: /l\/ bO‘Hn bo+h ennui-{omens enanfi ome's ...
View Full Document

Page1 / 6

Review%206 - RQWGW Session £2 EHnm‘ncrHOh reqc‘HofiS...

This preview shows document pages 1 - 6. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online