Elimination background and questions_KEY

Elimination background and questions_KEY - Chapter 11...

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Unformatted text preview: Chapter 11 Elimination E2: fifimgwcmhm EQMKMEM my“ aka 9Q) «— al\ ‘ chH‘h aka M? m Rate = $6009“ \ kaj CKH?) My CR9}:- C VCR"), “\r Hiowmr’ c mwbud WW I H “5’ ’9 Q m Regioselectgxciit}? 0‘ c “‘13 VS a) ‘1”be ‘7 QC‘ > R F ‘ \NQOCVUW W5 \* qua mm «mm M’s‘qev : "-3? CH3”: C um—xg c.\~\3 WQ \o‘y «AIL ngéér A CH3 ¥Txx qwa V Zaitsev’s ule _ skiffimcw “3 WV V w“? ¥—\\¥QN& bxst WM Mbfi'mfld “Wm PYqu WM}?- ch E56. *2, \Q Dbfifl‘mxxmtfig “HA (rwmmfi ‘3 vemtsw'c’t -{‘ trowfg, c, snow \0 f 0* - - Excepuons to Zaltsev: *Conjugated- dienes and deiocalized electrons!!! .. (6‘3 C‘H‘g flchxxa : ax we’d: C, w (29 4893 Cmgvcm cm: CH ‘C‘V‘Q-‘i "f- ‘r\"c“‘3 . ' (“a We 1 (‘\’\3, \3 H3 C 1A9; C u. ec W), *3 T$‘~c Una 3%D‘CWME \ .W as flew—- u, A»; Wu: “haw / Qv—CH v (EH-“cgb- (ma) “k ” CK \ Com * Bulky Bases {rtbwc Vino \—\ ,1 C - c a?) Ckgq w. C Vt *‘ CW; —R€\\;C\“-b* /"'"\ (1le Q « {‘39: “C93 4% {23w (3 M CM C *‘3 " F as the leaving group. . .. C H C W a . - ~— 41 63, ~ 0 CCU \ocm'mx ”” ’3 q E1 D >“352530 “m” \8 CM Depends on: ° W $52 CC") {OYW°\W ’25”? W Emmfim >2o>p c \komiwaozgwwo é \Noicm (we: QM Mechanism: ‘3‘“? I c1343 C93”— ‘ "CH “ “2—9 “*9 CH ~C‘ 47 C“? 3 i -.’"'C%‘ J «w k)? _ CH3 “? O. o A ' \E _ Q? A. kwflvbmfit \ovacxk 8? (Wew 0 d LAdQ : ‘O‘I (44 4 v9?” WWW wawud cm: \ “(mm 1}- . . . b QYWOK . C-fiq at? Toul¥gqfig /*:\ l J/hcw CIA _, _ C“ O“ -\ - mam" \> (311 is, (flab—g $3”ng cw—m @C‘cgf‘lf a: ' g Y \H' ?> “C ~— 3 (WCB a 34% 11.4 Competition Between E2 and E1 \L M Ms \xv 3:: 4% CM, P ' " ‘ ' ‘ \buo (imam hwy“ cam. ‘ . f. _ i 1.5 Siérédciiefiiistry of Elimination Rxn EB?) Elimination "Back em attack em Axe basket . \ ~ ;. "(L‘ch \A afield? r1313“ a—fi Ca? :2; CU ’"OHQFC H3 NR3 9” \ ,0 '5 C5 . E > CH3 ' 2? pt YHa ‘ ' ' “\Wv Regioselective: Mb“, 9‘ \ m ngMth C Stereoselective: m W @Q sumac . a If 2 H are attached to the B Carbon will get a mixture of E Gk 7/ Major product will be K9, WNW?) W3 a If 1 H is attached to the B Carbon will get Wmdepmds on WW0 OMWWR Yflouer" H E1: 0+ 4:391 215 (\0\0mcu\ \OUW\ (5%)“ IW‘. ""9 C‘W’C “\CLESDV ‘P" Ufl-MJv EASE-xx D“ Ovpbéfln @6424) . 11.6 Cyclic Compounds E2 Anti Elimination: XandH mustbe ' S M1333 §§10V\ OWEN 6 Membered rings: Xandeustbe Qi {09. R /\ /\ X Rate‘ tmv W x. «x» \\ “m w» MM bwt weed 8mm cmw M LL/Jgt‘ ‘* a 3" L> WW {:Uw . H “03“ (Mm YQWW -§\’6V\,N J9 C \pMdm Wfi \xcxx—Ekaua W\ MM?» gamma- E1 ’- ’“ Mew CED 9mm "* WCMQMW ““ 1399‘s . Rafimsva “ambiant (.— dzmsfik Maw-aha Eh OULWKQ‘ rte Lumen "va Gr ‘ t 11.7 Kinetic Isotope Effect W5 / “3 cu; . . . 2 L . - Deuterium Kinetic Isotope Effect A _..,. {m C \4 MW \Ub Ym cmfiéd cvb 11.8 Competition Between Substitution and Elimination W WM - Bulky Alkyl halide 01' Bulky Nuc/Base E1 vs 8N1 N) \D 20/30 22> ‘%D><\r\. 11.9 Substitution And Elimination Reaction in Synthesis WilliamsonEther synthesis K‘fisv * 9‘0" "*9 \Q”0"‘\Q —> fifimfir—awmouxcmm :20me {E33 8N2 Rxn: Md 01va km amt—oi LVN-X tawnm» WM E 1 (2M:ka 13 Cwaow ;\. ('hg‘CbefiW a...» C‘A—bbu— cw,ch qua C1609 C“%C“1’E>V *O’gcfv “*3 CHECH'; o V g ~ CV3, /3'—"\.w ‘1\ \LI/ “7’0 M/ 4 \V/"C‘Aar‘y & xifo“ 3:sz “ma - 6L (“313A cawmlggurwg W; (Ham Qua—cum: cumtvb cmng Ct at ‘9 flgcv-wcx‘vwg 12.3.» (“ECQWCHChg ‘3’“ > (HgCfiCCH‘g awn/we C‘ 2‘ mow “ (\mrw hunt I 1.11 Intermoiecuiar vs Intramolecular Reaction “>4 ‘ 5H9 WmmvwkmMO/j ...
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This note was uploaded on 12/05/2011 for the course C 341 taught by Professor Skagg during the Spring '11 term at Indiana.

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Elimination background and questions_KEY - Chapter 11...

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