Chapter 18 Final Packet!

Chapter 18 Final Packet! - Chapter 18 Packet: Final CHEM...

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Unformatted text preview: Chapter 18 Packet: Final CHEM 1898 Packed (Hopefully...) Sections to know from Chapter 18-: e The acidity of an iii-hydrogen - _ 18.1 e Keto-Enoi Tautomers 18.2 o Enolization 18.3 o How Euois and Enoiate Ions React 18.4 e Halogeoation of the o-Carhon of Aldehydes and Ketones 18.5 0 Halogenation of the dwCarbon of Carboxylic Acids: HVZ 18.6 9 Using LDA to Form an Enoiate Ion ‘ 18.8 9. Alkylation of the u—Carbon of Carbonyl Compounds 18.9 9 Aikyiation and Acylation of the tit-Carbon using an Enaminc 18.10 e Alkylation of the B-Carbon: The Michael Reation 18.11 0 An Aldo! Addition Forms [iv-Hydroxyaldehydes or B—Hydroxyketones 18.12 9 Dehydration of Aldo! Addition l’roduets Form £1,13- Unsaturated Aidehydes and Ketones 18.13 6 The Mixed Aldol Addition 18.14 6 A. Claisen Condensation Forms a B~keto Ester 18.15 9 The Mixed Ciaisen Condensation 18.16 9 Intramolecuiar Condensation and Addition Reactions 18.17 6 3~0xoearhoxylie Aeids Can be Deearboxyiated 18.18 9 The Malooic Ester Synthesis ‘ ' I ' 18.19 O The Acetoacetic Ester Synthesis _ 18.20 And new for mechanisms; i? Keto-Eiioi Tautomerization/Enolization 18.3 o In acid AND base f’ Haiogenation of the tit-Carbon 18.5 0 Acid Catalyzed—only add one haiogen 0 Base Cataiyzed—haiogenate ALL owhydrogens o The Haioform Reation f Haiogenation of the d—Carbon of Carboxylie Acids: HVZ 18.6 1:? Formation of LDA ‘ 18.8 M Use of LEA: Aikyiation of the eye-Carbon of Carbonyl 18.9 o Thermodynamic (stable) vs. Kinetic (formed faster) 0 LDA = Kinetic Base, *OH or ~01! m Thermo Base 0 LDA removes from less hindered = irreversible o Thermo base 2 reversible 7 y” Alkyiation and Aeyiation of the o—Carbon using Enamine 18.10 M The Michaei Reatitm ‘ o Stork enamine reaction f Aldo} Aédition o In acid AND base (acid mech NOT in book) i Aldo! Condensation o In acid AND base (mechs NOT in book) 0 Mixed Aldo} Addition y” Claisen Condensation 59’ Mixed Claiseu f Intramoiecular Condensation o €laisen (Dieckmann) AND Aldo! _ o The Robinson A'nnulation f 3-0xocarboxylic acid decarboxylafion o In basic AND acidic canditions M” Malonic Ester Synthesis y” Acetoacetic Ester Synthesis 18.1} 18.12 18.13 18.14 18.15 18.16 18.17 18.18 18.19 18.20 Mechanisms and Practice fmm Claisen Condensation 0n: ' . but: - - ’1. Claism CondmsthI 2 earl-tars w—f—m» 3- new ester +a1£ohol 1‘ CH 25!" - afiuse cold so 2 0/ 0/ + H0614; ~Hna+gou do 2‘ Hsoz’dfizo min-{sk— *c" - \n dw aim fl pEDMLZA‘ in+o _ cwboxgu‘c mad 2. Mixed Claisenw— Same. MEChant‘sm as above - Com be, Cow:de using same mama as mixed aldoi - Q) use es+ev~ wi-Hn md-MgdemS in EXCESS Q2) add 2‘” eereM slvuflj (low Wcm‘m3 Nflou (10m (56+ dig§erm+ mix—rum; 0:?- veaoMnh: (D diesw + es+ex --+ new diam —r (Masha (COWbMad-é 3.\vah0\ew\wv Ems: a) Ckaisem Condensom‘oxn‘: (DiecKmamm Condensafion) 5 mmbwedl vfng 5 “ U0 dieswsrs ° ‘27“ .——--—-v (a ww-Weck vfngs Wee/h. ExamBLz: medaEXmELe! a»; 4 3 . H ‘ H 24 u ‘4 H29 p” 5st C) Th? Robinsm Annulafiion: J 7 (K , 60H H659 H10 ‘ m i that 2/1 | anemtw Ho chfiicm M010! adofifih‘am My aim;an H10"? Q ngosefl Had/1 (Ame did NOT do VHS, \aud' you may 0M OJ} Wm!) - ‘ 5 6Q ~50 0' my W.» 9/ H . ‘ H H 63d H (michaeD (9.; ‘x . 63:? QH HzO 90H (dim'madfm) 14"" (EH H0; . I “CDQ/ Acids -— Dewboxglwfim (43on C02 Ll) 3*Ox0cwvboxglic @ as occurs WM; cwbaxglcde Ems are Carboklei‘c chords 3—mu/bmr <Frvm l 5am, Cmdifims: a, Wong (3', .. C n q WWMS-FOV 5’ WESWM 33> Symhesfm cmboxglr‘a Add; - Chm s s+wr+ wf-Hn Nekhw matched-e. : a4: .. C? I cum OM04 we W: Rflw /é‘*oH + COL 3 2' L a Z.P\—-Ev* 2' 3 Hgo’K 2 Mach 1. A23; ‘ $3.}? 960 u Q‘Efiwawg 5+0 koa M 960 oat .. - 3' HBUtHzO A (mamas) 3% gm cam add +wo R‘ SYDULPS by adding aWW mng “GUM . WW9 adding w aad,.wa+w and Mad": ‘ W 1 Oxidafionv-Reduafim I L - HX bnds Xchalngw) 0990ng ‘Y-‘CaHbmdw €43,0ch v C Veguwm Redudion: I 1 mm or 01¢ng __._..3:_._. Guyana Pkbpd “’1’ KNOW Lindw cmixjm am WAS using Nari, NHSCU‘Q _ NI - ‘ +0 2. heme or Magma muffin“, odw‘mfl - Karma Ni 6X. 14 0H ' X Rang-3M /‘\ 3.xMWMs wW M achOWIS I or aafi hW‘w 7"st 0r i-Li‘MH‘4 H30"? ‘ - . - Weade _ My, god? WNW ‘93 ngs Cb X Read Wugh AM (k? \‘M 21’“ Md mad .3 Mm. Oxidafion: . when oxfdil‘ae ' 2" alcohols —-—-9 W5 d anal/101$ M Kaunas waiotbhydm D (LhapW IO3 565va 10.5 'iH ‘CrOs- H 0 . D 0 We C9aflw~ W} H H«- / O a: 000$: OH '9?“ C“ ‘ w- -" F‘- nun- HowCr: + (>20 W a " emu- 0 I? OH 11 HRS 0 ® 0 0 H304“ ‘mewhi ex. Pn‘mwno Admin»! 04sz are; H £319.?» ' 0H can”? 5*”? gate/«3% \fin w Oxrdajw‘m ( ms) +1200 (xv/bomb! add M W 3 WW chox Ls‘c 0.0151 63W I} ‘ W ’FW (HM W] EKG/0‘44 “@MM W :"H 69 H fl? M C Owo U “'13 Hgdwxylach‘m ac? A’Mem (16(5) W KMY‘OL‘H Ho‘- 5mm M waw (£01 (2 cold 0 , CX-l N M N H 9x2. 0H ' - 0H ' 0H 942.2. mum, HO" “' am 1-050” VIC/MM oho' 2. MWM 3 2 Myth 6X. 9 wit—u» 0 )‘l H V“) WWW/f abut/Li Wot/Leuw‘i‘ms mass 1 (NOW H4, 2) 2n) W» 25 (0913313 9; H'LO'L. ‘ W ox‘jU‘c CLOL‘GLS 003 [>035 “3430C? ex‘ M $34,292, Ho + og< 2) (was H CWX N. “E 1 an? I) 03)"?806 W 7/) %,HLO ...
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This note was uploaded on 04/07/2008 for the course CHEM 109B taught by Professor Aue during the Winter '08 term at UCSB.

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Chapter 18 Final Packet! - Chapter 18 Packet: Final CHEM...

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