1、第十六章8二羰基化合物自測題答案O命名下列化合物，卜ch3-HGCHCHCHCOOH CH3CH2COCH2CHOO-II/ Y -戊酮酸(3) L日二甲基丁魄 4-戊二酮皿如氣ECCHCiFIjOHH+ IICH3C-OC2OII豚QN&2再。一QQ死-(2) CHjCOOH0QE*GH我一。QH(以下同)0II解：先合成乙酰乙酸乙曹WQ) CH30HoIICT3C- CII2C- OC2H50IICaHjONa4O 0CH5I II II A CJ13C-CHC-OC2H5Cff3l o 。ii iich3c- chc- oc2h50 H 0廠Ii c-c-c-ocjCHSoT件如七悠_虹

2、產(chǎn)-ch3。亞0颯1 IICH3C_C-C-OCch3Q) u-e穗矩一是二一己酮還原得封的。而0(-眺甌I懿是丙酮的任-正穗取代物即用 乙酰乙酸乙坊和正畫基避反應(yīng)，巍虱撅得口-己酮。 正醴熨I由所給的甲醇和乙醇變化而得。-CH3OH h2c=o,HErMgCH3CH2OHC也UH邛f ksA CH3CJ-l2MgBr3 -II酮式分解LJprCHbCH我HQH 擋工 CH3CH2CH2BrQ oQ 。CIi3C- GH3COC3Hj CHC- -WOC2R5 +11盛瞄H0oI2 CH3C-CH-C-QH5 efl H-Ia。悠成電8旦狂CH3C-CH-C-C2H5 丑，-82Q Q(成酮弁

3、解.o Q:0 0:CH3CCH3CQC2Hj + NaH pCCFICOCIlJ Na+ + H礦(此處用域懸底鼬，是為了痘主反應(yīng)中生成電醵照作用g0IIGHf:。OII IICH3CCHCOG2H5COCII30 OII IIa CL13CCHGCH3（四）完成下列方程式。丙酸乙庭+乙二酸二乙虢(I)C 也。H 0)H+CH3CHCOOC2H5COQC2H：50乙酸乙酯+甲酸乙酯OHCCH2COQC2H5 r苯甲酸乙酯卜丁二酸二乙酯P）明。H0IIOCHCH 州 00。2壓:COOC?HS0011II.C日犯頂壓）4。00瓦 C!HQ) H+OOIIIICH3CCH2)3OTQH1)C2H

4、5OH.h+/HqCHwCOQGH ch2：KcH2CH2CQ0C2H5（1）彳奶COOCHI CH3 CH2 O OC CH2 CH2 CH ch CH3 Q)h+COQCjH0 CH3COOC2H5 *（五）用丙二酸二已酯合成下列化合物。CH3CH-CHCOOH1 I、C電 ch3HOOCCH2GHCH2CH2eQOH1，J CH-iCOOHHOCCH3CHCH2COOHCOCH解:pj-目標(biāo)分子可看作是乙酸的-CFI3和ch3ICH- CH?CH2(COOC2H2七CH3CH(：C0OC2H 業(yè)一七 5%hTaOH(CH由汨+(ch3)30hc(cooc2h5)2 M cch3)2chc

5、hcooh HYPERLINK l bookmark67 o Current Document Lt(3) A ?-CO21ch32ch3Q)目標(biāo)化合物為IQ-二舞基化臺枷 可經(jīng)Michael加成制得.，CH2(COOC2H5)2 CHjObU 伊型8改 * CH3CH CHwCOQSH.CH(SQ0H 由fl) NaOH/Hp: H十CH3CH- CHjCOOH0)48 廣CI-12 CO OHHOOCCH2CHCH2C.OOHch33）：分析:JllOOCCH2CH-CH24cH2r)OH!L1|LH來自“丙二” CH3 來自*丙二HBr Hr 2CH3Na.OH/Hp(H5OOC)2CH

6、 - CH- CH2CHOOO UCHHOQCCH2 - CH- CH2 CT2COOHIpCH3目標(biāo)優(yōu)合物是內(nèi)釀應(yīng)先制備4-戊酮酸酩卜OH= CH3CHCH2a-I2CQOH內(nèi)酢廿羥基酸0II :CH3C-CH2ch2cooh： .LI“兩二上浸代廊同OII答案： cc廠 tt、 C2HjO-Na+ CH5COCH2BrCH2(COOC2H2 CH3CCH2CH(COOC2H5)21) NaQH/HpoII*- CHi Q CH7CH2C O OH6，g-OH電何.CH3CHCH2CH2COOH或看:nCH2(COOC2H5.C2HjQMa CH-(COOH5)2W 瀉 .、V CH3-CH

7、CH2CHCCOOC2H5)- I.b(L) NaH/Hp.H 十CH3CHCH2CH2COOH h+_百E*品 一必頊d。(5)目標(biāo)分子可看作乙酸的二烷基取代物:來自丙二BrBr 55 WQ吒晶伽奶”H,CQOC2H5+JCOOC.2H5(I) NaOH/HpH+(3) A , -COCOOH2CH2(COOC2H5)2 沖2CH-(COOC2H5)2Na+2 r H B c-2 r H E cBr-CH2-Br(CSH5O.0.G)2CH-CH2CH2-CHCC0OC2H5 a (l)NaOH/HO c2h5 0 e、八 co。詛5 h+ _ c2h51ch-2O QHQ)H+ch2(ch

8、3)2ch3 一0COOC2FI5?CH3MgI一 H+xcooc2h5北 h3 JJ OH N1, ACOOC2H5 hCaHOHMichealiO 成oIICH2H2CCH2CH34-1CQOC2H5CHMaOH A Rcjbig皿增環(huán)CQOC迎CQOC2HjPh舟如Vetting 反應(yīng)ch3a。Ocaoe沮 5 poIIS電C。沮土 CH2CQOG2H； cONa)CH2C-O.C2H5 + 喪80渺c2h5ooc-Lo。COOC2H5(b)CH+CO0QH5COOCjHjI COOCHJ 孑夕COOC3H5COOC2H5(L)5%NaOHQ)h*(一8 廣 CHKCC田QQQG%0C4

9、I5O- CjHjBt IIA - CH3OSHCOoe jH50 CH3COOC2H5BiCHCOOCoHj II I- CH3 C- CCO0C2H5 .g2h50酮式分解IICH3C - CHCH2COQC3H5+JC迎OH OHi I I 00CH2CH2、 /2CH3Mrf干 HC1 CH 我- CHCH3GOOC2H5Q迎O OHHQ III市* CHK-CHCHCCH/女瓦 CH3OHOHIIch3chchch2cch3+-c 沮5 CH3oCH.ONaII、二丑 EtpCCHac玦CHQOOEt)廣L- ri i；UH CH3： 4-，hCH2COO.C2H511廠 3扣&11

10、 CECHCN0 七8。萍 , 廠 CN 而虻 f/cOOC2H5 “Mi che al加成 一(lJ%bTaOH&H +CHCHsOTOOOIIHYCsHsO-NaII IIeH3COOH3CO.aH5 + ch3ccc3h5-r-. ch,cchc-ch3 中c6qc2(ip%NaOHH+(3) A,-CO3II IIA CH3CCH2CCH3O OCjO PfcCHBr |*- ch3cchcch3CH2Ph| 十 CH2O.HClAZnCl；65jC.產(chǎn)fGE0C1 NaCN0(2)trCH2COOC3H5 廣廠 CH次fHCCOC沮* 5%NaOHOII 廠CH犯。也一|NaNH2CHCHCHnBrCH三 CH d CH三如一-一& 出 * C電食理CH；C三 CH# TOC o 1-5 h z H+/H2OO00ch3coch2ch3ch3cchch3 心1* CH3CCHCH34JCBrHOH& - CH3CH