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1、 C OHO C O OR H H OR H O HC C R COOH OH2 R COO H3O-+ + Ka R COO H3OR COOH= + - RCOOH H2CO3 OH H2O ROH RC CH NH3 酸性增強(qiáng) COOHCOOH NaOH COONaCOOH COONaCOONaNaOH草酸氫鈉 草酸鈉 R OOR OO R OOC - 1/2-1/2-C C H OOHC0.120nm 0.134nm ClCH2COOH ClCHCOOHCl ClCCOOHClCl2.86 1.26 0.64 HCOOH CH3COOH CH3CH2COOH CH3CH2CH2COOH
2、3.77 4.74 4.87 4.82CH 3CH2CHCOOHCl CH3CHCH2COOHCl CH2CH2CHCOOHCl2.84 4.06 4.52 FCH2COOH ClCH2COOH BrCH2COOH ICH2COOH2.66 2.86 2.86 3.12 COOH O H O OCOOH OH C 1/2- 1/2- COOH COOH NO2 COOHNO 2 COOH CH3A B C D 2 R C OHO M gO (RCOO)2M g H2ORCOOH NaOH RCOONa H2O 溶于水,遇酸還原為原來的羧酸堿金屬鹽RCOOH Na2CO3 RCOONa H2O
3、CO2 R C OHO PCl5 R C OCl C OHORP2O5 OH2 R C OC OR O ROH-H2O R C O OR NH3 R C ONH2 酰鹵 ( ) 酸酐 加熱 酯 酰胺 酰基 R CO OHR CO O H P2O5 R C OCR OO RCOONa Cl CO R R C O C RO O NaClCOOHCOOH CC OO O鄰苯二甲酸酐 R CO OH SO2Cl2 R CO Cl SO2 HCl76 C0bpR CO OH R CO Cl HClPCl5 POCl 3162 C0R CO OH R CO ClPCl375 C 03 3 H3PO3 R
4、CO OH H O R 濃H2SO4 R C ORO H2O有機(jī)酸酯 R CO OH H+ R C OHOH ROH R C OHOHO RH R C OH2OHOR H2O R C OROHH+ R CO OR COOHCOOH ROH COORCOOH ROH COORCOOR R CO OH NH3 R CO ONH4 H2O R CO NH2 H2O R C N腈羧酸銨鹽R CN H2O R CO NH2 H2O R CO ONH4 CH3 CH CH COOH LiAlH4 CH3 CH CH CH2OH分子中的雙鍵不受影響 CH3COONa NaOH (CaO) CH4 Na2CO
5、3CH 3 C CaO CH3CO OO CH3 CO CH3 CaCO3CH 3 CO CH2 COOH CH3 CO CH3 CO2 + 加熱 + 加熱 + 加熱 + COOHCOOH 150C0 CO2 HCOOHCH2 COOHCOOH CO2 CH3COOH CH2CH2 C OHOC OHO C OOC O H2O丁二酸酐(琥珀酸酐) CH2 CH2COOHCH2COOH OCC OO C H 2C H 2 C O HOC O HOC H 2C H 2 O C O 2 H 2OB a(O H )2CH2 CH2 C OHOC OHOCH2CH2H2C Ba(OH)2 O CO2 H
6、2O CH2COOH Cl2 CH2COOH Cl2CHCOOH Cl3CCOOHCl2 Cl2H ClP P P CH3COOHCH 2COOHOH CH3CH2COOHCH 3CHCOOHCH 2CH2COOHOH OH 4.763.85 4.873.86 4.51 R CH OOH OH RCHO OHOH R CH OO O RCHOC C CC CH CH OH OHR OH CH CH O OHR C 稀 OH - H+稀或 C CH CH OH OHR OH CH CH O OHR C 稀 OH - H+稀或 C CH2 O OHCH2 CH2 OH O OC CH2CH2 OO
7、HCH2CH 2 OH OOC HO(CH2)nCOOHO(CH 2)nCO OHH OH2+ m (m-1) R CH COOHOH RCHO HCOOHRCHO CO2 OH2KMnO 4R2COOH CO OH2H2SO4KMnO 4H2SO4 + + +稀 CO2 OH2KMnO4R2C COOHOH O H+ R2CO + R CH COOHBr RCHO HCOOHOH2H 2SO4 R CH2 COOH Br2PR CH COOH OH +稀 OH - CO2KMnO4R CHCH2 COOHOH R CCH2 COOHO RCCH3OOH- - R C XO R C OO R
8、C OO R C NH2OC RO R. . . . R O L R O LNuC + Nu-: : C: - R O LNu R O Nu LC: - C: +:- R C ClOR C OCO R C OOR C NH 2O OR R H OH R C OOH ClHR C OOH R OHNH 3 + + R O L R OH LH+ HOH R OH LOH2R OH L OH2 R O OH HL H+ C +: C + C+C C: + R O L R O L LR O OHOH OH OH R O O OH 2 C + -: :C: - : :- C: - C -+ R CO O
9、H H+ R C OHOH ROH R C OHOHO RH R C OH2OHOR H2O R C OROHH+ R CO OR R C ClOR C OCO R C OOR C NH 2O OR R H OR R C O ClHR C OOH R OHNH 3 OR+ + C25H51COOC26H53 C2H5OH C2H5ONaC25H51COOC2H5 C26H53OH+ +C25H51COOC26H53 C2H5OH C2H5ONaC25H51COOC2H5 C26H53OH+ + O OOH CH3 ClO Cl OCH3 O OC C+ C C R C ClOR C OCO R
10、 C OO OR R H NH2 R C O NH4ClR C OONH 4R OHNH2+ + R C NH2O NH3R NH2R2NH R C O NHRR C ONR2過量過量 + R C ClO RMgX C ClROMgXR -MgXCl R C RO OH2 RRR OHR C RO RMgX CR OMgXR R C + R C ORO RMgX C ORROMgXR -MgXCl R C RO OH2 RRR OHR C RO RMgX CR OMgXRR C + + MgICH 3O CH2 COCH2 CO O CH 3O CO CH2 CH2COOH+ 41% R Cl
11、OCR OC R OROC LiAlH4 RR R CH2OHCH 2OHCH 2OH ROH R C OO +2 R NH2OCR NHROC R NR2OC RR R CH2 CH2 CH2 NH2NH NR2 RLiAlH4 R C N HO H. CH3 C NH2O Na CH3 C NHNaO H+ +1/2 2乙醚CH3 C NH2 O ClH CH3 C NH2O ClH+ . CH2 C NHOCH 2 C O KOH CH2 C NKOCH 2 C O OH2+ 無水 乙 醇 + CH3(CH2)4 C NH2O SOCl2 CH3(CH2)4 CN SO2 ClHC 6H
12、5 C NH2O P2O5 C6H5 CN H3PO4 + 加熱 + + 2約86+ 加熱 + 約73 R C NH2O Br2 NaOHR NH 2 NaBr Na2CO3 OH2 + + 4 + + +2 2R C NH2O Br2 NaOHR NH2 NaBr Na2CO3 OH2+ + 4 + + +2 2 RCH2 C OOC2H5 H CHR C O OC2H5 C2H5Na RCH2 CHR C O OC2H5C O C2H5OH+ + 酮式95 烯醇式7 .5%(與Na反應(yīng),與溴的四氯化碳溶液反應(yīng),三氯化鐵顯色)CH3 CO CH2 CO OC2H5 COH CH C OC2H
13、5OCH3 乙酰乙酸乙酯的脫羧 乙酰乙酸是酮酸的代表,在低溫下穩(wěn)定,室溫以上,即失羧而成酮這是酮酸的共性。 CH3CCH2COOHO CH3CCH3O + CO2CH3 CO CH2 CO OC2H5 ClCH2COOHNaOH ClCH2COONa NaCN CH2COONaCN C2H5OHH2SO4 CH2 COOC2H5COOC2H5 丙二酸二乙酯的ClCH 2COOHNaOH ClCH2COONa NaCN CH2COONaCN C2H5OHH2SO4 CH2 COOC2H5COOC2H5ClCH2COOHNaOH ClCH2CO Na NaCNCH 2COONaCN C2H5OHH
14、2SO4 CH2 COOC2H5COOC2H5 ClCH2COOHNaOH ClCH2COONa NaCNCH 2COONaCN C2H5OHH2SO4 CH2 COOC2H5COOC2H5 丙二酸二乙酯的 CH2(COOC2H5)2 C2H5O Na Na CH(COOC2H5)2 C2H5OHNa CH(COOC 2H5)2 RX RCH(COOC2H5)2 NaOHOH2RCH(COONa) 2 H+ RCH(COOH)2 CO2 RCH2COOH + - + + -+ - - 加熱 O OH - O - C6H 5CH =CH CO C6H 5 O CH CH 2CC6H 5OC6H 5 CH 2=CH C CH 3O + CH 2(COOC2H 5)2 C2H 5ONaC2H 5OH CH 2 CH 2 C CH 3OCH (COOC2H 5)2