大一课件一下有机化学ch10acids and substituted

OrganicforStudentsofMedicineandMay13,ChapterCarboxylicSubstitutedAcidsCarboxylic羧基（－COOH）Carboxyl酰酰ROC羧ORHOHHCOMMONO CH3CCH3CAcetic

FormicOCH3CH2CH2COHButyricOC

Benzoic CCH3CHClactic salicylicO (CH2)16 stearic

phthalicCommon CitriceeoicO MethanoicacidIUPACO HC (α-methylbutyric

Butanedioicacid(Succinicacid)

(maleicacid)

(Fumaricacid)延胡索酸或富HOCyclopentanecarboxylicHOBenzenecarboxylicAqueous H H由于羧酸能与水形成氢键,甲酸至丁酸与水互溶(Formhydrogenbondswithwater沸点:

R-

O之间形成两个氢键,缔合成稳定的二聚体.(exist PreparationofCarboxylic

PreparationofCarboxylicR-

COH

ROCOROCOROC H+, ChemicalHOO O

H

SubstitutionOCOOOCO Whyareacids

10-CH3COH

O

10-ResonanceResonanceStabilizedCarboxylateOOO1O

O O OCO负电荷通过p－OCO EffectofStructureon

1.8x10-1.3x10-1.4x10-1.3x10-2.1x10-取代基诱导效应对酸性的影 供电使负离子不酸性

吸电使负离子酸性苯甲酸的酸性比甲酸弱，比其他脂肪族一强BenzoicH

6.3x10-4.2x10-1.4x10-3.8x10-o－m－p－ <

的酸二元羧酸的酸性大于相应一元羧酸A乙酸碳酸乙醇C碳酸乙酸苯酚

Salt ＋

＋H2R-+No应用+Na+Na+Na

COO COO

COO COO COOFormationFormationofDerivativesofCarboxylicAcidsFormationofacidPX3,PX5（X=Cl,Br),

FormationofacidO一元酸 RC

R 二元

R OH230℃ 混合O

OH

CH3CH2COCCH3Formationof

酯化反应可逆,可采取使一种原料过量,或反应Heatmixtureofcarboxylicacid,alcoholandsulfuricacidunderOOC6H5-

C6H5-

O

C6H5-C-

C6H5-C- C6H5-

C6H5- -C--C-O

CH3COOH+CH3CH2OH +(4)Formationof

-H

RCOONH4

C 190℃

DecarboxylationofMonocarboxylic反应,称为脱羧反应.①羧酸碱金与碱石灰共融脱羧生成烃 NaOH(CaO)②一元羧

CH4 NCO3当α-碳原子上连有吸电基时,NO2、

OCl等,较易脱羧

△ DecarboxylationofDicarboxylic HCOOH+ CH3COOH+O

脱(-

+ 脱 O

+O H2O++OH2O+脱羧反应是生物O C

脱羧酶

CO2, C2H5OH,CommonFormicacid,aceticIUPACMethanoicacid,ethanoicacid,butanoicAnion O

+

FormationofcarboxylicacidRCOOH+

RCOOR'+SubstitutedCarboxylicHydroxy

AlcoholicacidPhenolicacid3-Hydroxypentanoic

-2-Hydroxybutanedioicacid(malicOHCH3CHClactic

Citric(salicylicacid)邻羟基（水杨酸

(gallicacid没食ChemicalPropertiesofHydroxy

问问题-I-I使酸性增强，+C

子诱导效应因间隔三个

aabb羧基中 H的极性，离解后的质 O

-

O+OxidationReactionofAlcoholicO

稀HNO3

COOH稀 CHCH2COOH

H3CCCH2COOH COOH+ODehydrationofAlcoholic-HydroxyH H

H H

+O

n

OCH 聚丙乳酸，对无害。如果这种聚合物中混有某种药CH3HOCHCHCH222OOO

O

γOOOOOO*OOO

具有扩张冠状作用的药DecarboxylationofPhenolicKeto-Keto-OCH3CPyruvicO

α CH3C β–丁酮酸（乙酰乙酸β-Ketobutyricacid(acetoaceticO C 丁酮二酸（草酰乙酸Ketobutanedioicacid(oxaloaceticChemicalPropertiesofKeto-OCH3C

CH3C

DecarboxylationofKeto-αα–Keto-RCOCOOH 试 +

稀 RCHOOCH3

稀

β–Keto-acids R OC RO酮式分O

OHO

C酸式分OCH3C

O +Ketonebodiesinclinicalβ–Hydroxybutyricacid,β–KetobutyricacidandAcetone

H3C -

H3CC

0.8-5mg之间，一昼夜随尿液排出 Acidityofhydroxyacidsandketo-acidsDehydrationofAlcoholicAcidsDecarboxylationofKeto-AcidsKe