unsaturated ones, can be synthesized from carbohydrates and c All of the saturated triacylglycerols of the body, and some of th proteins 23.2C SAPONIFICATION OF TRIACYLGLYCEROLS Alkaline hydrolysis of triacylglcerols produces glycerol and a mixture of salts of long-chain carboxylic acids H2C-OH RCOO- Na H2C-O-C-R H,O t naoh HC-OH t RCOO Na HC-0-C—R HOC-OH R"COO Nat H,C-0-C-R Glycerol Sodium carboxylates (丙三醇) (羧酸钠盐)
All of the saturated triacylglycerols of the body, and some of the unsaturated ones, can be synthesized from carbohydrates and proteins. 23.2C SAPONIFICATION OF TRIACYLGLYCEROLS Alkaline hydrolysis of triacylglcerols produces glycerol and a mixture of salts of long-chain carboxylic acids. H2 C HC H2 C O C R O C R' O C R'' O O O H2 C HC H2 C OH OH OH + RCOO - Na + R'COO - Na + R''COO - Na + Glycerol ( 丙三醇) Sodium carboxylates (羧酸钠盐） + 3NaOH H2 O
These salts of long-chain carboxylic acids are soaps and this saponification reaction is the way most soaps are manufactured Soaps are almost completely miscible with water. Soaps micelles in water are usually spherical clusters of carboxylate ions that are dispersed throughout the aqueous phase with their negatively charged carboxylate groups at the surface and with their nonpolar hydrocarbon chains on the interior Thus soap solution are able to separate the dirt particles because their hydrocarbon chains can"dissolve in the oil layer Synthetic detergents function in the same way as soaps; they have long nonpolar alkane chains with polar groups at the end
These salts of long-chain carboxylic acids are soaps and this saponification reaction is the way most soaps are manufactured. Soaps are almost completely miscible with water. Soaps micelles in water are usually spherical clusters of carboxylate ions that are dispersed throughout the aqueous phase with their negatively charged carboxylate groups at the surface and with their nonpolar hydrocarbon chains on the interior. Thus soap solution are able to separate the dirt particles because their hydrocarbon chains can “dissolve” in the oil layer. Synthetic detergents function in the same way as soaps; they have long nonpolar alkane chains with polar groups at the end
CH3(CH2),CH2S0,0 Na* CH3(CH2)nCH2OSO20Na Sodium alkanesulonates Sodium alkyl sulfates (烷基磺酸钠盐 (烷基硫酸钠盐) CH Na oo,s CH(CH2)nCHyCH3 Sodium alkylbenzenesulfonates (烷基苯磺酸钠盐) Synthesis of detergents offer an advantage over soaps; the ley function well in "hard water 23.2D REACTIONS OF THE CARBOXYL GROUP OF FATTYACIDS
CH3 (CH2 ) n CH2 SO2 O - Na + CH3 (CH2 ) n CH2 OSO2 O - Na + CH(CH2 )nCH2 CH3 + Na - OO2 S CH3 Sodium alkylbenzenesulfonates (烷 基 苯 磺 酸 钠 盐 ） Sodium alkyl sulfates (烷 基 硫 酸 钠 盐 ） Sodium alkanesulonates (烷 基 磺 酸 钠 盐 ） Synthesis of detergents offer an advantage over soaps; they function well in “hard” water. 23.2D REACTIONS OF THE CARBOXYL GROUP OF FATTY ACIDS
Fatty acids undergo reactions typical of carboxylic acids. they react with lialh4 to form alcohols. with alcohols and mineral acid to form esters, with thionyl chloride to form acyl chlorides (I)LiAIH4, diethyl ether RCHCHOH (2)H2O RCH,COOH RCH2 COOCH3 SOCI Pyridine RCHOCOCI 232E REACTIONS OF THE ALKYL CHAIN OF SATURATED FATTY ACIDS Fatty acids undergo specific halogenation when they are treated with bromine or chlorine in the presence of phosphorus
Fatty acids undergo reactions typical of carboxylic acids.they react with LiAlH4 to form alcohols, with alcohols and mineral acid to form esters, with thionyl chloride to form acyl chlorides: RCH2COOH (1)LiAlH4 , diethyl ether (2) H2O CH3OH, H + SOCl2 Pyridine RCH2 CH2OH RCH2 COOCH3 RCH2COCl 23.2E REACTIONS OF THE ALKYL CHAIN OF SATURATED FATTY ACIDS Fatty acids undergo specific halogenation when they are treated with bromine or chlorine in the presence of phosphorus
RCH COOH *(1)X2, P4 RCHXCOOH HX (2)H2O 232F REACTIONS OF THE ALKENYL CHAIN OF UNSATURATED FATTY The double bonds of the carbon chains of fatty acids undergo characteristic alkene addition reactions NB CH3(CH2)nCH2-CH2(CH2)mCO2H CH3(CH2),CH=CH(CH2)mCO2H CCl4 CH3(CH2), CHBrCHBr(CH2)mCO2H (2)NaHSos-CH3(CH2)nCHOH--CHOH(CH2)mCO2h HBrCH2(CH)CH2 CHBr(CH2)mCO2H CH3(CH2 ), CHBrCH2(CH2)mCO2H
RCH2COOH + (1) X2 , P4 (2) H2O RCHXCOOH + HX 23.2F REACTIONS OF THE ALKENYL CHAIN OF UNSATURATED FATTY The double bonds of the carbon chains of fatty acids undergo characteristic alkene addition reactions. CH3 (CH2 ) nCH=CH(CH2 )mCO2H H2 Ni Br2 CCl4 (1) OsO4 (2) NaHSO3 HBr CH3 (CH2 ) nCH2 CH2 (CH2 )mCO2H CH3 (CH2 ) nCHBrCHBr(CH2 )mCO2H CH3 (CH2 ) nCHOH CHOH(CH2 )mCO2H CH3 (CH2 ) nCH2CHBr(CH2 )mCO2H CH3 (CH2 ) nCHBrCH2 (CH2 )mCO2H +