Nomenclature Of Carboxylic Acids
Chapter 5 Carboxylic Acids and EstersCarboxylic Acids Carboxylic acids are weak organic acids whichcontain the carboxyl group (RCO2H):Chapter 5Carboxylic Acids and EstersOOCCOHOa carboxylic acidCChapter Objectives: Learn to recognize the carboxylic acid, ester, and related functional groups. Learn the IUPAC system for naming carboxylic acids and esters.R Learn the important physical properties of the carboxylic acids and esters. Learn the major chemical reaction of carboxylic acids and esters, and learn how topredict the products of ester synthesis and hydrolysis reactions. Learn some of the important properties of condensation polymers, especially thepolyesters.OHRCOOHRCO2Hcondensed ways ofwriting the carboxylgroupHOthe carboxyl group The tart flavor of sour-tasting foods is often causedby the presence of carboxylic acids.Mr. Kevin A. BoudreauxAngelo State UniversityCHEM 2353 Fundamentals of Organic ChemistryOrganic and Biochemistry for Today (Seager & ure of Carboxylic Acids Select the longest carbon chain containing thecarboxyl group. The -e ending of the parent alkanename is replaced by the suffix -oic acid. The carboxyl carbon is always numbered “1” but thenumber is not included in the name.Nomenclature ofCarboxylic Acids Name the substituents attached to the chain in theusual way. Aromatic carboxylic acids (i.e., with a CO2Hdirectly connected to a benzene ring) are namedafter the parent compound, benzoic acid.OCOH3Examples: Naming Carboxylic AcidsExamples: Naming Carboxylic Acids Name the following compounds:O Name the following compounds:OOBrHCCH3OHC4Benzoic H2COHCH3OCH3CHCH2COHCH2CH2CH356
Chapter 5 Carboxylic Acids and EstersExamples: Naming Carboxylic AcidsExamples: Naming Carboxylic Acids Name the following compounds: Name the following compounds:CH3OCCH3 OOHCH3CCH3CCHCH3COHCH37More Complicated AcidsCCOHOHOOCCCCH3CHCH38OCH2CHCH2C– 4,5-dimethyl-3-nitrooctanoic acidOHCOCH2Cl– 2,2,5-trimethylhexanoic acidOHethanedioic acidOH Draw structural formulas for the following molecules:– 2-methylpropanoic acid For molecules with more than two carboxylic acidgroups, the carboxyl groups are named as carboxylicacid substituents.OCExamples: Drawing Carboxylic Acids For molecules with two carboxylic acid groups thecarbon chain in between the two carboxyl groups(including the carboxyl carbons) is used as thelongest chain; the suffix -dioic acid is arboxylic acidpropanedioic acid9101112Examples: Drawing Carboxylic Acids Draw structural formulas for the following molecules:– para-bromobenzoic acid– 2,4,6-trinitrobenzoic acid– 4-ethylpentanedioic acid(what’s wrong with this name?)
Chapter 5 Carboxylic Acids and EstersPhysical Properties of Carboxylic Acids Carboxylic acids hydrogen bond to themselves toform a dimer:ORPhysical Properties ofCarboxylic AcidsHOCCOHRO Carboxylic acids also form hydrogen bonds towater molecules:HHOORCHO13HOHPhysical Properties of Carboxylic AcidsPhysical Properties of Carboxylic Acids Since carboxylic acids can form more than one set ofhydrogen bonds, their boiling points are usuallyhigher than those of other molecules of the samemolecular weight (MW). As the number of carbons in a carboxylic acid seriesbecomes greater, the boiling point increases and thesolubility in water decreases. Many carboxylic acids that are liquids at roomtemperature have characteristically sharp orunpleasant odors. Low-MW carboxylic acids are generally liquids atroom temp. (often, they are somewhat oily); higherMW carboxylic acids are generally waxy solids.– Ethanoic acid/acetic acid is the main ingredient invinegar. Carboxylic acids with 12 to 20 carbon atoms areoften referred to as fatty acids, since they are foundin the triglycerides in fats and oils (more later).– Butanoic acid is partially responsible for the odorof locker rooms and unwashed socks. Short-chain carboxylic acids are also generally moresoluble in water than compounds of similar MW,since they can hydrogen bond to more than onewater molecule.– Hexanoic acid is responsible for the odor ofLimburger cheese.15Table 5.2CommonNameFormic acidAcetic acidPropionic acidButyric acidValeric acidCaproic acidCaprylic acidCapric acidLauric acidMyristic acidPalmitic acidStearic acidBP( C)101118141164186205239270299Dec.Dec.Dec.MP( C)817-21-5-34-3173244586371Solubility(g/100 mL olubleInsolubleInsolubleInsolubleInsoluble Like most acids, carboxylic acids tend to have a sourtaste (e.g., vinegar, citric acid, etc.)16Boiling Points of Various Functional GroupsPhysical properties of some carboxylic H14Figure 5.4The boiling points ofcarboxylic acids comparedto 1 alcohols, aldehydesand ketones, ethers andalkanes.1718
Chapter 5 Carboxylic Acids and EstersComparing Physical PropertiesBoiling Point:Carboxylic : Predicting Physical Properties Arrange the following compounds in order ofincreasing boiling point. (All of the compoundshave about the same molecular weight.)Water Solubility:Carboxylic acidAlcoholsAldehydes/KetonesEthersAlkanes– 1-pentanol– hexane– butanoic acid– pentanalMolecular Boiling Solubility in waterweightpointNamePentane72 g/mol35 CInsolubleDiethyl ether74 g/mol35 CInsolubleButanal72 g/mol76 C7.1 g / 100 mL H2O1-ButanolPropanoic acid74 g/mol74 g/mol118 C141 C9.1 g / 100 mL H2OInfinite Which member of each of the following pairs ofcompounds would you expect to have a highersolubility in water?– 2-butanone or propanoic acid– hexanoic acid or ethanoic acid1920Important Carboxylic AcidsHCCH3OHCCH3CH2OHEthanoic acid(Acetic acid)(from Latin acetum, vinegar)Vinegar is a 5% solution ofacetic acid dissolved in water;acetic acid is also responsiblefor the taste of sour wine (fromthe oxidation of ethanol) andsourdough breadMethanoic acid(Formic acid)(from Latin formica, ant)A component of the venomof ants and caterpillars;produced in the body whenmethanol is consumedSome ImportantCarboxylic AcidsOOOOCH3CH2CH2CCOHPropanoic acid(Propionic acid)Found in Swiss cheese;salts of this acid are usedas mold inhibitorsOOHButanoic acid(Butyric acid)(from Latin butyrum, butter)This acid has a foul, rancid odor;produced from the breakdown ofsoft triglycerides in butterCH3CH2CH2CH2CH2COHHexanoic acid(Caproic acid)Responsible for the odor ofLimburger ricarboxylic acid(Citric acid)Found in citrus fruits (lemons, grapefruit,oranges, etc.); commonly used in bufferingsolutions with sodium citrateOOHOOHOxalic acidFound in many leafy green plantssuch as rhubarb and spinach;combines with calcium ions in thebody to produce insoluble salts,which form kidney stonesOHGlycolic acidAn alpha-hydroxy acid used incosmetics and skin creams;alpha-hydroxy acids are thought toloosen the cells of the epidermis andaccelerate the flaking off of dead skin;however these compounds can increasethe skin's sensitivity to UV lightH2NOHpara-Aminobenzoic aid (PABA)Used in sunscreens; absorbsshort-wavelength UV light. It is also requiredby bacteria for the production of folic acid,needed to maintain the growth of healthy cellwalls; sulfa drugs block the uptake of PABAby bacteria, causing them to be unable tomanufacture folic acid, and thus preventingthe bacteria from multiplyingOHOOHOOOHOOHTerephthalic acidA white, crystalline solid; used inthe manufacture of somepolyestersOHMalic acidResponsible for the sharptaste of apples (genus Malus)23OOHOH2-hydroxypropanoic acid(Lactic acid)Produced from the fermentation of sugarsunder anaerobic conditions; found in sweat,sour milk, fermented pickles, sauerkraut,and yogurt; produced in muscles fromglucose under anaerobic conditions (thebuildup of lactic acid leads to a heavy, weakfeeling, and muscle cramps); produced afterdeath during the breakdown of sugars in thebody by bacteria, inactivating the enzymesthat allow the transport of calcium ions,causing rigor mortis24
Chapter 5 Carboxylic Acids and EstersOOHOOHOOHH2NOHONNiacinA water-soluble, B-Complex vitamin obtainedfrom fish, green vegetables, lean meat, poultry,whole-grain and enriched bread and cereal;produced in the body from tryptophan;essential for growth, healthy tissues, theproduction of energy from carbohydrates, andthe production of fatsTartaric acidFound naturally in wine, and isresponsible for some of the sharp taste ofwine; it is added to many sour-tastingsweet foods. The potassium salt, creamof tartar, has many cooking applications;the potassium-sodium salt, Rochelle salt,is a mild laxative.OOOHOOHOHOHSuccinic acidAn intermediate along thecitric acid cycleFumaric acidOccurs naturally in many plants, and is essential forvegetable and animal tissue respiration; used in bakingpowders, and in some fruit drinks as a replacement forcitric acidOOHO- O NaHOHNH2Monosodium Glutamate (MSG)The sodium salt of the amino acid glutamate;produced in meat during the decomposition ofproteins; with inosine monophosphate (IMP), oneof the major substances responsible for the flavorof meat; MSG is also added to some foods toenhance their meaty flavorPantothenic acidA water-soluble B-complex vitamin;converted by the body intoCoenzyme A, which helps the bodyproduce energy from foodOOONHOHOOHGamma-aminobutanoic acid (GABA)A inhibitory neurotransmitter; ethanol binds to the sameprotein as GABA at a neighboring location, distorting theprotein so that GABA binds more easily, further inhibiting thecell from firing; benzodiazepines such as Valium also bind tothe same protein but at a different site, inhibiting the cell stillfurther, and sometimes with deadly consequencesOH2526Acids and Bases Acids:– have a sour taste.– react with active metals to produce H2 gas.Chemical Properties ofCarboxylic Acids– turn blue litmus red. Bases:– have a bitter taste and a slippery feel.– turn red litmus blue. When they react with each other, acids and basescancel each others properties in a neutralizationreaction:acid base salt water2728AcidsThe pH Scale(H ) An acid gives a protonto another species.Acids produce hydronium ions, H3O , when theyare dissolved in water: The acidity of a solution is measuredusing the pH scale. The pH of asolution is defined asH—A H2O A– H3O pH - log[H3O ] A strong acid is one that completely dissociates inwater (i.e., every molecule of the acid splits apart):H—Cl H2O Cl– H3O A weak acid is one in which only a smallpercentage of the molecules are dissociated at anyone time (in other words, there is also a backwardsreaction, where the acid molecule is regenerated):Acidic:pH 7.00[H3O ] [OH-]Basic:pH 7.00[H3O ] [OH-]Neutral: pH 7.00[H3O ] [OH-]H—F H2O h F– H3O 2930
Chapter 5 Carboxylic Acids and EstersThe Acidity of Carboxylic AcidsThe Acidity of Carboxylic Acids Carboxylic acids are weak acids; in water, theydissociate to produce hydronium ions andcarboxylate ions:OOR The dissociation of a carboxylic acid is a reversiblereaction, and the position of the equilibrium can beaffected by the addition of acid (low pH) or byadding base (high pH):OH CH2ORcarboxylic acidC OOH3Ocarboxylate ionROCH3 H2OCO A 1.0 M solution of acetic acid is about 0.5%dissociated into hydronium and acetate ions:Obase(high pH)Hacid(low pH)carboxylic acidR H3OCOcarboxylate ionOCOH H2OCH3acetic acidCO At the physiological pH of 7.4 (the pH of most bodyfluids) the carboxylate form of most carboxylic acidsis the predominate form.H3Oacetate ion3132Carboxylate Salts Carboxylic acids react with strong bases such assodium hydroxide (NaOH) and potassium hydroxide(KOH) to produce carboxylate salts. Carboxylate salts are named by naming the metalfirst, and changing the -ic acid ending of thecarboxylic acid name to -ate.Carboxylate SaltsORCORC O- Na H2Ometal carboxylateOH NaOHcarboxylic acidbaseOCH333Examples: Carboxylate SaltsOCCC O NaCH3CH2CH2CH2CO- NH4 sodium ethanoate(sodium acetate)34Examples: Carboxylate Salts Draw the structure of pyruvate, the form of pyruvicacid which is found as an intermediate in energyconversion reactions in living organisms.OO- Complete the following reactions and name thecarboxylate salt products.OCCH3OHOHpyruvic acid NaOH Complete the following reactions and name thecarboxylate salt products.OOCH3COHOCCOH NaOHOH KOHCH3CH2CHCH3 NaOHCH33536
Chapter 5 Carboxylic Acids and EstersPhysical Properties of Carboxylate SaltsImportant Carboxylate SaltsO Carboxylate salts are ionic compounds, and aretypically solids at room temperature. Because they contain charges, carboxylate salts aretypically much more soluble in water than thecarboxylic acids from which they are derived.OO- -O Na – This is important in the formation of soaps (morelater).-CH3(CH2)16C2Calcium propanoateCommonly usedpreservatives; foundin bread, cakes, andcheesesOOH NaOH-ONO- Na H2OCH3OC2H5HDenatonium benzoate ('Bitrex')Benzyl diethyl ((2,6-xylylcarbamoyl)methyl) ammoniumbenzoateDiscovered in 1958, this is the bitterest-tasting compoundknown; as little as ten parts per million make substancesunbearably bitter to most humans. It is used as an aversiveagent, an additive that prevents accidental ingestion of atoxic substance. It is used to denature ethanol, methanol,and rubbing alcohol, and well as solvents, paints, arnishes,antifreeze, etc.O- Zn2 2Zinc 10-undecylenateUsed to treat athlete's foot (Desenex)Sodium stearate(sodium octadecanoate)soluble in water OC2H5N CH3(CH2)16CStearic acid(octadecanoic acid)insoluble in waterfound in beef fat andsome butters-O NaSodium citrateThe sodium salt of citric acid, sodium citrate, isused in buffers with citric acid to maintaindesirable characteristics of foams and gels (jelly,ice cream, candy, whipped cream, etc.) bycontrolling the pH of the product; also used inmedicines and blood for transfusions; alsofunctions as an anticoagulant in blood2 O CaCH3OOOO- Na OOSodium benzoateFound in cranberries andprunes; commonly usedas a preservative inbaked goods, ketchup,carbonated beverages,etc.OH-Na OO NaSodium propanoate3738Esters An ester (“carboxylic ester” in the textbook) is aderivative of a carboxylic acid in which there is acarbon group connected to the single-bondedoxygen:OEstersRCOOR'RCOCcarbon groupester linkage3940Nomenclature of EstersExamples: Ester Nomenclature Name the following compounds:ORCacid partOCH3 OR'CH3alcohol partCHCOOCH3HCOCH3 Name the alkyl or aromatic portion contributed bythe “alcohol part” first. The “acid part” is named as a carboxylic acid, withthe -ic acid suffix changed to H3CH2CH34142
Chapter 5 Carboxylic Acids and EstersExamples: Ester NomenclatureExamples: Ester Nomenclature Name the following compounds:OCH3CH2CHC Name the following COCH34344Examples: Drawing EstersExamples: Drawing Esters Draw structural formulas for the following molecules:– methyl butanoate Draw structural formulas for the following molecules:– propyl 2,2,3,4-tetramethylhexanoate– ethyl 2-methylpropanoate– isopropyl benzoate– methyl 2,4-dimethylhexanoate– methyl para-nitrobenzoate4546Important EstersHOOOHHOOHVitamin C (ascorbic acid)A water-soluble vitamin found in citrusfruits; prevents scurvy; essential for healthyblood vessels, bones, and teeth; helpsform collagen, a protein that holds tissuestogetherOSome Important EstersO–OO47OOHONOPeroxyacetyl nitrate (PAN)Produced by the action of sunlight onfragments of unburnt hydrocarbon fuel,oxygen, and nitrogen dioxide; one of theirritants (lachrymator) found inphotochemical smogAmyl acetateAlso known as banana oil and pear oil; thecommercially available compound is amixture of amyl (pentyl) isomersOCH3CH3N OCH3Acetylcholinean important neurotransmitterOOBenzyl acetateoil of jasmine48
Chapter 5 Carboxylic Acids and EstersPolymers with Ester GroupsOOHOOCoumarinFound in lavenderoil, sweet cloverand tonka beansOOOOGeranyl acetategeranium oilOCOOWarfarinA potent rodenticideOONMethyl cyanoacrylatePolymerizes on contact withsurfaces containing traceamounts of water andalcohols to form Superglue;superglue is also used insurgery in place of sutures,and by morticians to sealthe eyes and lips of theirclientsO(CH2)15CH3CH3(CH2)14SpermacetiAlso known as cetyl palmitate; found inthe spermaceti organ or case above theskull of the sperm whale (Physetermacrocephalus). Its exact function is notknown but it may be used as"cushioning," allowing the whale's head tobe used as a battering ram in fightsbetween males (see Moby Dick), as aregulator of the whale's buoyancy inwater, or as an aid in echolocation infocusing sound waves. Spermaceti washighly sought by whalers in the 18th and19th centuries, and was widely used49commercially.OCH3OHMethyl salicylateAlso known as oil of wintergreen and betulaoil; used as a flavoring and as an ingredientin deep heating rubs. It also fluoresces underultraviolet light, producing visible blue light.This is most apparent in Wint-O-GreenLifesavers, which contain methyl salicylateas their flavoring. It is also used in somesunscreen lotionsOOMethyl acrylate (vinylacetate)Polymerizes to form polyvinylacetate; used in acrylic paintsin combination with pigmentsand a surfactant which causesthe polymer to be suspended inan emulsion; also used insafety glass (a layer of PVAsandwiched between twolayers of glass) and chewinggumOMethyl methacrylatePolymerizes to formpoly(methyl methacrylate);trade names are Lucite,Plexiglass, and Perspex;the bulky methyl and methylester groups cause thepolymer to be orientedchaotically within the solidpolymer, allowing light topass through withoutscattering, rendering theplastic transparentLauryl methacrylateUsed to make the polymer poly(laurylmethacrylate); used as an additive inviscostatic engine oils, which keepsthe oild viscous at high temperatures.50OOSynthesis of Esters: Esterification Reactions The simplest way to synthesize an ester is to heat acarboxylic acid with an alcohol or phenol (plus anacid catalyst); the oxygen of the alcohol adds to thecarboxyl group, splitting out a molecule of water inthe process (an esterification reaction).Reactions of EstersOOCH HROOH R'C R' HRan alcoholora phenola carboxylicacidOHOan ester5152Synthesis of Esters: Esterification ReactionsSynthesis of Esters: Esterification Reactions Since this reaction is a reversible reaction, it oftenreaches an equilibrium with a large amount ofunreacted starting material still present.OCR Better yields are obtained using either acidchlorides or acid anhydrides as starting materials.These reactions are nonreversible.OOOCCCO HOacid chlorideORClacid chlorideROCRRacid anhydrideRan alcoholora phenolR' HOCCO HORClOan esterOacid anhydride53CR'ClR'an alcoholora phenolROR' Oan esterHCROa carboxylicacid54
Chapter 5 Carboxylic Acids and EstersExamples: Esterification ReactionsExamples: Esterification Reactions Write both products of the following reactions: Write both products of the following reactions:OCH3CH2CH2COH CH3CH2OHH CH3OCH3COOCOCCH3 CH3CH2OHOHCl 55Examples: Esterification ReactionsExamples: Esterification Reactions Write both products of the following reactions:C Write both products of the following reactions:OOHOCH356Cl CH3CHOOCCH3OH CH3COCCH3OH5758Pain, Pain, Go AwayMore Pain RelieversOOOOHNOHOHSalicylic acidFound in the bark of the willowtree (Salix); a tea brewed fromthe bark reduces fever andrelives pain and inflammation,but is very acidic, and causesirritation of the mucousmembranes in the mouth, throat,and stomach, and can causepainful ulcers and stomachbleedingCH3OHOHOOOCH3OHAspirin (acetylsalicylic acid)Produced by reacting salicylic acid with aceticanhydride, giving a compound which is lessacidic, and does not cause as much irritation,but still retains all of the beneficial medicalproperties; aspirin seems to work by blockingthe production of prostaglandins, hormoneswhich may be responsible for producing pain,fever and inflammation; one of the mostcommonly used pharmaceutical drugs; over 40million pounds are produced in the UnitedStates per yearAcetominophenDoes not cause stomachirritation, and hasanalgesic and antipyreticproperties that are similarto aspirin, but noanti-inflammatoryfunctions; available underthe trade names Tylenol,Excedrin Aspirin Free,Panadol, and Anacin-359OHCH3OIbuprofenAn analgesic, antipyretic,and anti-inflammatorydrug; it is also notirritating to the stomachlining; available under thetrade names Motrin,Advil, Ibuprin, Nuprin, andMediprinNaproxenAn analgesic, anti-pyretic,and anti-inflammatorydrug; active ingredient inAleve60
Chapter 5 Carboxylic Acids and EstersCondensation Polymers: PolyestersCondensation Polymers: PolyestersO Condensation polymers are polymers which formwith the loss of a small molecule (typically water orHCl).HOCH2CH2OHEthylene OOCOCH2CH2OCOH62Reactions of Esters: Ester Hydrolysis Esters may be broken apart under acidic conditionsby water (a hydrolysis reaction) to form acarboxylic acid and an alcohol.OCOOOCCOCH2CH2Oetc.Condensation Polymers: CHOCEthylene glycolTerephthalic acid Condensation polymers, such as polyesters andpolyamides (Nylon, Ch. 6), form when each of themonomers contain two of the same functional group,so the reaction can take place at both ends.OHOCH2CH2OHCCHOCH2CH2 OHnPolyethylene terephthalate(PET)A polyesterOOH ROver 3 billion pounds of PET are made every year. It forms avery linear chain, and is very inert. It can be melted and pulledthrough spinnerettes to make fibers, threads, or yarn (Dacron,Fortrel, Terylene), where it can be used in automobile tire cord,permanent press clothing, sutures, replacements for damagedsections of blood vessels and the esophagus, etc. PET melts canalso be forced through narrow slits to produce thin sheets orribbons known as Mylar; this form is used as the supportmedium in audio and video tape.COR' H2Oan esterRCOH a carboxylic acidR'OHan alcohol This is essentially the reverse reaction of thesynthesis of esters from carboxylic acids andalcohols.6364Examples: Splitting EstersReactions of Esters: Saponification(Because Breaking Up Is Hard To Do) Esters may be broken apart under basic conditionsby sodium hydroxide (lye) or potassium hydroxideto form carboxylate salts and alcohols. Complete the following reactions:OH ORCan esterCH3OOR' NaOHbaseRCO- Na a carboxylate saltCOCH2CH3 H2OR'OHan alcoholOCH3 This reaction is important in the production ofsoaps.65COCH2CH3 NaOH66
Chapter 5 Carboxylic Acids and EstersTriglycerides Long-chain carboxylic acids, often referred to asfatty acids, are stored by living organisms bycombining them with glycerol to produce tri-esterscalled triglycerides. Triglycerides at room temperature are usually eithersolids or semi-solids (fats), or viscous liquids (oils).Triglycerides and SoapsOCH2OHCHOHCH2OHglycerol67Some Saturated Fatty AcidsOHOC(CH2)16CH3stearic acid(a fatty Oglyceryl tristearate (tristearin)a triglyceride68Some Saturated Fatty AcidsOOOHStearic acidA saturated fatty acid found in lard, beef fat,butterfat, cottonseed oil; the sodium salt, producedby heating lard with sodium hydroxide, can be usedas a soapOOHPalmitic acidA fatty acid, found in lard, beef fat, butterfat, and cottonseed oil;the triglycerides in cocoa butter have oleic acid attached to thecentral oxygen, with stearic acid or palmitic acid on the otheroxygens; this more regular composition gives cocoa butter a muchsharper melting point than is usually observed in fats, andchocolate remains brittle almost up to its melting point of 34 C (justbelow body temperature); the sudden melting of chocolate in themouth gives it a pleasant feeling of coolnessOHLauric acidFound in coconut oil;commonly used in soapsOOHMyristic acidA fatty acid found in butterfat,coconut oil, and nutmeg oilOOHArachidic acidA fatty acid found in peanut oil69Some Unsaturated Fatty Acids70Some Unsaturated Fatty AcidsOOOHOHOleic acidAn unsaturated fatty acid; the chain is much less flexible than that ofstearic acid because of the double bond, and cannot pack as tightly,so the triglycerides it forms are oils and not fats; found in olive oil,cocoa butter and chocolate, beef fat, lard, and peanut oilEicosapentaenoic acidA omega-3 polyunsaturated fatty acid found in fish oil and seafoods; omega-3 fattyacids may, according to some studies, help to lower the risk of heart diseaseOOOHOHPalmitoleic acidAn unsaturated fatty acid found in butterfat and cod liver oilLinolenic acidA omega-6 polyunsaturated fatty acid found in linseed oil and corn oilOOOHArachidonic acidAn omega-6 polyunsaturated fatty acid found in corn oil, linseed oil, animal tissuesOHDocosahexaenoic acidAn omega-3 polyunsaturated fatty acid found in fish oil and seafoods7172
Chapter 5 Carboxylic Acids and EstersTriglycerides (Fats and Oils)OOROOOOOOROOOOOC(CH2)12CH3OTriglyceridesfats and oils (lipids)ROROOOOOOTrimyristinFound in nutmeg, a spiceobtained from the seed ofthe nutmeg tree, found inIndonesia and the WestIndies, and other tropicalareasTristearinOne of the principlecompounds in beef fat andcocoa butter; triglycerides suchas this lubricate meat fibers,and make the meat moretender when cooked; theyellow color of beef fat comesfrom carotene dissolved O73OlestraA substitute for dietary fats developed by Procter & Gamble after 30 years and 200 million dollars worth of research; it is a combination of sucrose and fatty acidsobtained from soybean oil and cottonseed oil; it is too hindered for digestiveenzymes to react with; can carry small amounts of fat-soluble vitamins out ofintestinal tract74Fatty Acid Salts(Chewing the Fat) Salts of fatty acids combine two different solubilitycharacteristics: Triglycerides can be broken apart under basicconditions (a saponification reaction) to producelong-chain carboxylate salts.– a long, nonpolar, water-insoluble (hydrophobic)hydrocarbon “tail.”O– a charged, water-soluble (hydrophilic) on of TriglyceridesCH2ONaOH -Na OC(CH2)16CH3 CHSodium stearatea carboxylate ORCH2OC(CH2)16CH3OHOHOHglycerolglyceryl tristearate (tristearin)a triglycerideO Unlike their carboxylic acid forms, the carboxylatesalts are at least somewhat soluble in water.75O- Na Nonpolar, hydrophobic tail(water insoluble)Polar, hydrophilic head(water soluble)CO2- When these substances are placed in water, their“tails” become tangled, thereby dissolving eachother, leaving the charged, hydrophilic portionssticking out into the solution, allowing the wholemicelle to dissolve in water, acting as a soap.Soaps and DetergentsSoap76O(Cleanliness, As They Say, Is Next To Impossible)O- Na Sodium stearateOO- 2Ca2 Calcium stearate"soap scum"GreaseCO2-Sodium Alkylbenzenesulfonatea synthetic detergentSO3- Na Sodium para-Dodecylbenzenesulfonatea biodegradable detergenta soap micelle77OPolyoxyethyleneA nonionic synthetic detergent; causes less foaming.SO3- Na OH78
Chapter 5 Carboxylic Acids and EstersEsters of Inorganic AcidsOROHHOOPH OHROPOHan alcoholOHEsters of InorganicAcidsOHphosphoric acida phosphate ester(monoester)ROORROOHPOHORROPOROHORa phosphate diestera phosphate triester7980NH2Some Important Phosphate EstersNNOCH2O P H2C-ORiboseDeoxyribonucleic Acid(DNA)OHRC NaOHRCROesterR' CCORacid anhydrideH O R'alcoholor phenolCRR' OesterCHROcarboxylic acid6. Hydrolysis of an ester to produce a carboxylic acid and an alcohol.OOH R' H2OCH H O R'C ROROalcoholestercarboxylic acid7. Saponification of an ester to produce a carboxylate salt and an alcohol.OOCR4. Reaction of an acid chloride with an alcohol to produce an ester and HCl.OOH O R'alcoholor phenolNO82R H3OO- Na carboxylate salt OO CH25. Reaction of an acid anhydride with an alcohol to produce an ester and a carboxylic acid.OOOO3. Reaction of a carboxylic acid with an alcohol to produce an ester and water.OOH CH H O R'CR' H O H ROROalcoholestercarboxylic acidor phenolCRClacid chloridePOOH H2OCCH3thymine812. Reaction of a carboxylic acid with a base to form a carboxylate salt and water.OOO Hcarboxylic acidOHNOcarboxylate ionO Hcarboxylic acidNOReactions of Carboxylic AcidsRguanineNO1. Reaction of a carboxylic acid with water to form a carboxylate ion.OO H2OPH2NO CH2OO-NONNOHCOHNOAdenosine TriPhosphate (ATP)RcytosineNNNOPPOO ONNO CH2O-a phosphate triesteradenineOH Cl83OesterR' NaOH H O R'CRO- Na alcoholcarboxylate salt8. Formation of a phosphate monoester.OOH HO P OH R O HRO P OH H2OalcoholOHOHphosphoric acidphosphate monoester84
hydrogen bonds, their boiling points are usually higher than those of other molecules of the same molecular weight (MW). Low-MW carboxylic acids are generally liquids at room temp. (often, they are somewhat oily); higher-MW carboxylic acids are generally waxy solids. Carboxylic acids
4.3 More complex nomenclature systems, 49 4.4 Coordination nomenclature, an additive nomenclature, 51 4.5 Substitutive nomenclature, 70 4.6 Functional class nomenclature, 96 5 ASPECTS OF THE NOMENCLATURE OF ORGANOMETALLIC COMPOUNDS, 98 5.1 General, 98 5.2 Derivatives of Main Group elements, 98 5.3 Organometallic derivatives of transition .
The acylating reagents: carboxylic acid anhydride, acid chlorides, carboxylic acids, esters, thioesters. Classification of poly- and heterofunctional compounds. Polyalcohols, dihydric phenols, dicarboxylic acids, amino alcohols, amino phenols, hy-droxy-acids, oxo-acids (aldehyde and keto acids). Examples. Acid-base prop-erties.
UNIT 12 ALDEHYDES KETONES AND CARBOXYLIC ACIDS 1) What are aldehydes ? 1 Aldehydes are the organic compounds containing carbonyl group,linked with one hydrogen and one alkyl /aryl group. 2) What are carboxylic acids? 1 Carboxylic acids are the organic compounds containing carboxyl(-COOH) group/s 3) Between aldehyde and ketones which one is .
Lithium aluminium hydride will also reduce ketones, aldehydes esters, nitriles, amides, acid chlorides alkyl halides, epoxides and nitro groups Borane reacts most rapidly with carboxylic acids to give primary alcohols and it is possible to reduce carboxylic acids in the presence of some oth
Ch21 Carboxylic acid Derivatives(landscape).docx Page 1 Carboxylic acid Derivatives Carboxylic acid derivatives are described as compounds that can be converted to carboxylic acids via simple acidic or basic hydrolysis. The most important acid derivatives are esters, amides and nitriles, although acid halides and anhydrides are also derivatives (really activated forms of a File Size: 2MB
10 tThe carboxyl group is the parent group of a family of compounds called acyl compounds or carboxylic acid derivatives tEsters are named from the corresponding carboxylic acid and alcohol from which the ester would be made lThe alcohol portion is named first and has the ending -yl lThe carboxylic acid is na
Properties of Acids and Bases Return to the Table of contents Slide 5 / 208 What is an Acid? Acids release hydrogen ions into solutions Acids neutralize bases in a neutralization reaction. Acids corrode active metals. Acids turn blue litmus to red. Acids taste sour. Properties of Acids Slide 6 / 208 Properties
Agile software development with Scrum is first introduced with its elements. Next, we use three development process lenses (communication, coordination, and control) to study how Scrum supports each of development processes, how they are related each other, and how they affect the performance of Scrum. In the following section, we analyze Scrum practices from social factor theories (social .
