ADIGUN LATIFAT 090224003 DEMEHIN ORE – OFE 090224008 FASUYI ABIMBOLA 090224010

1. NAME MATRIC NUMBER ADIGUN LATIFAT 090224003 DEMEHIN ORE – OFE 090224008 FASUYI ABIMBOLA 090224010 ADEGUNSOYE ADEFEMI 090224026 CHEMISTRY OF ALKANOIC ACID

2. ALKANOIC ACIDS Alkanoic acids, also know as organic carboxylic acids, contain the cabocyl group, -COOH as their functional group The most common of these are the aliphatic monocaboxylic acids which contain one carboxyl group per molecule, they form a homologous series with general formular of CnH2n+COOH where n >O. they are sometimes called fatty acids because some of them are found in natural fats and oils. The IUPAC name of each homologue is obtained by changing the ending of the corresponding alkane to –oic acid. Dicarboxylic acids have 2 carboxyl group per molecule e.g. ethanoic acid (oxalic acid) Cis –butenedioic acid (maleic acid) 2,3 dibydroxybutanedioic acid (tartaric acid) While tricarboxylic aid have 3 carboxylic acid per molecule e.g 2-hydroxypropane – 1,2,3 – tricarboxylic acid(citric acid) Two important aromatic carboxylic acids are Benzoic acid and 2 – hydroxybenzoic acid (salicylic acid)

3. Structure of a carboxylic acid Carboxylate ion The 3D structure of the carboxyl group

4. Naming of carboxylic(alkanoic acids) Number the longest carbon chain starting with the carbon atom of the COOH functional group. Name the carbon chain. Add the suffix -oic acid Nomenclature and examples Carboxylic acids are commonly named as indicated in the table below. Although rarely used, IUPAC-recommended names also exist. For example, butyric acid (C3H7CO2H) is, according to IUPAC guidelines, also known as butanoic acid.[9] The carboxylate anion R-COO– is usually named with the suffix -ate, so acetic acid, for example, becomes acetate ion. In IUPAC nomenclature, carboxylic acids have an -oic acid suffix (e.g., octadecanoic acid). In common nomenclature, the suffix is usually -ic acid (e.g., stearic acid). Straight-chained, saturated carboxylic acids

5. Carbon atomsCommon nameIUPAC nameChemical formulaCommon location or use 1 Formic acidMethanoic acidHCOOHInsect stings 2Acetic acidEthanoic acidCH3COOHVinegar 3 Propionic acidPropanoic acidCH3CH2COOHPreservative for stored grains 4Butyric acidButanoic acidCH3(CH2)2COOHRancid butter 5Valeric acidPentanoic acidCH3(CH2)3COOHValerian 6Caproic acidHexanoic acidCH3(CH2)4COOHGoat fat 7Enanthic acidHeptanoic acidCH3(CH2)5COOH 8Caprylic acidOctanoic acidCH3(CH2)6COOHCoconuts and breast milk 9Pelargonic acidNonanoic acidCH3(CH2)7COOHPelargonium 10Capric acidDecanoic acidCH3(CH2)8COOH 11Undecylic acidUndecanoic acidCH3(CH2)9COOH 12Lauric acidDodecanoic acidCH3(CH2)10COOH Coconut oil and hand wash soaps. 13Tridecylic acidTridecanoic acidCH3(CH2)11COOH 14Myristic acidTetradecanoic acidCH3(CH2)12COOHNutmeg

6. Carbon atoms Common name IUPAC name Chemical formula Common location or use 15PentadecanoicacidCH3(CH2)13COOH 16Palmitic acidHexadecanoic acidCH3(CH2)14COOHPalm oil 17 Margaric acidHeptadecanoic acid CH3(CH2)15COOH 18Stearic acidOctadecanoicacidCH3(CH2)16COOHChocolate, waxes, soaps, and oils 20 Arachidic acidIcosanoicacidCH3(CH2)18COOHPeanut oil

7. Examples of Carboxylic (Alkanoic) Acids

9. Properties They are very polar molecule. They form hydrogen bonds which results in their existence as dimmers. They have high boiling points due to the presence of hydrogen bonds. Their boiling point is higher than that of their corresponding alcohol. The 1st 4 members are miscible with water while the rest are not but miscible in organic solvents. They are soluble in bases forming salts.

10. Chemical Properties Ethanoic acid is a fairly stable compound which is not easily decomposed by heat. It is also unaffected by all ordinary reducing agents, oxidizing agents and dehydrating agents.

11. Acid Properties As a weak monobasic acid, ethanoic acids shows all the usual acidic properties, this it Neutralizes bases or alkalis to form salts, known as ethanoates, and water only. Attacks strongly electropositive metals e.g. magnesium and calcium. CH3COOH(aq)+NaOH(aq) CH3COONa(aq)+H2O 2CH3COOH(aq)+Mg(s) (CH3COO)2Mg(aq)+H2(g)

12. Ester Formation Ethanoic acid reacts reversibly with alkanols to form esters. For example, it reacts with ethanol when heated to produce ethyl ethanoate, CH3COOC2H5. The reaction is catalyzed by tetraoxosulphate(vi)acid. CH3COOH(aq) +C2H5(aq) CH3COOC2H5(L)+ H2O(L) Ethanoicacid alkanol ester(ethylethanoates) water A carboxylate ester. R and R' denote any alkyl or aryl group Esters are usually derived from an inorganic acid or organic acid in which at least one -OH (hydroxyl) group is replaced by an -O-alkyl (alkoxy) group, and most commonly from carboxylic acids and alcohols. That is, esters are formed by condensing an acid with an alcohol. Esters are ubiquitous. Most naturally occurring fats and oils are the fatty acid esters of glycerol. Esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important with plastics,with monomers linked by ester moieties

13. Esterification Reactions Esters are produced in a condensation reaction between a carboxylic (alkanoic) acid and an alkanol (alcohol). This is known as an esterification reaction. carboxylic (alkanoic) acid + alkanol (alcohol) ester + water eg,     2CH3COOH + CH3OH CH3COOCH3 + H2O ethanoic acid + methanol methyl ethanoate + water

14. Uses • Ethyl acetate for manufacture of nail polish remover, modelpaint, model airplaneglue. Ethyl formate for the production of rum.Odor • Carboxylic acids often have strong odors, especially the volatile derivatives. Most common are acetic acid (vinegar) and butanoic acid (rancid butter). On the other hand, esters of carboxylic acids tend to have pleasant odors and many are used in perfumes. Carboxylic acids are used in the production of polymers, pharmaceuticals, solvents, and food additives. Industrially important carboxylic acids include acetic acid (component of vinegar, precursor to solvents and coatings), acrylic and methacrylic acids (precursors to polymers, adhesives), adipic acid (polymers), citric acid (beverages), ethylenediaminetetraacetic acid (chelating agent), fatty acids (coatings), maleic acid (polymers), propionic acid (food preservative), terephthalic acid (polymers)

15. Chlorination Formation of acyl chloride:- glacial or anhydrous ethanoicacid reacts with phosphorus(v) chloride in the cold to form ethanoyl chloride, CH3COCL, a colourless liquid which fumes in air. Formation of chloroalkanoic acid. If chlorine is passed into boiling ethanoic acid, in the presence of sunlight, iodine or red phosphorus as the catalyst, substitution will take place in the methyl group (-CH3 ) while the carcoxyl group (-COOH) remains intact. The product of this reaction is monochloroethanoic acid, CH2CLCOOH. If the reaction is prolonged, further chlorination will occur to produce the Dichloroethanoic acid, CHCl2COOH, and Trichloroethanoic acid, CCl3COOH, Successively Bromine reacts with ethanoic acid in a similar way as chlorine, though less readily.

16. Decarboxylation reaction If sodium ethanoate is heated strongly with soda-lime methane will be produced together with carbon (iv) oxide CH3COONa(aq)CH4(g)+CO2(g)

17. Reduction Alkanoicacids can be reduced to primary alkanols, using litiumtetrahydridoaluminate, LiAlH4, as reducing agent to supply the hydrogen. CH3COOH(aq)+4[H] CH3CH2OH(l)+H2O(l)

18. Uses Ethanoic acid is used is making compounds like i. Ethenylethanoate (vinyl acetate) which is used in vinyl resins ii. Ethanoic anhydride which is used in asipirin; iii. Cellulose ethanoate (cellulose acetate) which is used for packing in varnishes, in the filter tips of cigarettes as well as in the manufacture of synthetic fibres like rayon and artificial silk; iv. Propanone(acetones) and v. Various dyes vi. Ethanoicacid is also an important organic solvent. It is used in the food industry as vinegar, for preserving and flavouring food. Sometimes, it is also used for coagulating rubber latex.