Alcohol aldehydes cetones and carboxylic acids

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1 Alcohol aldehydes cetones and carboxylic acids 1

2 Classes of organic compounds 2

3 Alcohols Alcohols are organic compounds containing hydroxyl (-OH) group attached to C atom. In an alcohol, -OH group replaces a hydrogen atom in an alkane. In a phenol, -OH group is attached to a benzene ring. Methane 3

4 Classification of alcohols (1) 4

5 Classification of alcohols (2) According to the number of -OH groups, there are monohydroxylic, dihydroxylic and trihydroxylic alcohols. H 3 C CH 2 OH H 2 C CH 2 OH OH ethanol (monohydroxylic alcohol) According to the saturation of C atom chain, alcohols fall into saturated and unsaturated aliphatic, cyclic and aromatic. H 3 C CH 2 CH 2 OH 1,2-ethanediol (dihydroxylic alcohol) H 2 C CH CH 2 OH OH OH 1,2,3-propanetriol (trihydroxylic alcohol) glycerol OH CH 2 OH 1-propanol (aliphatic alcohol) cyclohexanol (cyclic alcohol) phenylmethanol (aromatic alcohol) 5

6 Naming alcohols (1) 6

7 Naming alcohols (2) Dihydroxylic alcohols are called glycols, or according to IUPAC: -diols; trihydroxylic alcohols: -triols. 7

8 Chemical properties of alcohols (1) Acidic-basic properties: although OH group is polar, alcohols are very weak acids. The acidic properties of di- and trihydroxylic alcohols are stronger than those of monohydroxylic alcohols. They react with bases producing salts: diols form glycolates, triols - glycerates. The reaction for identification of -CHOH-CHOHfragment in various compounds: CH 2 CH 2 OH H O + Cu(OH) 2 + Cu O 2 C 2KOH C O O OH blue colour precipitate H 2 CH 2 CH 2 2- water soluble blue complex compound 2K + + 4H 2 O 8

9 Chemical properties of alcohols (2) Oxidation of primary alcohols results in formation of aldehydes, and then aldehydes undergo further oxidation to carboxylic acids. R CH 2 OH [O] -H 2 O Under oxidation of secondary alcohols, ketones are produced. Ketones are more resistant to oxidation. R CH R1 OH R C O H [O] [O] -H 2 O R C R1 O R C O OH 9

10 Chemical properties of alcohols (3) Formation of ethers: R1 CH 2 OH +R2 CH 2 OH R1 CH 2 O CH 2 R2 Formation of esters with both mineral and organic acids. R1 CH 2 OH + H 2 SO 4 R1 CH 2 O SO - 3 O R1 CH 2 OH + R COOH R C O CH 2 R1 Esters of glycerol and organic acids are triacylglycerols (fats). 10

11 Ethers 11

12 Physical properties of alcohols 12

13 Aromatic alcohols 13

14 Oxidation of aromatic alcohols 14

15 Phenols(1) Phenol is soluble in water because the hydroxyl group ionizes slightly as a weak acid. 15

16 Phenols(2) Phenol 1,2,5-benzenetriol 16

17 Chemical properties of phenols (1) Phenols are are stronger acids than aliphatic and aromatic alcohols. Form salts: OH NaOH -H 2 O ONa Form ethers: O CH 3 phenol sodium phenolate OCOCH 3 Form esters: methyl phenyl ether (anisol) phenylethanoate 17

18 Chemical properties of phenols (2) Phenols are characterized with one specific reaction. They can form coloured compounds reacting with ferric trichloride. In such reaction phenols form coloured coordination compounds - ferric phenolates: FeCl 3 + 6C 6 H 5 OH = [Fe(OC 6 H 5 ) 6 ] H + + 3Cl - 18

19 Phenols: examples HO Physiologically active aromatic alcohols: OH OH CH CH 2 NH CH 3 HO CH CH 2 NH 2 HO adrenaline HO noradrenaline 19

20 Alcohol in the body 20

21 Carbonyl compounds: Aldehydes and ketones 21

22 The polar carbonyl group 22

23 Groups of carbonyl compounds Aldehydes ethanal benzaldehyde Ketones propanone (acetone) Benzophenone 23

24 Naming aldehydes 24

25 Naming ketones 25

26 Physical properties of carbonyl compounds (1) Aldehydes and ketones with up to 4 C atoms in molecules are volatile liquids of specific odour. They are soluble in water and in organic solvents. Solubility in water decreases with an increase of a number of C atoms in a chain. Aldehydes containing 8-10 C atoms in a chain have odour of flowers and are used in perfumery. 26

27 Physical properties of carbonyl compounds (2) 27

28 Chemical properties of carbonyl compounds Reduction producing alcohols (both aldehydes and ketones). H H 3 C C CH 3 O propanone (acetone) H 3 C C CH 3 OH Oxidation producing acids (only aldehydes). O H 3 C C H Acetaldehyde [O] O H 3 C C OH Acetic acid 28

29 Tollens test Ag + + 1e - Ag (s) Example: O H 3 C C H + 2Ag + [O] Acetaldehyde Tollens reagent 2Ag(s) + Silver mirror O H 3 C C OH Acetic acid 29

30 Benedict s test OH O Example: H 3 C C C H 2-Hydroxypropanal + Cu 2+ Cu 2 O(s) + C Benedict's reagent Brick-red solid OH O H 3 C C OH 2-Hydroxypropanoic acid 30

31 Carboxylic acids 31

32 Preparation of carboxylic acids 32

33 Naturally occurring carboxylic acids 33

34 Naming carboxylic acids 34

35 Some common names of carboxylic acids Common IUPAC Formula Formic methanoic HCOOH Acetic ethanoic CH 3 COOH Propionic propanoic CH 3 CH 2 COOH Butyric butanoic CH 3 (CH 2 ) 2 COOH Capric decanoic CH 3 (CH 2 ) 8 COOH Lauric dodecanoic CH 3 (CH 2 ) 10 COOH Stearic octadecanoic CH 3 (CH 2 ) 16 COOH 35

36 Aromatic carboxylic acids 36

37 Polar functional groups in carboxylic acids Carboxylic acids are among the most polar organic compounds because the functional carboxyl group consists of two polar groups: a hydroxyl (-OH) group and a carbonyl (C=O) group. O + H C O H

38 Physical properties of carboxylic acids 38

39 The acidity of carboxylic acids The equilibrium concentrations of the carboxylic acid R-COOH and the carboxylate ion R-COO - depend upon ph: At low ph the acid form predominates, at ph 7.4 the carboxylate ion predominates. Carboxylic acids react with bases to produce carboxylate salts and water. 39

40 Salts of carboxylic acids The carboxylic acid salts are solids at room temperature. Because they are ionic compounds, carboxylic acid salts of the alkali metals (Li +, Na +, and K + ) and NH 4 + are usually soluble in water. 40

41 Soap formation 41

42 Cleaning action of soap One of the problems of using soaps is that the carboxylate end reacts with ions in water such as Ca 2+ and Mg 2+ and forms insoluble substances. 2CH 3 (CH 2 ) 16 COO - + Mg 2+ [CH 3 (CH 2 ) 16 COO - ] 2 Mg 2+ Stearate ion Magnesium stearate (insoluble) 42

43 Esterification Carboxylic acids, acid chlorides and acid anhydrides react with alcohols to produce esters. Esters can also be formed when inorganic acids (e.g., phosphoric acid) react with alcohols. 43

44 Esters 44

45 Examples of esters 45

46 Reactions of esters - hydrolysis 46

47 Esters in medicine 47

48 Acid anhydrides They form from the combination of two carboxylic acids and the loss of water. 2 O H 3 C C OH ethanoic acid H +, heat O O H 3 C C O C CH 3 ethanoic anhydride + H 2 O Examples: O O H 3 C CH 2 C O C CH 2 CH 3 propanoic anhydride O O C O C benzoic anhydride 48

49 Reactions of acid anhydrides 49

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