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ALCOHOLS, PHENOLS and ETHERS R-OH Functional group of an alcohol molecule C2H5OH ethanol ethyl alcohol propan-2-ol, 2-propanol, iso, isopro, isoprop, C3H7OH rubbing alcohol, or the abbreviation IPA – isopropyl alcohol) Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Menthol is a major component of mint. cholesterol The best source is probably Mentha arvensis, Corn Mint, whose oil is up to 85% (-)-menthol. High-density lipoprotein (HDL) Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Glycerin, glycerine, propane-1,2,3-triol Bombykol The sex pheromone of the silk moth A fatty alcohol with two double bonds, bombykol (tr-10,cis-12-hexadecadien-1-ol), was also shown to be excreted as a very strong attractive substance by the female of silk-worm (Bombyx mori). The bombyx mori silk moth Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS water water water H O H H O H H O H phenol alcohol R O H O H phenol group OH H3C C H2 H2 C OH propan-1-ol Chemistry 21A -OH ether group ether R O R O diethyl ether (ether) hydroxyl group R~ alkyl group O diphenyl ether Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Nomenclature of Alcohols 1. Alcohols are named by finding the longest continues carbon chain and changing the ending to –ol (e.g., methanol, ethanol, propanol, etc.). 2. With unsaturated alcohols, two endings are needed, one for the double or triple bond and one for the hydroxyl group. The –ol suffix is last and takes precedence in the numbering. 3. If the hydroxyl group is directly attached to an aromatic ring, the compound is named as a phenol. 4. If the hydroxyl group occurs in a carboxylic acid, aldehyde, or ketone, it is named as a substituent (hydroxy) because the former functionalities have higher priority. 5. The common names for the alcohols are the alkane chain named as a substituent followed by the word alcohol (e.g., methyl alcohol, ethyl alcohol, etc.) H3C OH methanol methyl alcohol H3C H2 C OH ethanol ethyl alcohol Chemistry 21A H3C H2 C OH C H2 OH propan-1-ol, 1-propanol, C H3C H CH3 propan-2-ol, 2-propanol, Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS C4H9OH alcohols H2 C H3C C H2 H2 C CH3 OH OH CH3 C H3C H C H2 CH3 C OH H3C H C H2 H3C C OH CH3 1-butanol 2-butanol 2-methyl-1-propanol 2-methyl-2-propanol n-butyl alcohol sec-butyl alcohol isobutyl alcohol tert-butyl alcohol OH HO HO H2 C C H2 OH H2 H2 C H C OH C HO OH OH ethanediol ethylene glycol OH HO trans-3-methylcyclohexanol H3C OH OH 1,2,3-propanetriol glycerin Chemistry 21A 1-methylcyclopentanol Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS OH OH 3-methylphenol phenol OH HO 4-ethylphenol OH Cl Cl alcohol Cl 2,4,6-trichlorophenol Chemistry 21A benzyl alcohol Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS H2 C H3C C H2 H2 C CH3 OH OH CH3 C OH H3C H C H2 CH3 C H3C H C H2 H3C C OH CH3 1-butanol 2-butanol 2-methyl-1-propanol 2-methyl-2-propanol n-butyl alcohol sec-butyl alcohol isobutyl alcohol tert-butyl alcohol primary alcohol tertiary alcohol primary alcohol HO HO H2 C C H2 secondary alcohol OH OH H3C OH OH ethanediol ethylene glycol trans-3-methylcyclohexanol Chemistry 21A 1-methylcyclopentanol Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Water has an unusually high boiling point because of the hydrogen bonds between the H2O molecules. Alcohols can form similar hydrogen bonds. As a result, alcohols have boiling points that are much higher than alkanes with similar molecular weights. The boiling point of ethanol, for example, is 78.5ºC, whereas propane, with about the same molecular weight, boils at -42.1ºC. The difference in boiling points between alkanes and alcohols with the same number of carbon atoms decreases when the total number of carbons increases (i.e. with the increase of hydrophobic character of alcohols). CH3CH2OCH2CH3 CH3CH2CH2CH2OH BP = 34.5ºC BP = 117.2ºC d = 0.7138 g/mL d = 0.8098 g/mL insoluble in water soluble in water Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Solubilities of Alcohols in Water Solubility in Formula Name Water (g/100 g) CH3OH CH3CH2OH CH3(CH2)2OH OH OH methanol infinitely soluble ethanol infinitely soluble OH propanol infinitely soluble CH3(CH2)3OH butanol 9 CH3(CH2)4OH pentanol 2.7 CH3(CH2)5OH hexanol 0.6 CH3(CH2)6OH heptanol 0.18 CH3(CH2)7OH octanol 0.054 CH3(CH2)9OH decanol insoluble in water Chemistry 21A OH hydrophilic part of the molecule OH hydrophobic part of the molecule OH Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS As the length of the alcohol increases, the effect of hydrogen bonding decreases and hydrophobic forces become dominant. The difference in boiling points between alkanes and alcohols with thw same number of carbon atoms decreases when the total number of carbons increases (i.e. with the increase of hydrophobic character of alcohols). Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS dehydration reaction synthesis of ethers H3C H2 C C H2 OH + HO Chemistry 21A C H2 H2 C H2SO4 CH3 H3C H2 C C H2 O C H2 H2 C CH3 Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS H3C C H2 oxydation oxydation H ethanol acetaldehyde Chemistry 21A H3C O H3C OH O OH acetic acid Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS H3C H CH3 C secondary alcohol oxydation CH3 H3C O OH isopropyl alcohol (2-propanol) dimethyl ketone (acetone) R R' OH R" tertiary alcohol no reaction oxydation CH3 H3C OH oxydation no reaction CH3 Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS C2H5OH ethanol ethyl alcohol Made from corn and other crops (fermentation) yeast C6H12O6 → C2H5OH + O2 Pure 100% ethanol has an octane rating of 113. Adding 10% ethanol to gasoline raises the overall octane by 2 to 3 points. Lower BTU value than gasoline 2C2H5OH + 2CO2 → CH3COOH + H2O H2C CH2 ethylene (ethene) 70 atm 300oC H3C C H2 OH For most of human history, acetic acid, in the form of vinegar, has been made by acetic acid bacteria of the genus Acetobacter. Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS heat, pressure, catalyst CO + 2H2 CH3OH CH3OH → H2C=O → HCOOH methanol formaldehyde formic acid Aqueous solution of formaldehyde is called formalin used for storing specimens and cadavers. Methanol is produced naturally in the anaerobic metabolism of many varieties of bacteria common laboratory solvent traditional denaturant for ethanol, thus giving the term methylated spirit About 40% of methanol is converted to formaldehyde, and from there into products as diverse as plastics, plywood, paints, explosives, and permanent press textiles. Drag racers and mud racers also use methanol as their primary fuel source. Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS propan-2-ol, 2-propanol, iso, isopro, isoprop, C3H7OH rubbing alcohol, or the abbreviation IPA – isopropyl alcohol) Ethylene glycol Monoethylene glycol MEG 1,2-ethanediol widely used as an automotive antifreeze odorless, colorless, syrupy, sweet tasting, toxic liquid propylene glycol, 1,2-propanediol, 1,2-Dihydroxypropane, methyl ethyl glycol (MEG), methylethylene glycol, PG, Sirlene, Dowfrost moisturizer in medicines,cosmetics, food, toothpaste, mouth wash, and tobacco products Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Glycerin, glycerine, propane-1,2,3-triol In foods and beverages, glycerol serves as a humectants, solvent and sweetener, and may help preserve foods. It is also used as filler in commercially prepared low-fat foods (e.g., cookies), and as a thickening agent in liqueurs. Glycerol also serves as a way, along with water, to preserve certain types of leaves. Glycerol is also used as a sugar substitute. In this regard, it has approximately 27 calories per teaspoon and is 60% as sweet as sucrose. Although it has about the same food energy as table sugar, it does not raise blood sugar levels, nor does it feed the bacteria that form plaques and cause dental cavities. As a food additive, glycerol is also known as E number E422. Example of an unsaturated fat triglyceride. Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS CH4 < NH3 < HCCH < ROH < H2O < phenols < H2CO3 < RCOOH < HF ONa OH + NaOH SB SA water insoluble + H2O WB WA water soluble OH + NaHCO3 Chemistry 21A NR phenol < H2CO3 Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Joseph Lister, 1st Baron Lister, (1827 – 1912) was an English surgeon who promoted the idea of sterile surgery while working at the Glasgow Royal Infirmary. He successfully introduced carbolic acid (phenol) to sterilize surgical instruments and to clean wounds, which led to reduced post-operative infections and made surgery safer for patients. 2-Phenylphenol, or ortho-phenylphenol, is an ingredient in Lysol, and is an agricultural fungicide. Chemistry 21A 2-Benzyl-4-chlorophenol is an ingredient in Lysol. Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS 4-Chloro-3,5-dimethylphenol, or chloroxylenol, is a nonirritating topical antiseptic used in a number of antibacterial soaps. 2,6-di-tert-butyl-4-methylphenol; 2,6-di-tert-butyl-p-cresol (DBPC); butylated hydroxytoluene; BHT Chemistry 21A Butylated hydroxytoluene (BHT), also known as butylhydroxytoluene, is a organic compound that is primarily used as an antioxidant food additive (E number E321) as well as in cosmetics, pharmaceuticals, jet fuels, rubber, petroleum products, and embalming fluid Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS 4-Hexylresorcinol is a chemical compound with anaesthetic, antiseptic and antihelmintic properties. It can be used topically on small skin infections, or as an ingredient in throat lozenges. Anthelmintics or antihelminthics are drugs that expel parasitic worms (helminths) from the body, by either stunning or killing them. They may also be called vermifuges (stunning) or vermicides (killing). 4-hexylbenzene-1,3-diol Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries. It is used in perfumery, in cosmetics, and as a food additive to impart a fruity odor. Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS PHENOLS are next-generation anti-oxidant found throughout nature in some of the healthiest foods. PHENOLS are the common health-giving link that ties together foods such as Red Wine, Green Tea, Dark Chocolate, and Super-Berries. Molecular structure of apigenin, a polyphenol antioxidant Chemistry 21A A polyphenol antioxidant is a type of antioxidant containing a polyphenolic substructure. In human health these compounds, numbering over 4000 distinct species, are thought to be instrumental in combating oxidative stress, a process associated with some neurodegenerative diseases and some cardiovascular diseases. Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS dimethyl ether, an aerosol spray propellant ether group ether R O R O diethyl ether (ether) A common low boiling solvent (b.p. 34.6°C), and an early anaesthetic. Polyethylene glycol has a low toxicity and is used in a variety of products. It is the basis of a number of laxatives (such as Movicol and polyethylene glycol 3350, or MiraLax or GlycoLax). Polyethylene glycol (PEG) It is the basis of many skin creams, as cetomacrogol, and sexual lubricants, Anisole (methoxybenzene) O diphenyl ether Chemistry 21A An aryl ether and a major constituent of the essential oil of anise seed. Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Physical Properties: The polar nature of the C-O bond (due to the electronegativity difference of the atoms ) results in intermolecular dipole-dipole interactions. An ether cannot form hydrogen bonds with other ether molecules since there is no H to be donated (no -OH group) Ethers can be involved in H-bonding with systems able to donate H (e.g. water). The implications of these effects are: lower melting and boiling points compared to analogous alcohols solubility in aqueous media similar to analogous alcohols. CH3CH2OCH2CH3 CH3CH2CH2CH2OH BP = 34.5ºC BP = 117.2ºC d = 0.7138 g/mL d = 0.8098 g/mL insoluble in water soluble in water Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Ethers can act as a hydrogen-bond acceptor, as shown in the figure below. But, they can't act as hydrogen-bond donors. As a result, ethers are less likely to be soluble in water than the alcohol with the same molecular weight. The absence of an -OH group in an ether also has important consequences for its chemical properties. Unlike alcohols, ethers are essentially inert to chemical reactions. They don't react with most oxidizing or reducing agents, and they are stable to most acids and bases, except at high temperatures. They are therefore frequently used as solvents for chemical reactions. However, ethers are generally extremely FLAMMABLE and tend, If exposed to air for longer periods of time, to form EXPLOSIVE PEROXIDES. Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS A thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom (-SH). Being the sulfur analogue of an alcohol group (-OH), this functional group is referred to either as a thiol group or a sulfhydryl group. More traditionally, thiols are often referred to as mercaptans. The preferred method (used by the IUPAC) is to add the suffix -thiol to the name of the alkane. The method is nearly identical to naming an alcohol. Example: CH3SH would be methanethiol. An older method, the word mercaptan replaces alcohol in the name of the equivalent alcohol compound. Example: CH3SH would be methyl mercaptan. (CH3OH would be methyl alcohol) Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Many thiols are colorless liquids having an odor resembling that of garlic. The odor of thiols is often strong and repulsive, particularly for those of low molecular weight Natural gas distributors began adding various forms of pungent thiols, originally ethanthiol, to natural gas, which is naturally odorless, after the deadly 1937 New London School explosion in New London, Texas. Most gas odorants utilized in the world contain mixtures H3C of mercaptans and sulfides, with t-butyl mercaptan as the main odor constituent. Cysteine Chemistry 21A (oxydation) CH3 SH CH3 Cystine, showing disulfide bond Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Diallyl disulfide (4,5-dithia-1,7-octadiene) is an organosulfur compound, along with diallyl trisulfide and diallyl tetrasulfide it is one of the principal components of the distilled oil of garlic. Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS 2R-SH + (O) → R-S-S-R + H2O 2CH3SH + (O) → CH3-S-S-CH3 thiol disulfide 2CH3SH + Pb2+ → CH3-S-Pb-S-CH3 + 2H+ Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Chemistry 21A Dr. Dragan Marinkovic ALCOHOLS, PHENOLS and ETHERS Chemistry 21A Dr. Dragan Marinkovic