13.1 Alcohols, Phenols, Thiols, and Ethers Functional groups such as an alcohol contain a hydroxyl group a phenol contain a hydroxyl group bonded to a benzene ring. a thiol contain an

Alcohols, Phenols, and Thiols

Naming Alcohols (1 of 2) In the I U P A C system, replace the e with o l. With common names, use the name of the alkyl group followed by alcohol. Formula IUPAC Common Name C H4 methane blank C H3—O H Methanol Methyl alcohol C H3—C H3 Ethane C H3—C H2—O H Ethanol Ethyl alcohol

Cyclic Alcohols A cyclic alcohol is named as a cycloalkanol.

Phenols The term phenol is the I U P A C name when a hydroxyl group The terms ortho, meta, and para are used for the common names of simple phenols. The common name cresol is also used for methylphenols

Chemistry Link to Health: Alcohols and Phenols Methanol (methyl alcohol), the simplest alcohol, is found in many solvents and paint removers. Methanol is produced when cellulose (wood products) are fermented and distilled is oxidized to formaldehyde when ingested and can cause headaches, blindness, and death.

Chemistry Link to Health: Alcohols and Phenols Ethanol (ethyl alcohol) has been known since prehistoric times as an intoxicating product. is formed by the fermentation of grains, sugars, and starches. is used as a solvent for perfumes, varnishes, and some medicines, such as tincture of iodine.

Chemistry Link to Health: Alcohols and Phenols 1,2-ethanediol (ethylene glycol) is used as an antifreeze in heating and cooling systems. is also a solvent for paints, inks, and plastics. is used in the production of synthetic fibers such as Dacron. If ingested, it is extremely toxic. In the body, it is oxidized to oxalic acid, which forms insoluble salts in the kidneys that cause renal damage, convulsions, and death.

Chemistry Link to Health: Alcohols and Phenols “BPA FREE” Bisphenol A (BPA) is used to make polycarbonate, a clear plastic that is used to manufacture beverage bottles, including baby bottles. Washing polycarbonate bottles with certain detergents or at high temperatures disrupts the polymer, causing small amounts of BPA to leach from the bottles.

Chemistry Link to Health: Alcohols and Phenols

Thiols Thiols contain a thiol often have strong and sometimes disagreeable odors. are found in cheese, onions, garlic, and oysters. are used to detect gas leaks.

Thiols Thiols, aka mercaptans, are a family of sulfur- containing organic compounds that have a thiol group named by adding thiol to the alkane

Thiols (2 of 2) Methanethiol is the compound that has an odor characteristic of oysters, cheddar cheese, onions, and garlic. Garlic also contains 2-propene-1-thiol. The odor of onions is due to 1-propanethiol, which is also a lachrymator, a substance that makes eyes tear.

13.2 Ethers An ether consists of an oxygen atom that is attached by single bonds to two carbon groups that are alkyl or aromatic groups.

Ethers An ether contains an between two carbon groups that are alkyls or aromatic rings. has a common name that gives the alkyl names of the attached groups, followed by ether.

Chemistry Link to Health: Ethers as Anesthetics Anesthesia is the loss of sensation and consciousness. A general anesthetic is a substance that blocks signals to the awareness centers in the brain. gives the patient a loss of memory, a loss of feeling pain, and an artificial sleep. Forane (isoflurane) is an inhaled anesthetic.

Chemistry Link to Health: Ethers as Anesthetics Ether was used in anesthetics for hundreds of years until the 1950s, when new anesthetics were developed that retain the ether group. replace hydrogen atoms on the carbon with halogen atoms to reduce the volatility and flammability of the ethers.

Boiling Points Because there is a large electronegativity difference between the oxygen and hydrogen atoms in the Hydrogen bonds form between alcohol molecules but not between ether molecules.

Boiling Points Hydrogen bonds cannot form between ether molecules because there are not any polar Alcohols with similar mass have higher boiling points than do ethers because alcohols require higher temperatures (more energy) to break their hydrogen bonds. The boiling points of ethers are similar to those of alkanes because neither can form hydrogen bonds.

Solubility: Alcohols and Ethers contain polar — O H groups and form hydrogen bonds with other alcohol molecules and with water. that have one to three carbons are soluble in water. The solubility of alcohols in water decreases with increasing number of carbons.

Solubility: Alcohols and Ethers can form hydrogen bonds with water. form fewer hydrogen bonds than alcohols with water. are only slightly soluble in water when they have fewer than four carbon atoms. are not soluble in water if they have five or more carbon atoms.

Solubility: Phenols which makes it a weak acid Phenols, once used as antiseptics, are slightly soluble in water. have an that can form hydrogen bonds with water can react with water to produce phenoxide ions. In water, the of phenol ionizes slightly, which makes it a weak acid

Phenol and Antiseptics Antiseptics, substances applied to the skin to kill microorganisms that cause infection, were once made of dilute solutions of phenol. were once used to disinfect wounds to prevent post-surgical infections such as gangrene. are now used in Lysol, used to disinfect surfaces, and contain the antiseptics 2-phenylphenol and 2-benzyl-4-chlorophenol.

Chemistry Link to Health: Hand Sanitizers Hand sanitizers containing ethanol as their active ingredient kill most bacteria and viruses that spread colds and flu. are approximately 60% (v/v) but can be as high as 85% (v/v). are highly flammable and produce a transparent, blue flame. may also contain triclosan, which can accumulate in the environment, promoting growth of antibiotic-resistant bacteria.

Study Check (3 of 3) Indicate whether each of the following is soluble in water and explain why. A . B.

Solution Indicate whether each of the following is soluble in water and explain why. not soluble Alcohols with long carbon chains (nonpolar) are not soluble. soluble Short-chain alcohols form hydrogen bonds with water.

13.4 Reactions of Alcohols and Thiols A flaming dessert is prepared using heat from the combustion of an alcohol.

Oxidation and Reduction In organic chemistry, oxidation reactions increase the number of carbon–oxygen bonds by the addition of oxygen or a loss of hydrogen atoms. reduction reactions reduce the number of bonds between carbon and oxygen atoms.

Chemistry Link to Health: Methanol Poisoning Methanol is also known as methyl alcohol. highly toxic and found in windshield washer fluid, Sterno, and paint strippers. rapidly absorbed and oxidized to formaldehyde and then formic acid.

Oxidation of Thiols When thiols undergo oxidation, an H atom is lost from each of two the product is a disulfide. Protein in hair is cross-linked by disulfide bonds found in the amino acid cysteine.

Chemistry Link to Health: Oxidation of Alcohol in the Body Ethanol acts as a depressant and kills or disables more people than does any other drug. consumption can be analyzed by using a breathalyzer. is metabolized by a social drinker at a rate of 12–15 mg/dL per hour. is metabolized by an alcoholic at a rate of 30 mg/dL per hour.

Chemistry Link to Health: Oxidation of Alcohol in the Body The acetaldehyde produced from ethanol in the liver is further oxidized to acetic acid, which is converted to carbon dioxide and water in the citric acid cycle. Liver enzymes can eventually break down ethanol, but the aldehyde and carboxylic acid intermediates can cause considerable damage to liver cells.

Chemistry Link to Health: Oxidation of Alcohol in the Body Table 13.2 Typical Behaviors Exhibited by a 150-lb Person Consuming Alcohol Number of Beers (12 oz) or Glasses of Wine (5 oz) in 1 h Blood Alcohol Level (% m/v) Typical Behavior 1 0.025 Slightly dizzy, talkative 2 0.050 Euphoria, loud talking and laughing 4 0.10 Loss of inhibition, loss of coordination, drowsiness, legally intoxicated in most states 8 0.20 Intoxicated, quick to anger, exaggerated emotions 12 0.30 Unconscious 16–20 0.40–0.50 Coma and death