1. 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

2. Alcohols, Phenols, and Thiols

3. 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

4. Cyclic Alcohols
A cyclic alcohol is named as a cycloalkanol.

5. 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

6. 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.

7. 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.

8. 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.

9. 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.

10. Chemistry Link to Health: Alcohols and Phenols

11. 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.

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

13. 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.

14. 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.

15. 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.

16. 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.

17. 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.

18. 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.

19. 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.

20. 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.

21. 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.

22. 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

23. 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.

24. 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.

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

26. 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.

27. 13.4 Reactions of Alcohols and Thiols
A flaming dessert is prepared using heat from the combustion of an alcohol.

28. 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.

29. 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.

30. 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.

31. 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.

32. 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.

33. 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