Chapter 13 Alcohols, Phenols, Thiols, and Ethers Lecture Presentation Chapter 13 Alcohols, Phenols, Thiols, and Ethers Karen C. Timberlake

Chapter 13 Alcohols, Phenols, Thiols, and Ethers Anesthesia is typically administered by a nurse anesthetist who provides care before, during, and after a medical procedure. A nurse anesthetist gives medications to keep a patient asleep and pain-free while monitoring the patient’s vital signs.

Chapter 13 Readiness Core Chemistry Skills Naming and Drawing Alkanes (12.2)

13.1 Alcohols, Phenols, Thiols, and Ethers Functional groups such as an alcohol contain a hydroxyl group (— OH). a phenol contain a hydroxyl group (— OH) bonded to a benzene ring. a thiol contain an — SH group. CH3—CH2—SH Learning Goal Give the IUPAC and common names for alcohols, phenols, and thiols; draw their condensed and line-angle structural formulas.

Alcohols, Phenols, and Thiols Core Chemistry Skill Identifying Alcohols, Phenols, and Thiols

Naming Alcohols In the IUPAC system, replace the e with ol. With common names, use the name of the alkyl group followed by alcohol. Core Chemistry Skill Naming Alcohols and Phenols

Naming Alcohols For alcohols with three or more carbon atoms, number the carbons in the chain to give the position of the — OH group and any substituents on the chain. An alcohol with two — OH groups is named as a diol. An alcohol with three — OH groups is named as a triol.

Naming Cyclic Alcohols A cyclic alcohol is named as a cycloalkanol. If there are substituents, the ring is numbered from carbon 1, which is the carbon attached to the — OH group. Compounds with no substituents on the ring do not require a number for the hydroxyl group.

Naming Phenols The term phenol is the IUPAC name when a hydroxyl group (— OH) is bonded to a benzene ring. When there is a second substituent, the benzene ring is numbered starting with carbon 1, bonded to the — OH 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.

Guide to Naming Alcohols

Study Check Give the IUPAC name for the following compound:

Solution Give the IUPAC name for the following compound: ANALYZE Given Need THE alcohol, six-carbon IUPAC name PROBLEM chain, methyl substituent

Naming of Alcohols Give the IUPAC name for the following compound: STEP 1 Name the longest carbon chain attached to the — OH group by replacing the e in the corresponding alkane name with ol.

Solution Give the IUPAC name for the following compound: STEP 2 Number the chain starting at the end nearer to the — OH group. 2-hexanol 6 5 4 3 2 1

Solution Give the IUPAC name for the following compound: STEP 3 Give the location and name for each substituent relative to the — OH group. 5-methyl-2-hexanol 6 5 4 3 2 1

Study Check Give the IUPAC name for the following compound: A. B.

Solution Give the IUPAC name for the following compound: A. ANALYZE Given Need THE alcohol, five-carbon chain IUPAC name PROBLEM methyl substituent

Solution Give the IUPAC name for the following compound: B. ANALYZE Given Need THE phenol, IUPAC and PROBLEM bromo substituent common name

Solution STEP 1 Name the longest carbon chain attached to the — OH group by replacing the e in the corresponding alkane name with ol. Name an aromatic alcohol as a phenol. A. pentanol B. phenol

Solution STEP 2 Number the chain starting at the end closer to the — OH. The compound is a phenol because it consists of an — OH group attached to a benzene ring. A. 2-pentanol B. phenol 5 4 3 2 1 2 3 1

Solution STEP 3 Give the location and name for each substituent relative to the — OH group. A. 4-methyl-2-pentanol B. 3-bromophenol 5 4 3 2 1 2 3 1

Chemistry Link to Health: Alcohols and Phenols Methanol (methyl alcohol), the simplest alcohol, is found in many solvents and paint removers. 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. C6H12O6  2CH3—CH2—OH + 2CO2 is used as a solvent for perfumes, varnishes, and some medicines, such as tincture of iodine. Fermentation

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 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 (— SH) group. often have strong and sometimes disagreeable odors. are found in cheese, onions, garlic, and oysters. are used to detect gas leaks.

Naming Thiols Thiols, also known as mercaptans, are a family of sulfur-containing organic compounds that have a thiol group (— SH). In the IUPAC system, thiols are named by adding thiol to the alkane name of the longest carbon chain and numbering the carbon chain from the end nearer the — SH group. Thiols are sulfur-containing compounds and often have strong odors.

Thiols 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.