IMPORTANT ALCOHOLS Methanol (wood alcohol): CH 3 OH Production: Useful as a solvent and industrial starting material Highly toxic, if taken internally causes blindness and/or death

IMPORTANT ALCOHOLS (continued) Ethanol (ethyl alcohol, grain alcohol): CH 3 CH 2 OH Produced commercially from ethylene and through biological (yeast) fermentation of carbohydrates Useful as a solvent, industrial starting material, fuel (gasohol), and found in alcoholic beverages Moderately toxic

ETHANOL PRODUCTION METHODS Hydration of ethylene: Yeast fermentation of carbohydrates:

IMPORTANT ALCOHOLS (continued) 2-Propanol (isopropyl alcohol) is the main component of rubbing alcohol. 1,2,3-Propanetriol (glycerol) is used as a food moistening agent (nontoxic) and for its soothing qualities (soaps).

IMPORTANT ALCOHOLS (continued) Antifreezes 1,2-ethanediol (ethylene glycol) 1,2-propanediol (propylene glycol)

EXAMPLES OF ALCOHOLS

PHENOLS Phenol behaves as a weak acid in water. Phenol can react with bases to form salt.

USES OF PHENOLS In a dilute solution, phenol is used as a disinfectant. Phenol derivatives used as disinfectants:

USES OF PHENOLS (continued) Phenol derivatives used as antioxidants in food:

NAMING ETHERS IUPAC name: Name the smaller of the two R groups as an alkoxy group attached to the parent chain by replacing the –yl ending of the R group with –oxy. Common name: Name the groups attached to the oxygen alphabetically and add the word ether. common: sec-butyl ethyl ether

CYCLIC ETHERS Heterocyclic rings contain atoms other than carbon in the ring.

PROPERTIES OF ETHERS Much less polar than alcohols More soluble in water than alkanes, but less soluble than alcohols Low boiling and melting points because of the inability to hydrogen bond between molecules Inert and do not react with most reagents (like alkanes) Highly flammable (like alkanes)

PROPERTIES OF ETHERS (continued) Hydrogen bonding of dimethyl ether: (a) with water and (b) no hydrogen bonding in the pure state.

THIOLS: THE –SH (SULFHYDRYL) GROUP Most distinguishing characteristic is their strong and offensive odor ethanethiol – added to natural gas 1-propanethiol – odor in garlic and onions trans-2-butene-1-thiol – odor associated with skunks

THIOL REACTIONS Oxidation forms disulfide (-S-S-) linkages, which are important structural features of some proteins: Specific example:

THIOL REACTIONS (continued) Oxidation reactions can be reversed with a reducing agent (H):

THIOL REACTIONS (continued) Reacts with heavy metals (Pb 2+, Hg 2+ ) to form insoluble compounds, with adverse biological results:

POLYFUNCTIONAL COMPOUNDS Polyfunctional compounds are compounds with two or more functional groups. Functional groups determine chemical properties of compounds. Example:

POLYFUNCTIONAL COMPOUNDS (continued)