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

IMPORTANT ALCOHOLS• Methanol (wood alcohol): CH3OH

• 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): CH3CH2OH

• 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)

• Antifreezes1,2-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 (Pb2+, Hg2+) 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)