Transcript polyfunctional compounds - Clayton State University

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)
• 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 (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)