Alcohols, Phenols, And Ethers

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ORGANIC CHEMISTRY.

Transcript of Alcohols, Phenols, And Ethers

  • Alcohols and Phenols

  • General Formulas and Functional GroupsTwo of the three families contain a hydroxyl group (OH)AlcoholsPhenolsEthersOften made from alcohols and phenols

    All are considered organic derivatives of water.

  • General Formulas

    Bent moleculeCentral oxygen atomHydrogen and alkyl group attached (R) or an aryl group (Ar)

  • General Formulas ContAlcoholsR-O-HPhenolsAr-OHBenzene ring with an OHEthersR-O-R

  • Classification and Nomenclature of AlcoholsProperties of alcohols depend on the arrangement of the carbon atoms of the moleculePrimary (1) carbon atom

  • Secondary (2) carbon atom

  • Tertiary (3) carbon atom

  • Classification and Nomenclature of AlcoholsPrimary AlcoholRCH2OHSecondary AlcoholR2CHOHTertiary AlcoholR3COH

  • IUPAC NamingName the longest continous chain of carbons containing the OH groupNumber which carbon the OH is attached toEnd name in olIf more than one hydroxyl group, use suffixes diol, -triol, etc.

  • Physical Properties of Alcohols Replacement of hydrogen with a hydroxyl group greatly changes propertiesNot as homologous as alkanesHigher boiling pointsDue to strong intermolecular attractionsSolubilityThe more compact the molecule is, the more soluble it is4-5 carbons or lesssoluble in water

  • Preparation of AlcoholsHydration Reactions

  • Markovnikovs RuleThe hydroxyl group goes on the carbon with fewer hydrogens

  • Production of alcoholsMethanol

    1.7 billion gallons produced a yearUsed in formaldehyde, acetic acid, fuels (MTBE), silicones, refrigerants

  • Production of AlcoholsEthanol Produced from sugars or starches by fermentation

    C6H10O5 C6H12O6 2CH3CH2OH + 2CO2(Enzymes as catalysts)

    Its the alcohol thats found in those certain beverages that people shouldnt drink

  • Production of Alcohols ContWines12% ethanolChampagnes14-20% ethanolBeers4% ethanolWhiskey50% ethanol

    Proof spirit: alcoholic content of a beverage, twice that of the alcohol content by volume (whiskey: 100 proof)

  • Physiological Effects of AlcoholsLD50 (Lethal dose to 50% of a population)Tested on animalsVaries per species though

  • MethanolCan cause permanent blindness or death in high amountsVapors are very dangerous as well

  • EthanolToxic to humansAcute poisoning kills several hundred a year (drinking contests)Long term poisioningMost serious drug problem in US40 times more addicts than heroin

  • Isopropyl AlcoholRubbing alcoholRapid evaporationAntisepticMore toxic than ethanol, but induces vomittingUsed for the manufacture of acetone

  • Chemical Properties of AlcoholsReactionsOccur on the functional groupsMay involve hydrogen atoms as well

    Dehydration Oxidation

  • DehydrationRemoval of waterSulfuric acid as a catalystProduces:Ether (excess ROH) + waterAlkene (excess H2SO4) + water

  • OxidationResult depends on if alcohol is primary, secondary, or tertiaryPrimaryProduces an aldehyde Then goes through further oxidation to produce a carboxylic acidSecondaryProduces a ketoneTertiaryNo reactionCant break the carbon-carbon bond

  • Oxidation Cont

  • Multifunctional Alcohols: Glycols and Glycerol

    More than one hydroxyl groupPolyhydric groups Dihydric alcoholsTrihydric alcohols

  • GlycolsDihydric alcohols1,2 ethanediol (ethylene glycol)HOCH2CH2OHTwo hydroxyl groupsextensive intermolecular hydrogen bondingHigher boiling pointUsed as anti-freeze

  • GlycerolMost important trihydric alcoholSyrupy liquidNontoxic, product of the hydrolysis of fats and oilsNitroglycerinDetonates on slight impactReaction produces temps of 3000 C and pressures above 2000 atm

  • PhenolsSlightly acidicNeutralized by strong bases

  • PhenolsUsed as:AntisepticDisinfectants

    First used was pure phenolproved to be too toxicMethyl derivativesCresolsCreosote

  • PhenolsDihydroxybenzenes

    Components of biochemical molecules

  • EthersDerivatives of waterBoth hydrogen atoms are replaced

    NamingSymmetricalName groups attached and add ether

  • PropertiesQuite inertAlthough react violently in the airLow boiling pointsno hydrogen bondsDiethyl etherForms a peroxide in airFirst general anesthetic