Alcohols, Phenols, And Ethers.
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Transcript of Alcohols, Phenols, And Ethers.
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Alcohols and Phenols
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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.
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General Formulas
Bent moleculeCentral oxygen atomHydrogen and alkyl group attached (R) or an aryl group (Ar)
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General Formulas ContAlcoholsR-O-HPhenolsAr-OHBenzene ring with an OHEthersR-O-R
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Classification and Nomenclature of AlcoholsProperties of alcohols depend on the arrangement of the carbon atoms of the moleculePrimary (1) carbon atom
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Secondary (2) carbon atom
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Tertiary (3) carbon atom
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Classification and Nomenclature of AlcoholsPrimary AlcoholRCH2OHSecondary AlcoholR2CHOHTertiary AlcoholR3COH
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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.
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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
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Preparation of AlcoholsHydration Reactions
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Markovnikovs RuleThe hydroxyl group goes on the carbon with fewer hydrogens
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Production of alcoholsMethanol
1.7 billion gallons produced a yearUsed in formaldehyde, acetic acid, fuels (MTBE), silicones, refrigerants
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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
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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)
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Physiological Effects of AlcoholsLD50 (Lethal dose to 50% of a population)Tested on animalsVaries per species though
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MethanolCan cause permanent blindness or death in high amountsVapors are very dangerous as well
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EthanolToxic to humansAcute poisoning kills several hundred a year (drinking contests)Long term poisioningMost serious drug problem in US40 times more addicts than heroin
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Isopropyl AlcoholRubbing alcoholRapid evaporationAntisepticMore toxic than ethanol, but induces vomittingUsed for the manufacture of acetone
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Chemical Properties of AlcoholsReactionsOccur on the functional groupsMay involve hydrogen atoms as well
Dehydration Oxidation
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DehydrationRemoval of waterSulfuric acid as a catalystProduces:Ether (excess ROH) + waterAlkene (excess H2SO4) + water
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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
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Oxidation Cont
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Multifunctional Alcohols: Glycols and Glycerol
More than one hydroxyl groupPolyhydric groups Dihydric alcoholsTrihydric alcohols
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GlycolsDihydric alcohols1,2 ethanediol (ethylene glycol)HOCH2CH2OHTwo hydroxyl groupsextensive intermolecular hydrogen bondingHigher boiling pointUsed as anti-freeze
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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
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PhenolsSlightly acidicNeutralized by strong bases
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PhenolsUsed as:AntisepticDisinfectants
First used was pure phenolproved to be too toxicMethyl derivativesCresolsCreosote
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PhenolsDihydroxybenzenes
Components of biochemical molecules
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EthersDerivatives of waterBoth hydrogen atoms are replaced
NamingSymmetricalName groups attached and add ether
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PropertiesQuite inertAlthough react violently in the airLow boiling pointsno hydrogen bondsDiethyl etherForms a peroxide in airFirst general anesthetic