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compounds.
13.1AlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -1
•Hydroxylgroupsinnaturalcompounds.
13.1AlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -2
anaromaticring.
13.1AlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -3
Chapter4tonamealka
neswithminormodifications: the-OHisattachedto.
2.Identifyandnamethesubstituents.
possible.
4.Listthenumberedsubstituentsbeforethe
parentnamein alphabetically. nameorjustbeforetheͲolsuffix.
13.1AlcoholsandPhenols-
Nomenclature
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -4•Alcoholsarenamedusingthesameprocedurewe usedinChapter4tonamealka neswithminor modifications:
1.Identifytheparentchain.
2.Identifyandnamethesubstituents.
13.1AlcoholsandPhenols-
Nomenclature
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -5•Alcoholsarenamedusingthesameprocedurewe usedinChapter4tonamealkaneswithminor modifications:
13.1AlcoholsandPhenols-
Nomenclature
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -6
usedinChapter4tonamealkaneswithminor modifications: orjustbeforetheͲolsuffix. •RorSconfigurations shouldbeshownat thebeginningofthe name.
13.1AlcoholsandPhenols-
Nomenclature
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -7
1,sooftenthelocantisassumedandomitted.
used:
13.1AlcoholsandPhenols-
Nomenclature
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -8
carbontheyareattachedto: •WHYdoweusetheseclassifications?
13.1AlcoholsandPhenols-
Nomenclature
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -9
parentnameisPHENOL. •PracticewithSKILLBUILDER13.1.
13.1AlcoholsandPhenols-
Nomenclature
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -10
•Namethefollowingmolecule. isopropylͲ1,4Ͳcyclohexadiol
13.1AlcoholsandPhenols-
Nomenclature
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -11
HO Cl Br •Methanol(CH 3
OH)isthemostsimplealcohol.
methanolaremadeindustriallyfromCO 2 andH 2 every year.
1.Solvent
2.Precursorforchemicalsyntheses
3.Fuel
13.1AlcoholsandPhenols-
CommerciallyImportantAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -12
•Ethanol(CH 3 CH 2
OH)hasbeenproducedby
fermentationforthousandsofyears.HOW? year. •Ethanolhasmanyusesas:
2.Humanconsumption - ethanolsuitablefordrinkingis
howdoyouavoidthetax? •Isitpoisonous?
13.1AlcoholsandPhenols-
CommerciallyImportantAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -13
catalyzedhydrationofpropylene.
1.Industrialsolvent
2.Antiseptic
3.Gasolineadditive
13.1AlcoholsandPhenols-
CommerciallyImportantAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -14
physicalproperties. •Comparetheboilingpointsbelow. •Explainthedifferences.
13.1AlcoholsandPhenols-Physical
PropertiesofAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -15
groupscanattractwatermoleculesstrongly. (theymixinanyratio).WHY? withwater.
13.1AlcoholsandPhenols-Physical
PropertiesofAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -16
generallyinsolubleinwater? miscible. sizeofthehydrophobicgroupincreases.
13.1AlcoholsandPhenols-Physical
PropertiesofAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -17
dependsonthesizeofthehydrophobicgroup. •Tokillabacterium,the alcoholshouldhave somewatersolubility. WHY? •Tokillabacterium,the alcoholshouldhavea significanthydrophobic region.WHY?
13.1AlcoholsandPhenols-Physical
PropertiesofAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -18
antifungalagent. hydrophilicregions. -Ithassignificantwatersolubility.
13.1AlcoholsandPhenols-Physical
PropertiesofAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -19
alcohol. forsuchareaction.
13.2AcidityofAlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -20
•RecallfromChapter3howARIOisusedto qualitativelyassessthestrengthofanacid. -Atom
13.2AcidityofAlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -21
-Resonance cyclohexanol. -Showallrelevantresonancecontributors.
13.2AcidityofAlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -22
•GiventherelativelylowpK a ofphenols,willNaOHbea strongenoughbasetodeprotonateaphenol?
13.2AcidityofAlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -23
inductionwon'tbeverysignificant. reside?Howdoesthateffectacidity?
13.2AcidityofAlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -24
acidity. pK a values. •Whichofthealcoholsbelowisstronger?
13.2AcidityofAlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -25
whysolvationisastabilizingeffect. •PracticewithSKILLBUILDER13.2.
13.2AcidityofAlcoholsandPhenols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -26
moleculesinorderofincreasingpK a
13.2AcidityofAlcoholsandPhenols
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Klein, Organic Chemistry 1e13 -27
yieldanalcohol. transformation? N 1orS N 2.
13.3PreparationofAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -28
•TheS N
1processgenerallyusesaweaknucleophile
(H 2
O),whichmakestheprocessrelativelyslow.
N 1 conditions?
13.3PreparationofAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -29
alkenes. -Howdoyouavoidrearrangements? •PracticewithCONCEPTUALCHECKPOINTs
13.7and13.8.
13.3PreparationofAlcohols
Copyright2012JohnWiley&Sons,Inc.
Klein, Organic Chemistry 1e13 -30
ofacarbonyl.Whatisacarbonyl? bookkeeping. electronbookkeeping: anotheratom. -Whatistheformalchargeoncarboninquotesdbs_dbs14.pdfusesText_20