[PDF] [PDF] 131 Alcohols and Phenols 131 Alcohols and Phenols 131

We saw that the substitution can occur by SN1 or SN2 13 3 Preparation of Alcohols Copyright 2012 John Wiley Sons, Inc Klein, Organic Chemistry 1e



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[PDF] ALCOHOLS: Properties & Preparation

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[PDF] 131 Alcohols and Phenols 131 Alcohols and Phenols 131

We saw that the substitution can occur by SN1 or SN2 13 3 Preparation of Alcohols Copyright 2012 John Wiley Sons, Inc Klein, Organic Chemistry 1e

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compounds.

13.1AlcoholsandPhenols

Copyright2012JohnWiley&Sons,Inc.

Klein, Organic Chemistry 1e13 -1

•Hydroxylgroupsinnaturalcompounds.

13.1AlcoholsandPhenols

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Klein, Organic Chemistry 1e13 -2

anaromaticring.

13.1AlcoholsandPhenols

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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

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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

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Klein, Organic Chemistry 1e13 -19

alcohol. forsuchareaction.

13.2AcidityofAlcoholsandPhenols

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Klein, Organic Chemistry 1e13 -20

•RecallfromChapter3howARIOisusedto qualitativelyassessthestrengthofanacid. -Atom

13.2AcidityofAlcoholsandPhenols

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Klein, Organic Chemistry 1e13 -21

-Resonance cyclohexanol. -Showallrelevantresonancecontributors.

13.2AcidityofAlcoholsandPhenols

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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

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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

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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