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1、Lecture 4 Alcohols, Phenols, and ThiolsAlcohols, Phenols, and ThiolsCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 1Midterm II OutcomeClass Average: 75High Score: 103Low Score: 322Alcohols and PhenolsAn alcohol containsA hydroxyl group (OH) attached to a carbon chain.A phe

2、nol containsA hydroxyl group (OH) attached to a benzene ring. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 3Alcohols are classified By the number of alkyl groups attached to the carbon bonded to the hydroxyl.As primary (1), secondary (2), or tertiary (3). Primary (1) Sec

3、ondary (2) Tertiary (3)1 group 2 groups 3 groups H CH3 CH3 | | | CH3COH CH3COH CH3COH | | | H H CH3Classification of Alcohols4 Classify each alcohol as (P) primary, (S) secondary, or (T) tertiary. OH |1. CH3CHCH2CH32. CH3CH2CH2OH OH | 3. CH3CH2CCH2CH3 | CH3Learning Check5Naming AlcoholsThe names of

4、alcoholsIn the IUPAC system replace -e of alkane name with -ol.that are common names use the name of the alkyl group followed by alcohol. FormulaIUPACCommon Name CH4 methaneCH3OH methanol methyl alcoholCH3CH3ethaneCH3CH2OH ethanol ethyl alcohol6More Names of AlcoholsIn IUPAC names for longer carbon

5、chains, the chain isnumbered from the end nearest the OH group.CH3CH2CH2OH 1-propanol OH CH3CHCH2CH3 2-butanol CH3 OH CH3CHCH2CH2CHCH3 5-methyl-2-hexanol6 5 4 3 2 17Some Typical Alcohols OH |“rubbing alcoholCH3CHCH3 2-propanol (isopropyl alcohol) antifreeze HOCH2CH2OH 1,2-ethanediol (ethylene glycol

6、) OH | glycerolHOCH2CHCH2OH1,2,3-propanetriolCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 8Learning CheckGive the IUPAC name for each of the following:1. CH3CH2CH2CH2OH OH CH3 | |2. CH3CHCHCH2CH3 3. 9Write the structure of the following:A. 3-pentanolB. ethyl alcoholC. 3-

7、methylcyclohexanolLearning Check10Naming PhenolsTo name a phenol with two substituents, Assign C-1 to the carbon attached to the OH.Number the ring to give the lowest numbers. Use prefixes o, m, and p for common names. Phenol 3-chlorophenol 4-bromophenol (m-chlorophenol) (p-bromophenol)11Phenols in

8、MedicinePhenolIs the IUPAC name for benzene with a hydroxyl group.Is used in antiseptics and disinfectants. phenol resorcinol 4-hexylresorcinol 12Derivatives of PhenolCompounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint.Copyright 2007 by Pearson E

9、ducation, Inc.Publishing as Benjamin Cummings 13Write the structure of each of the following:A. 3-pentanolB. ethyl alcoholC. p-methylphenolLearning Check14ThiolsThiols Are carbon compounds that contain a SH group.Are named in the IUPAC system by adding thiol to the alkane name of the longest carbon

10、chain. 15In thiols with long carbon chains, the chain is numbered to locate the SH group.CH3CH2CH2SH 1-propanethiol SH |CH3CHCH3 2-propanethiolNaming Thiols16ThiolsThiols Often have strong odors.Are used to detect gas leaks.Are found in onions, oysters, and garlic.Copyright 2007 by Pearson Education

11、, Inc. Publishing as Benjamin Cummings17Learning CheckDraw the structure of each compound.A. 2-butanethiolB. 2-methyl-1-butanol 18Learning CheckName each of the following compounds: OH | A. CH3CH2 CHCH3 CH3 | B. CH3CH2CHCH2CH2OHCH3CH2CH2SH19Pause: Group ActivityDo the following problems on ALE 4Prob

12、lem # 1, parts A to FProblem # 2, parts A to D20EthersEthersContain an O between two carbon groups.That are simple are named by listing the alkyl names in alphabetical order followed by ether CH3OCH3CH3CH2OCH3 dimethyl ether ethyl methyl ether21IUPAC Names for EthersIn the IUPAC system, the shorter

13、alkyl group and the oxygen are named as an alkoxy group attached to the longer alkane. methoxy propaneCH3OCH2CH2CH3 1 2 3Numbering the longer alkane gives1-methoxypropane22Ethers as AnestheticsAnesthetics Inhibit pain signals to the brain.Such as ethyl ether CH3CH2OCH2CH3 were used for over a centur

14、y, but caused nausea and were flammable.Developed by 1960s were nonflammable. Cl F F Cl F H HCCOCHHCCOCH F F F H F H Ethane(enflurane) Penthrane23MTBEMethyl tert-butyl ether CH3 CH3OCCH3 CH3Is one of the most produced organic chemicals. Is a fuel additive Is used to improve gasoline combustion.Use i

15、s questioned since the discovery that MTBE has contaminated water supplies.24Learning CheckDraw the structure of each compound.A. diethyl etherB. ethyl methyl etherC. 2-methoxybutane 25Cyclic EthersA cyclic etherContains an O atom in a carbon ring.Is called a heterocyclic compound.Typically has 5 (f

16、uran) or 6 atoms (pyran) in the ring.furan tetrahydrofuran pyran 1,4-dioxane26Dioxins Dioxins areA group of ethers that are highly toxic. Formed during forest fires and as industrial by-products.Often carcinogenic. 2,4,5-trichlorophenoxyacetic acid 2,3,7,8-tetrachlorodibenzodioxin(2,4,5-T; agent ora

17、nge) (TTCC, “dioxin)27Learning CheckName each of the following:1. 2. 28Pause: Group ActivityDo the following problems on ALE 4Problem # 1, parts G to IProblem # 2, parts E to F29Lecture 413.3 Physical Properties of Alcohols,Phenols, and EthersCopyright 2007 by Pearson Education, Inc. Publishing as B

18、enjamin Cummings 30Boiling Points of AlcoholsAlcohols Contain a strongly electronegative O in the OH groups. Form hydrogen bonds between alcohol molecules.Have higher boiling points than alkanes and ethers of similar mass.Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 31Bo

19、iling Points of EthersEthersHave an O atom, but no H is attached. Cannot form hydrogen bonds between ether molecules.Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 32Solubility of Alcohols and Ethers in WaterAlcohols and ethers are more soluble in water than alkanes becaus

20、e the oxygen atom hydrogen bonds with water. Alcohols with 1-4 C atoms are soluble, but alcohols with 5 or more C atoms are not. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 33Comparing Solubility and Boiling PointsCompoundMolarBoiling Soluble Mass Point (C) in Water?Alk

21、ane CH3CH2CH3 44-42 NoEther CH3OCH3 46-23 YesAlcohol CH3CH2OH 46 78 Yes34Solubility of PhenolPhenol Is soluble in water. Has a hydroxyl group that ionizes slightly (weak acid). Is corrosive and irritating to the skin. + H2O + H3O+35Learning CheckWhich compound would have the higher boilingpoint? Exp

22、lain.ethyl methyl ether or 1-propanol36Learning CheckWhich compound would be more soluble in water?Explain.ethanol or 2-pentanol37Pause: Group ActivityDo the following problems on ALE 4Problem # 3Problem # 438Lecture 413.4 Reactions of Alcohols and ThiolsCopyright 2007 by Pearson Education, Inc. Pub

23、lishing as Benjamin Cummings 39Combustion of AlcoholsCombustion is the reaction of an alcoholwith O2 to produce CO2 and H2O. 2CH3OH + 3O2 2CO2 + 4H2O + HeatCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 40Dehydration of an alcohol occurs When heated with an acid catalyst.W

24、ith the loss of H and OH from adjacent carbon atoms. H OH| | H+, heatHCCH HC=CH + H2O| | | | H H H H alcohol alkene Dehydration of Alcohols41Learning CheckWrite the equations for the reactions when 2-propanol undergoes: 1. combustion2. dehydration42Formation of EthersEthers form when dehydration tak

25、es place at low temperature. H+CH3OH + HOCH3 CH3OCH3 + H2O two methanol dimethyl ether 43Oxidation and ReductionIn the oxidation of an organic compound There is an increase in the number of CO bonds.There is a loss of H.In the reduction of an organic compound There is an decrease in the number of CO

26、 bonds.There is a gain of H.44Oxidation and Reduction Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 45When a primary alcohol is oxidized O,One H is removed from the OH. Another H is removed from the carbon bonded to the OH.An aldehyde is produced. O Primary alcohol Aldehy

27、de OH O | O | CH3CH CH3CH + H2O | H Ethanol Ethanal (ethyl alcohol) (acetaldehyde)Oxidation of Primary (1) Alcohols46Oxidation of Secondary (2) AlcoholsWhen a secondary alcohol is oxidized O,One H is removed from the OH.Another H is removed from the carbon bonded to the OH.A ketone is produced. O se

28、condary alcohol ketone OH O O CH3CCH3 CH3CCH3 + H2O H 2-propanol (isopropyl alcohol) 2-propanone(dimethyl ketone, “acetone)47Oxidation of Tertiary (3)AlcoholsTertiary alcohols do not readily oxidize. OTertiary alcoholno reaction OH O CH3CCH3no product CH3 no H on the C-OH to oxidize 2-methyl-2-propanol48Select the compound that would result for each reaction of CH3CH2CH2OH. O |1) CH3CH=CH2 2) CO2 + H2O 3) CH3CH2CHA. H+, heatB. OC. O2, heatLearning Check49Oxidation of Ethanol in the