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1,Lecture 4 Alcohols, Phenols, and Thiols,Alcohols, Phenols, and Thiols,Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings,2,Midterm II Outcome,Class Average: 75High Score: 103Low Score: 32,3,Alcohols and Phenols,An alcohol containsA hydroxyl group (OH) attached to a carbon chain.A phenol containsA hydroxyl group (OH) attached to a benzene ring.,Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings,4,Alcohols 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) Secondary (2) Tertiary (3)1 group 2 groups 3 groups H CH3 CH3 | | | CH3COH CH3COH CH3COH | | | H H CH3,Classification of Alcohols,5,Classify each alcohol as (P) primary, (S) secondary, or (T) tertiary. OH |1. CH3CHCH2CH32. CH3CH2CH2OH OH | 3. CH3CH2CCH2CH3 | CH3,Learning Check,6,Naming Alcohols,The names of 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 alcohol,7,More Names of Alcohols,In IUPAC names for longer carbon 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 1,8,Some Typical Alcohols,OH |“rubbing alcohol”CH3CHCH3 2-propanol (isopropyl alcohol) antifreeze HOCH2CH2OH 1,2-ethanediol (ethylene glycol) OH | glycerolHOCH2CHCH2OH1,2,3-propanetriol,Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings,9,Learning Check,Give the IUPAC name for each of the following:1. CH3CH2CH2CH2OH OH CH3 | |2. CH3CHCHCH2CH3 3.,10,Write the structure of the following:A. 3-pentanolB. ethyl alcoholC. 3-methylcyclohexanol,Learning Check,11,Naming Phenols,To 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),12,Phenols in Medicine,PhenolIs the IUPAC name for benzene with a hydroxyl group.Is used in antiseptics and disinfectants.,phenol resorcinol 4-hexylresorcinol,13,Derivatives of Phenol,Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint.,Copyright 2007 by Pearson Education, Inc.Publishing as Benjamin Cummings,14,Write the structure of each of the following:A. 3-pentanolB. ethyl alcoholC. p-methylphenol,Learning Check,15,Thiols,Thiols 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 chain.,16,In thiols with long carbon chains, the chain is numbered to locate the SH group.CH3CH2CH2SH 1-propanethiol SH |CH3CHCH3 2-propanethiol,Naming Thiols,17,Thiols,Thiols Often have strong odors.Are used to detect gas leaks.Are found in onions, oysters, and garlic.,Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings,18,Learning Check,Draw the structure of each compound.A. 2-butanethiolB. 2-methyl-1-butanol,19,Learning Check,Name each of the following compounds: OH | A. CH3CH2 CHCH3 CH3 | B. CH3CH2CHCH2CH2OHCH3CH2CH2SH,20,Pause: Group Activity,Do the following problems on ALE 4Problem # 1, parts A to FProblem # 2, parts A to D,21,Ethers,EthersContain 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 ether,22,IUPAC Names for Ethers,In the IUPAC system, the shorter 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-methoxypropane,23,Ethers as Anesthetics,Anesthetics Inhibit pain signals to the brain.Such as ethyl ether CH3CH2OCH2CH3 were used for over a century, 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) Penthrane,24,MTBE,Methyl tert-butyl ether CH3 CH3OCCH3 CH3Is one of the most produced organic chemicals. Is a fuel additive Is used to improve gasoline combustion.Use is questioned since the discovery that MTBE has contaminated water supplies.,25,Learning Check,Draw the structure of each compound.A. diethyl etherB. ethyl methyl etherC. 2-methoxybutane,26,Cyclic Ethers,A cyclic etherContains an O atom in a carbon ring.Is called a heterocyclic compound.Typically has 5 (furan) or 6 atoms (pyran) in the ring.,furan tetrahydrofuran pyran 1,4-dioxane,27,Dioxins,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 orange) (TTCC, “dioxin”),28,Learning Check,Name each of the following:1. 2.,29,Pause: Group Activity,Do the following problems on ALE 4Problem # 1, parts G to IProblem # 2, parts E to F,30,Lecture 4,13.3 Physical Properties of Alcohols,Phenols, and Ethers,Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings,31,Boiling Points of Alcohols,Alcohols 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,32,Boiling Points of Ethers,EthersHave 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,33,Solubility of Alcohols and Ethers in Water,Alcohols and ethers are more soluble in water than alkanes because 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,34,Comparing Solubility and Boiling Points,CompoundMolarBoiling Soluble Mass Point (C) in Water?Alkane CH3CH2CH3 44-42 NoEther CH3OCH3 46-23 YesAlcohol CH3CH2OH 46 78 Yes,35,Solubility of Phenol,Phenol Is soluble in water. Has a hydroxyl group that ionizes slightly (weak acid). Is corrosive and irritating to the skin.,+ H2O + H3O+,36,Learning Check,Which compound would have the higher boilingpoint? Explain.ethyl methyl ether or 1-propanol,37,Learning Check,Which compound would be more soluble in water?Explain.ethanol or 2-pentanol,38,Pause: Group Activity,Do the following problems on ALE 4Problem # 3Problem # 4,39,Lecture 4,13.4 Reactions of Alcohols and Thiols,Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings,40,Combustion of Alcohols,Combustion is the reaction of an alcoholwith O2 to produce CO2 and H2O. 2CH3OH + 3O2 2CO2 + 4H2O + Heat,Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings,41,Dehydration of an alcohol occurs When heated with an acid catalyst.With 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 Alcohols,42,Learning Check,Write the equations for the reactions when 2-propanol undergoes: 1. combustion2. dehydration,43,Formation of Ethers,Ethers form when dehydration takes place at low temperature. H+CH3OH + HOCH3 CH3OCH3 + H2O two methanol dimethyl ether,44,Oxidation and Reduction,In 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 bonds.There is a gain of H.,45,Oxidation and Reduction,Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings,46,When 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 Aldehyde OH O | O | CH3CH CH3CH + H2O | H Ethanol Ethanal (ethyl alcohol) (acetaldehyde),Oxidation of Primary (1) Alcohols,47,Oxidation of Secondary (2) Alcohols,When 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 secondary alcohol ketone OH O O CH3CCH3 CH3CCH3 + H2O H 2-propanol (isopropyl alcohol) 2-propanone(dimethyl ketone, “acetone”),48,Oxidation of Tertiary (3)Alcohols,Tertiary alcohols do not readily oxidize. OTertiary alcoholno reaction OH O CH3CCH3no product CH3 no H on the C-OH to oxidize 2-methyl-2-propanol,49,Select the compound that would result for each reaction of CH3CH2CH2OH. O |1) CH3CH=CH2 2) CO2 + H2O 3) CH3CH2CHA. H+, heatB. OC. O2, heat,Learning Check,50,Oxidation of Ethanol i