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Alcohols and Phenols Chapter 17: Alcohols and Phenols 1 Alcohols and Phenols Alcohols contain an OH group connected to a saturated C (sp3) They are important solvents and synthesis intermediates Methanol, CH3OH, called methyl alcohol, is a common solvent, a fuel additive, produced in large quantities Ethanol, CH3CH2OH, called ethyl alcohol, is a solvent, fuel, beverage Phenols contain an OH group connected to a carbon in a benzene ring. Phenol, C6H5OH (“phenyl alcohol”) has diverse uses - it gives its name to the general class of compounds Enol, contains both a double bond and OH, they do not have to be adjacent, note that the priority goes to OH, the last name. alcohol (ROH) phenol enol 2 Industrial method for making ROH Methanol (methyl alcohol, wood alcohol) causes blindness in low doses (15 mL), and death in larger doses (100 – 250 mL). Catalytic reduction: Ethanol (ethyl alcohol, grain alcohol): Non-beverage use obtained by acid-catalyzed hydration of ethylene: 3 17.1 Naming Alcohols General classifications of alcohols based on C to which OH is attached CH3OH RCH2OH R2CHOH R3COH methyl primary 1o secondary 2o tertiary 3o 4 IUPAC Rules for Naming Alcohols Select the longest carbon chain containing the hydroxyl group, and derive the parent name by replacing the -e ending of the corresponding alkane with -ol Number the chain from the end nearer the hydroxyl group Number substituents according to position on chain, listing the substituents in alphabetical order Examples of primary alcohols: CH3CH2OH ethanol (grain alcohol) CH3CH2CH2OH 1-propanol (n-propanol) CH3CH2CH2CH2OH 1-butanol (n-butanol) CH2(OH)CH2CH(CH3)2 3-methyl-1-butanol 5 Secondary Alcohols 2-propanol 2-butanol (isopropyl or rubbing alcohol) 3-pentanol cyclopentanol 6 Tertiary Alcohols 2-methyl-2-pentanol 2-methyl-2-propanol tert-butyl alcohol 1-cyclopentenol phenol 7 Give the Structure or IUPAC Name for the following: 2-chloro-3-pentanol H OH 2-phenyl-2-propanol H CH3 OH H 3-ethyl-3-hexanol OH H2C CH(CH3)2 8 Give the Structure or IUPAC Name for the following: ROH with a multiple bond 2-propen-1-ol 2-cyclohexenol (Allyl alcohol) OH H2C C C CH2CH3 More than one ROH in a compound 1,3-pentanediol OH OH OH H2C CH CH CH2 CH3 9 Naming Phenols The word phenol is used both as the name of a specific substance (hydroxybenzene) and as a family name for hydroxy-substituted aromatic compounds. Phenols are named as substituted aromatic compounds according to the rules of naming aromatic compounds. Note that –phenol is used as the parent name rather than benzene. p-methylphenol 2,4-dinitrophenol 10 Naming Phenols Problems: Write the structure for the following: m-chlorophenol 2,4,6-tribromophenol The hydroxyl group is named as a substituent when it occurs in the same molecule with carboxylic acid, aldehyde, or ketone functional groups, which have priority in naming. m-hydroxybenzoic acid p-hydroxybenzaldehyde 11 17.2 Properties of Alcohols and Phenols: Hydrogen Bonding The structure around O of the alcohol or phenol is similar to that in water, sp3 hybridized Alcohols and phenols have much higher boiling points than similar alkanes and alkyl halides 12 Common alcohols are liquids. Lower molecular weight alcohols (R-OH) are miscible (soluble) in water. As the R-group increases in size, the solubility decreases. Branching tends to increase solubility over linear alcohols of the same molecular weight (isomers). The R-groups tend to make for decreased water solubility, as they are hydrophobic. The OH group tends to increase water solubility, as it is hydrophilic. Flammability: Lower molecular weight alcohols are more flammable, have a lower flash point than higher molecular weight alcohols. However, all alcohols tend to be flammable. Acidity of Alcohols and Phenols. Alcohols are about as acidic as water. Alcohols can undergo slight dissociation reaction with water forming an alkoxide ion (RO-)and + hydronium ion (H3O ). 13 17.3 Properties of Alcohols and Phenols: Acidity and Basicity Weakly basic and weakly acidic Alcohols are weak Brønsted bases, protonated by + strong acids to yield oxonium ions, ROH2 14 Alchols and Phenols are Weak Brønsted Acids Can transfer a proton to water to a very small extent + Produces H3O and an alkoxide ion, RO , or a phenoxide ion, ArO 15 Brønsted Acidity Measurements The acidity constant, Ka, measure the extent to which a Brønsted acid transfers a proton to water + [A ] [H3O ] Ka = ————— and pKa = log Ka [HA] Relative acidities are more conveniently presented on a logarithmic scale, pKa, which is directly proportional to the free energy of the equilibrium Differences in pKa correspond to differences in free energy Compounds with small Ka (or large pKa) are less acidic. 16 pKa Values for Typical OH Compounds 17 Relative Acidities of Alcohols Simple alcohols are about as acidic as water Alkyl groups make an alcohol a weaker acid The more easily the alkoxide ion is solvated by water the more its formation is energetically favored Steric effects are important 18 Inductive Effects Electron-withdrawing groups make an alcohol a stronger acid by stabilizing the conjugate base (alkoxide) and lower pKa 19 Generating Alkoxides from Alcohols Alcohols are weak acids – requires a strong base to form an alkoxide such as NaH, sodium amide NaNH3, and Grignard reagents (RMgX) Alkoxides are bases used as reagents in organic chemistry - + CH3OH + NaH CH3O Na + H2 - + CH3CH2OH + NaNH3 CH3CH2O Na + NH3 - + CH3CH2OH + CH3MgBr CH3CH2O MgBr + CH4 + - + 2ROH + 2Na 2RO Na + H2 20 Phenol Acidity Phenols are about a million times more acidic than alcohols because the phenoxide anion is resonance stabilized. They are soluble in dilute aqueous NaOH and can often be separated from a mixture by basic extraction. Substituted Phenols can be more or less acidic than phenol itself An electron-withdrawing substituent makes a phenol more acidic by delocalizing the negative charge Phenols with an electron-donating substituent are less acidic because these substituents concentrate the charge 21 17.4 Preparation of Alcohols: an Overview Alcohols are derived from many types of compounds The alcohol hydroxyl can be converted to many other functional groups This makes alcohols useful in synthesis Nucleophilic Substitution of alkyl halide by hydroxide R-X + OH- R-OH + X- X( = Br, Cl, I) - - CH3CH2I + OH CH3CH2OH + I 22 Review: Preparation of Alcohols by Regiospecific Hydration of Alkenes Hydration of Alkenes Hydroboration/oxidation yields syn addition non- Markovnikov products. (7.5) H OH 1. BH3 H3C CH2 CH CH2 CH3 CH2 CH CH2 2. NaOH, H2O2 23 Review: Preparation of Alcohols by Regiospecific Hydration of Alkenes Hydration of Alkenes Oxymercuration/reduction yields Markovnikov product. (7.4) HO H 1. Hg(AcO)2, H2O H C CH CH CH 3 2 2 CH3 CH2 CH CH2 2. NaBH4 24 Preparation of 1,2-Diols 1,2 diols (glycol) can be prepared by OsO4 hydroxylation followed by reduction. The product has syn stereochemistry. (7.8) HO OH 1. OsO4, Pyridine H C CH CH CH 3 2 2 CH3 CH2 CH CH2 2. NaHSO3, H2O Problem: Predict the product. OOHH HH 1.1. OsO OsO4,4 ,Pyridine Pyridine 2.2. NaHSO NaHSO, ,H HOO 3 3 2 2 HH OOHH 25 Hydroxylation of alkenes to Form Glycol KMnO4 will produce a gycol under these mild conditions (syn addition): cold C C C C + KMnO4 + H2O + MnO2 + KOH brown purple OH OH glycol (1,2-diol) Recall from 7.8: These conditions produce a cleavage reaction (heat, higher conc. KMnO4, acidic conditions): H H KMnO O Terminal alkene 4 C C + CO2 + C H H3O OH O O KMnO4 Internal alkene + + 26 H3O OH HO 17.5 Alcohols from Reduction of Carbonyl Compounds Reduction of a carbonyl O [H] OH compound in general gives an alcohol C C H Note that organic reduction [H] is the generalized reactions add the equivalent reduction agent of H2 to a molecule Mechanism of Reduction - - + O : H O H3O OH C C C H H alkoxide ion intermediate 27 Reduction of Carbonyl Compounds Aldehydes produce 1o ROH Either NaBH4 (milder) or LiAlH4 (more reactive) can be used Ketones produce 2o ROH to reduce aldehydes or ketones. Only LiAlH4 for carboxylic acids and esters. Carboxylic acids or esters produce 1o ROH 28 Problem: What carbonyl compound would you reduce to obtain the following? [H] O OH O OH O HO 29 17.6 Alcohols from Reaction of Carbonyl Compounds with Grignard Reagents Alkyl, aryl, and vinylic halides react with magnesium in ether or tetrahydrofuran (THF) to generate Grignard reagents, RMgX Grignard reagents react with carbonyl compounds to yield alcohols Grignard Formation R = 1,2,3,alkyl, aryl, or vinylic ether R-X + Mg R-Mg-X X = Cl, Br, I O 1. RMgX, ether OH C + C + HOMgX 2. H3O R 30 Mechanism of the Addition of a Grignard Reagent Grignard reagents act as nucleophilic carbon anions (carbanions, : R) in adding to a carbonyl group The intermediate alkoxide is then protonated to produce the alcohol alkoxide ion intermediate Formaldehyde 1o ROH Aldehyde 2o ROH Ketone 3o ROH o o Ester 3 ROH + 1 ROH 31 Examples of Reactions of Grignard Reagents with Carbonyl Compounds O 1. CH3MgCl, ether OH C + C HOMgCl 2. H3O + H H H CH3 H O OH 1. CH3CH2CH2MgBr, ether C H C + HOMgBr + CH2CH2CH3 H CH3 2. H3O H3C OO HHOO 1.1. CH CH33CHCH22MgBr,MgBr, ether ether CC CC CHCH CHCH HOMgBrHOMgBr 2.2. H HOO++ 22 33 ++ HH33CC CCHH33 33 HH33CC CCHH33 32 Reactions of Esters and Grignard Reagents Yields tertiary alcohols in which two of the substituents carbon come from the Grignard reagent Grignard reagents do not add to carboxylic acids O OH 1. 2 CH3MgBr, ether H3C C O CH2CH3 H3C C CH3 HO CH2CH3 + + 2.
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