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Slide 1 - Chapter 10 Structure and Synthesis of Alcohols Jo Blackburn Richland College, Dallas, TX Dallas County Community College District ã 2003, Prentice Hall Organic Chemistry, 5th Edition L. G. Wade, Jr.
Slide 2 - Chapter 10 2 Structure of Alcohols Hydroxyl (OH) functional group Oxygen is sp3 hybridized. =>
Slide 3 - Chapter 10 3 Classification Primary: carbon with –OH is bonded to one other carbon. Secondary: carbon with –OH is bonded to two other carbons. Tertiary: carbon with –OH is bonded to three other carbons. Aromatic (phenol): -OH is bonded to a benzene ring. =>
Slide 4 - Chapter 10 4 Classify these: =>
Slide 5 - Chapter 10 5 IUPAC Nomenclature Find the longest carbon chain containing the carbon with the -OH group. Drop the -e from the alkane name, add -ol. Number the chain, starting from the end closest to the -OH group. Number and name all substituents. =>
Slide 6 - Chapter 10 6 Name these: 2-methyl-1-propanol 2-methyl-2-propanol 2-butanol 3-bromo-3-methylcyclohexanol =>
Slide 7 - Chapter 10 7 Unsaturated Alcohols Hydroxyl group takes precedence. Assign that carbon the lowest number. Use alkene or alkyne name. 4-penten-2-ol (old) pent-4-ene-2-ol (1997 revision of IUPAC rules) =>
Slide 8 - Chapter 10 8 Naming Priority Acids Esters Aldehydes Ketones Alcohols Amines Alkenes Alkynes Alkanes Ethers Halides =>
Slide 9 - Chapter 10 9 Hydroxy Substituent When -OH is part of a higher priority class of compound, it is named as hydroxy. Example: 4-hydroxybutanoic acid also known as GHB =>
Slide 10 - Chapter 10 10 Common Names Alcohol can be named as alkyl alcohol. Useful only for small alkyl groups. Examples: isobutyl alcohol sec-butyl alcohol =>
Slide 11 - Chapter 10 11 Naming Diols Two numbers are needed to locate the two -OH groups. Use -diol as suffix instead of -ol. 1,6-hexanediol =>
Slide 12 - Chapter 10 12 Glycols 1, 2 diols (vicinal diols) are called glycols. Common names for glycols use the name of the alkene from which they were made. 1,2-ethanediol ethylene glycol 1,2-propanediol propylene glycol =>
Slide 13 - Chapter 10 13 Naming Phenols -OH group is assumed to be on carbon 1. For common names of disubstituted phenols, use ortho- for 1,2; meta- for 1,3; and para- for 1,4. Methyl phenols are cresols. 3-chlorophenol meta-chlorophenol 4-methylphenol para-cresol =>
Slide 14 - Chapter 10 14 Physical Properties Unusually high boiling points due to hydrogen bonding between molecules. Small alcohols are miscible in water, but solubility decreases as the size of the alkyl group increases. =>
Slide 15 - Chapter 10 15 Boiling Points =>
Slide 16 - Chapter 10 16 Solubility in Water Solubility decreases as the size of the alkyl group increases. =>
Slide 17 - Chapter 10 17 Methanol “Wood alcohol” Industrial production from synthesis gas Common industrial solvent Fuel at Indianapolis 500 Fire can be extinguished with water High octane rating Low emissions But, lower energy content Invisible flame =>
Slide 18 - Chapter 10 18 Ethanol Fermentation of sugar and starches in grains 12-15% alcohol, then yeast cells die. Distillation produces “hard” liquors Azeotrope: 95% ethanol, constant boiling Denatured alcohol used as solvent Gasahol: 10% ethanol in gasoline Toxic dose: 200 mL ethanol, 100 mL methanol =>
Slide 19 - Chapter 10 19 2-Propanol “Rubbing alcohol” Catalytic hydration of propene =>
Slide 20 - Chapter 10 20 Acidity of Alcohols pKa range: 15.5-18.0 (water: 15.7) Acidity decreases as alkyl group increases. Halogens increase the acidity. Phenol is 100 million times more acidic than cyclohexanol! =>
Slide 21 - Chapter 10 21 Table of Ka Values =>
Slide 22 - Chapter 10 22 Formation of Alkoxide Ions React methanol and ethanol with sodium metal (redox reaction). React less acidic alcohols with more reactive potassium. =>
Slide 23 - Chapter 10 23 Formation of Phenoxide Ion Phenol reacts with hydroxide ions to form phenoxide ions - no redox is necessary. O H + O H O + H O H p K a = 1 0 p K a = 1 5 . 7 =>
Slide 24 - Chapter 10 24 Synthesis (Review) Nucleophilic substitution of OH- on alkyl halide Hydration of alkenes water in acid solution (not very effective) oxymercuration - demercuration hydroboration - oxidation =>
Slide 25 - Chapter 10 25 Glycols (Review) Syn hydroxylation of alkenes osmium tetroxide, hydrogen peroxide cold, dilute, basic potassium permanganate Anti hydroxylation of alkenes peroxyacids, hydrolysis =>
Slide 26 - Chapter 10 26 Organometallic Reagents Carbon is bonded to a metal (Mg or Li). Carbon is nucleophilic (partially negative). It will attack a partially positive carbon. C - X C = O A new carbon-carbon bond forms. =>
Slide 27 - Chapter 10 27 Grignard Reagents Formula R-Mg-X (reacts like R:- +MgX) Stabilized by anhydrous ether Iodides most reactive May be formed from any halide primary secondary tertiary vinyl aryl =>
Slide 28 - Chapter 10 28 Some Grignard Reagents =>
Slide 29 - Chapter 10 29 Organolithium Reagents Formula R-Li (reacts like R:- +Li) Can be produced from alkyl, vinyl, or aryl halides, just like Grignard reagents. Ether not necessary, wide variety of solvents can be used. =>
Slide 30 - Chapter 10 30 Reaction with Carbonyl R:- attacks the partially positive carbon in the carbonyl. The intermediate is an alkoxide ion. Addition of water or dilute acid protonates the alkoxide to produce an alcohol. =>
Slide 31 - Chapter 10 31 Synthesis of 1° Alcohols Grignard + formaldehyde yields a primary alcohol with one additional carbon. =>
Slide 32 - Chapter 10 32 Synthesis of 2º Alcohols Grignard + aldehyde yields a secondary alcohol. =>
Slide 33 - Chapter 10 33 Synthesis of 3º Alcohols Grignard + ketone yields a tertiary alcohol. =>
Slide 34 - Chapter 10 34 How would you synthesize… =>
Slide 35 - Chapter 10 35 Grignard Reactions with Acid Chlorides and Esters Use two moles of Grignard reagent. The product is a tertiary alcohol with two identical alkyl groups. Reaction with one mole of Grignard reagent produces a ketone intermediate, which reacts with the second mole of Grignard reagent. =>
Slide 36 - Chapter 10 36 Grignard + Acid Chloride (1) Ketone intermediate => Grignard attacks the carbonyl. Chloride ion leaves.
Slide 37 - Chapter 10 37 Grignard and Ester (1) Grignard attacks the carbonyl. Alkoxide ion leaves! ? ! Ketone intermediate =>
Slide 38 - Chapter 10 38 Second step of reaction Second mole of Grignard reacts with the ketone intermediate to form an alkoxide ion. Alkoxide ion is protonated with dilute acid. =>
Slide 39 - Chapter 10 39 How would you synthesize... Using an acid chloride or ester. =>
Slide 40 - Chapter 10 40 Grignard Reagent + Ethylene Oxide Epoxides are unusually reactive ethers. Product is a 1º alcohol with 2 additional carbons. =>
Slide 41 - Chapter 10 41 Limitations of Grignard No water or other acidic protons like O-H, N-H, S-H, or -C—C-H. Grignard reagent is destroyed, becomes an alkane. No other electrophilic multiple bonds, like C=N, C—N, S=O, or N=O. =>
Slide 42 - Chapter 10 42 Reduction of Carbonyl Reduction of aldehyde yields 1º alcohol. Reduction of ketone yields 2º alcohol. Reagents: Sodium borohydride, NaBH4 Lithium aluminum hydride, LiAlH4 Raney nickel =>
Slide 43 - Chapter 10 43 Sodium Borohydride Hydride ion, H-, attacks the carbonyl carbon, forming an alkoxide ion. Then the alkoxide ion is protonated by dilute acid. Only reacts with carbonyl of aldehyde or ketone, not with carbonyls of esters or carboxylic acids. =>
Slide 44 - Chapter 10 44 Lithium Aluminum Hydride Stronger reducing agent than sodium borohydride, but dangerous to work with. Converts esters and acids to 1º alcohols. =>
Slide 45 - Chapter 10 45 Comparison of Reducing Agents LiAlH4 is stronger. LiAlH4 reduces more stable compounds which are resistant to reduction. =>
Slide 46 - Chapter 10 46 Catalytic Hydrogenation Add H2 with Raney nickel catalyst. Also reduces any C=C bonds. =>
Slide 47 - Chapter 10 47 Thiols (Mercaptans) Sulfur analogues of alcohols, -SH. Named by adding -thiol to alkane name. The -SH group is called mercapto. Complex with heavy metals: Hg, As, Au. More acidic than alcohols, react with NaOH to form thiolate ion. Stinks! =>
Slide 48 - Chapter 10 48 Thiol Synthesis Use a large excess of sodium hydrosulfide with unhindered alkyl halide to prevent dialkylation to R-S-R. =>
Slide 49 - Chapter 10 49 Thiol Oxidation Easily oxidized to disulfides, an important feature of protein structure. Vigorous oxidation with KMnO4, HNO3, or NaOCl, produces sulfonic acids. =>
Slide 50 - Chapter 10 50 End of Chapter 10