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Slide 1 -

Chapter 11 Reactions 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 11 2 Types of Alcohol Reactions Dehydration to alkene Oxidation to aldehyde, ketone Substitution to form alkyl halide Reduction to alkane Esterification Tosylation Williamson synthesis of ether =>

Slide 3 -

Chapter 11 3 Summary Table =>

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Chapter 11 4 Oxidation States Easy for inorganic salts CrO42- reduced to Cr2O3 KMnO4 reduced to MnO2 Oxidation: loss of H2, gain of O, O2, or X2 Reduction: gain of H2 or H-, loss of O, O2, or X2 Neither: gain or loss of H+, H2O, HX =>

Slide 5 -

Chapter 11 5 1º, 2º, 3º Carbons =>

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Chapter 11 6 Oxidation of 2° Alcohols 2° alcohol becomes a ketone Reagent is Na2Cr2O7/H2SO4 Active reagent probably H2CrO4 Color change: orange to greenish-blue =>

Slide 7 -

Chapter 11 7 Oxidation of 1° Alcohols 1° alcohol to aldehyde to carboxylic acid Difficult to stop at aldehyde Use pyridinium chlorochromate (PCC) to limit the oxidation. PCC can also be used to oxidize 2° alcohols to ketones. =>

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Chapter 11 8 3° Alcohols Don’t Oxidize Cannot lose 2 H’s Basis for chromic acid test =>

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Chapter 11 9 Other Oxidation Reagents Collins reagent: Cr2O3 in pyridine Jones reagent: chromic acid in acetone KMnO4 (strong oxidizer) Nitric acid (strong oxidizer) CuO, 300°C (industrial dehydrogenation) Swern oxidation: dimethylsulfoxide, with oxalyl chloride and hindered base, oxidizes 2 alcohols to ketones and 1 alcohols to aldehydes. =>

Slide 10 -

Chapter 11 10 Biological Oxidation Catalyzed by ADH, alcohol dehydrogenase. Oxidizing agent is NAD+, nicotinamide adenine dinucleotide. Ethanol oxidizes to acetaldehyde, then acetic acid, a normal metabolite. Methanol oxidizes to formaldehyde, then formic acid, more toxic than methanol. Ethylene glycol oxidizes to oxalic acid, toxic. Treatment for poisoning is excess ethanol. =>

Slide 11 -

Chapter 11 11 Alcohol as a Nucleophile ROH is weak nucleophile RO- is strong nucleophile New O-C bond forms, O-H bond breaks. =>

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Chapter 11 12 Alcohol as an Electrophile OH- is not a good leaving group unless it is protonated, but most nucleophiles are strong bases which would remove H+. Convert to tosylate (good leaving group) to react with strong nucleophile (base) =>  + C-Nuc bond forms, C-O bond breaks

Slide 13 -

Chapter 11 13 Formation of Tosylate Ester p-toluenesulfonyl chloride TsCl, “tosyl chloride” ROTs, a tosylate ester =>

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Chapter 11 14 SN2 Reactions of Tosylates With hydroxide produces alcohol With cyanide produces nitrile With halide ion produces alkyl halide With alkoxide ion produces ether With ammonia produces amine salt With LiAlH4 produces alkane =>

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Chapter 11 15 Summary of Tosylate Reactions =>

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Chapter 11 16 Reduction of Alcohols Dehydrate with conc. H2SO4, then add H2 Tosylate, then reduce with LiAlH4 =>

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Chapter 11 17 Reaction with HBr -OH of alcohol is protonated -OH2+ is good leaving group 3° and 2° alcohols react with Br- via SN1 1° alcohols react via SN2 =>

Slide 18 -

Chapter 11 18 Reaction with HCl Chloride is a weaker nucleophile than bromide. Add ZnCl2, which bonds strongly with -OH, to promote the reaction. The chloride product is insoluble. Lucas test: ZnCl2 in conc. HCl 1° alcohols react slowly or not at all. 2 alcohols react in 1-5 minutes. 3 alcohols react in less than 1 minute. =>

Slide 19 -

Chapter 11 19 Limitations of HX Reactions HI does not react Poor yields of 1° and 2° chlorides May get alkene instead of alkyl halide Carbocation intermediate may rearrange. =>

Slide 20 -

Chapter 11 20 Reactions with Phosphorus Halides Good yields with 1° and 2° alcohols PCl3 for alkyl chloride (but SOCl2 better) PBr3 for alkyl bromide P and I2 for alkyl iodide (PI3 not stable) =>

Slide 21 -

Chapter 11 21 Mechanism with PBr3 P bonds to -OH as Br- leaves Br- attacks backside (SN2) HOPBr2 leaves =>

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Chapter 11 22 Reaction with Thionyl Chloride Produces alkyl chloride, SO2, HCl S bonds to -OH, Cl- leaves Cl- abstracts H+ from OH C-O bond breaks as Cl- transferred to C =>

Slide 23 -

Chapter 11 23 Dehydration Reactions Conc. H2SO4 produces alkene Carbocation intermediate Saytzeff product Bimolecular dehydration produces ether Low temp, 140°C and below, favors ether High temp, 180°C and above, favors alkene =>

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Chapter 11 24 Dehydration Mechanisms =>

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Chapter 11 25 Energy Diagram, E1 =>

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Chapter 11 26 Unique Reactions of Diols Pinacol rearrangement Periodic acid cleavage =>

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Chapter 11 27 Pinacol Rearrangement Pinacol: 2,3-dimethyl-2,3-butanediol Dehydration with sulfuric acid =>

Slide 28 -

Chapter 11 28 Periodic Cleavage of Glycols Same products formed as from ozonolysis of the corresponding alkene. =>

Slide 29 -

Chapter 11 29 Esterification Fischer: alcohol + carboxylic acid Tosylate esters Sulfate esters Nitrate esters Phosphate esters =>

Slide 30 -

Chapter 11 30 Fischer Esterification Acid + Alcohol yields Ester + Water Sulfuric acid is a catalyst. Each step is reversible. =>

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Chapter 11 31 Tosylate Esters Alcohol + p-Toluenesulfonic acid, TsOH Acid chloride is actually used, TsCl =>

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Chapter 11 32 Sulfate Esters Alcohol + Sulfuric Acid =>

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Chapter 11 33 Nitrate Esters =>

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Chapter 11 34 Phosphate Esters =>

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Chapter 11 35 Phosphate Esters in DNA =>

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Chapter 11 36 Alkoxide Ions ROH + Na (or NaH) yields sodium alkoxide RO- + 1° alkyl halide yields ether (Williamson ether synthesis) =>

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Chapter 11 37 End of Chapter 11

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