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CH 3: Alcohols, Phenols, and Ethers

CH 3: Alcohols, Phenols, and Ethers. Structure Alcohol Functional Group. Alcohol functional group: -OH Also called hydroxyl group Some consider as alkyl derivative of water. Naming Alcohols. Name the longest C chain that contains the –OH group Replace the “ ane ” ending with “ ol ”

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CH 3: Alcohols, Phenols, and Ethers

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  1. CH 3: Alcohols, Phenols, and Ethers

  2. Structure Alcohol Functional Group • Alcohol functional group: -OH • Also called hydroxyl group • Some consider as alkyl derivative of water

  3. Naming Alcohols • Name the longest C chain that contains the –OH group • Replace the “ane” ending with “ol” • Number the C in the chain from the end closest to the –OH group • When numbering the –OH has priority over the numbering of multiple bonds, alkyl substituents, and halogen substituents • Name and number any other substituents.

  4. Common Names to Know IUPAC Name……..Common Name • Methanol • Ethanol • 1-propanol • 2-propanol • 1-butanol d) sec-butyl alcohol e)tert-butyl alcohol

  5. Isomerism • Constitutional Isomers • Positional isomers • 1-hexanol and 3-hexanol • Skeletal isomers • 2-butanol and tert-butyl alcohol

  6. Classification of Alcohols 10 20 30 40

  7. Physical Properties Alcohols • Polarity of alcohols • Both polar and nonpolar character • Physical properties depend upon which portion of the molecule dominates • Consider length of C chain (nonpolar) and number of –OH groups (polar)

  8. Physical Properties Alcohols • Boiling Point – page 88 • Higher than that of alkane of similar C # • Increases as length of C chain increases • Increases as # -OH groups increases • State of matter • Even small alcohols are liquids at RT

  9. Physical Properties Alcohols • Water Solubility • 1-3 C alcohols are miscible in water • Solubility drops off for straight chain alcohols with 4-5 C • Water insoluble for 6c and up with single -OH • Diols of up to 7 C are water soluble • Diols are more soluble than single –OH alcohols of similar size/structure

  10. Methyl alcohol - Methanol • Wood alcohol – used to made by the heating of wood to a high temperature in the absence of air • Used as fuel for race cars • Produces TOXIC metabolites in the body • Methanol  formaldehyde  formic acid • results in blindness, death from acidosis with ingestion of small amounts • 1 ounce, ~30 ml can result in blindness • ~100 ml is generally fatal • Reaction is catalyzed by the liver enzyme alcohol dehydrogenase • enzyme has a much higher affinity for ethanol • therefore initial treatment can be giving individual ethanol

  11. Ethyl alcohol – Ethanol • Alcohol of alcoholic beverages • Also called grain alcohol • Often made by the fermentation of grains • Also potentially toxic • ~200 ml (pure) ethanol can be fatal • Comment on denatured alcohol at some point • Metabolized by the liver enzyme alcohol dehydrogenase • Ethanol  acetaldehyde  acetic acid • Metabolites are less toxic than those of methanol • Acetaldehyde is responsible for most of the hangover symptoms • dehydration also contributes to symptoms

  12. Ethanol, continued • chronic alcohol use can cause • liver damage (cirrhosis) and more…. • memory loss • increased risk of breast cancer in women? (with ~2+ drinks/day) • addiction • FAS in infants born to moms who drank during their pregnancies • Table on page 86 shows alcohol content of common alcoholic beverages….. • VERY INTERESTING!

  13. FAS • Brains of 6 week old infants No FAS FAS

  14. FAS • Physical Characteristics • Broad, short, flat nose • No dimple above lip • Narrow eyes • Flat face

  15. Ethylene Glycol Toxicity following ingestion generally progress in three stages: • effects on the central nervous system - intoxication, lethargy, seizures, and coma • Metabolic disturbances - acidosis, hyperkalaemia, hypocalcaemia • Effects on the heart and lungs - tachycardia, hypertension, degenerative changes- and ending with renal toxicity - deposition of calcium oxalate, haematuria, necrosis, renal failure.

  16. Ethylene Glycol & Propylene Glycol • Both: • Used in anti-freeze • Colorless and odorless • It’s the additives in antifreeze that give it odor and color • ETHYLENE GLYCOL – VERY TOXIC • Sweet taste • Metabolized to form oxalic acid • Calcium oxalate crystals in kidney

  17. Propylene Glycol • Nontoxic • Metabolized to pyruvic acid

  18. Reactivity Alcohols • Combustion • Halogenation • Substitution reaction • Reagent: PX3 • heat required • Single halogenated product + phosphoric acid

  19. 3. Oxidation of Alcohols • Common oxidizing agents and evidence of a reaction: • KMnO4 • K2Cr2O7 • Primary alcohol   • Secondary alcohol  • Tertiary alcohol 

  20. 4. Dehydration Reaction • Elimination reaction • Alcohol  alkene + water • Reagent: concentrated sulfuric acid • Conditions: high temperature, 1800C • Zaitsev’s rule used topredict major product formed • At lower temps, 1400C, primary alcohols react with each other to form an ether + water • Sulfuric acid catalyst still needed

  21. Still to come…. • Phenol • Phenols • Ethers

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