Chapter+8b - CHAPTER 8 Hydroxyl Functional Group: Alcohols:...

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CHAPTER 8 Hydroxyl Functional Group: Alcohols: Properties, Preparation, and Strategy 0f Synthesis
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Methanol is an industrial chemical . catalytic reduction Principal use: preparation of formaldehyde. End uses: solvent, fuel for camp stoves, antifreeze, fuel, synthetic intermediate . CO + 2H CO + 2H 2 CH CH 3 OH OH Highly poisonous. May lead to blindness or death. A change of catalyst leads to the production of 1,2-ethanediol: A possible precursor of gasoline.
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Ethanol is also an industrial chemical. Most ethanol comes from fermentation or the hydration of ethene . Synthetic ethanol is produced by hydration of ethylene and is denatured (made unfit for drinking) by adding methanol, benzene, pyridine, castor oil, gasoline, etc. Isopropyl alcohol Isopropyl alcohol is is prepared by hydration of propene. All alcohols with one to six carbons are readily available. Alcohol in alcoholic beverages General depressant High in calories, little nutritional value Metabolically degraded linearly with time Poisonous (lethal concentration ~ 0.4%) Near toxic dose used to treat methanol poisoning Produced by fermentation of sugars and starch
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2-Propanol: Toxic, but not absorbed through the skin Used as a rubbing alcohol, a solvent, and as a cleaning agent 1,2-Ethanediol (ethylene glycol): Used as an antifreeze (completely miscible with water) Produced from ethene:
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1,2,3-Propanetriol (glycerol, glycerine): Non-toxic Major component of fatty tissue Liberated by the action of alkali on fats to form soaps: Phosphoric esters of glycerols are major cell membrane components. Used in lotions, cosmetics, and medicinal preparations.
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IUPAC Nomenclature of Alcohols Select the longest chain containing the hydroxyl and change the suffix name of the corresponding parent alkane from -ane to –ol Number the parent to give the hydroxyl the lowest possible number substituents take their locations accordingly Common Names of simple alcohols are still often used and are approved by IUPAC
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Cyclic alcohols are called cycloalkanols and the carbon carrying the –OH group is the 1 carbon. Alcohols with two hydroxyls are called diols in IUPAC nomenclature and glycols in common nomenclature
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Structural and Physical Properties of Alcohols The structure of alcohols resembles that of water. In the structures of water, methanol, and methoxymethane, the oxygen atoms are all sp 3+ hybridized and their bond angles are all nearly tetrahedral. The O-H bond is shorter than the C-H bonds. The bond strength of the O-H bond is greater than that of the C- H bonds: •DH o O-H = 104 kcal mol -1 •DH o C-H = 98 kcal mol -1
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Physical Properties of Alcohols Alcohols have considerably higher boiling points Molecules of alcohols hydrogen bond to each other Alcohols and can hydrogen bond to water
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The acidity of alcohols resembles that of water. The acidity constant for an alcohol can be defined as:
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Chapter+8b - CHAPTER 8 Hydroxyl Functional Group: Alcohols:...

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