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CHEM2213 Topic 5: Alcohols, Ethers, & Thiols Notes.docx

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Chemistry 1027A/B
Mark Workentin

Topic 5 Alcohols, Ethers, & Thiols What Are Alcohols?  Functional group of an alcohol is an –OH (hydroxyl) group bonded to an sp hybridized C atom  O atom of an alcohol is also sp hybridized  We classify alcohols as primary, secondary, tertiary depending on whether the –OH group is on a 1° / 2° / 3° C  Glycol: compound with two hydroxyl groups on different C  Because of the large difference in electronegativity between O and C and between O and H, both the C-O and O-H bonds of an alcohol are polar covalent  Alcohols are polar molecules and higher boiling points  Hydrogen Bonding: attractive force between a partial positive charge on H and partial negative charge on a nearby O, N, F atom  Increased solubility due to hydrogen bonding between alcohol molecules and water  As molecular weight increases, physical properties of alcohols become more like those of hydrocarbons What Are The Characteristic Reactions Of Alcohols?  Alcohols can function as both weak acids and weak bases  Like water, alcohols react with Li, Na, K, Mg to liberate H and form metal alkoxides  Conversion of an alcohol to an alkyl halide involves substituting halogen for –OH at a saturated C o It has been proposed that the conversion of tertiary and secondary alcohols to haloalkanes by concentrated HX occurs by an S 1 N mechanism o Add a proton and break a bond to form a stable molecule / ion, reaction of an electrophile and nucleophile to form a new covalent bond o Primary alcohols react with HX by an S 2Nmechanism, the halide ion displaces H 2 from C bearing oxonium ion  Dehydration: elimination of water from a compound o For the acid-catalyzed dehydration of 2° and 3° alcohols (E1): add a proton, break a bond to form a stable molecule / ion, take away a proton o For the acid-catalyzed dehydration of 1° alcohol (E2): add a proton, take a proton away and break a bond to form a stable molecule / ion  Hydration-dehydration reactions are reversible, competing reactions  Large amounts of water favor alcohol formation, whereas scarcity of water favors alkene formation  Oxidation of primary alcohol gives an aldehyde or a carboxylic acid  Secondary alcohols are oxidized to ketones while tertiary alcohols
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