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Lecture Organic chemistry - Chapter 8: Alcohols

Lecture Organic chemistry - Chapter 8: Alcohols. The main contents of this chapter include all of the following: Ethanol, cyclic alcohols are called cycloalkanols, physical properties, hydrogen bonding, synthesis of alcohols R-OH,.and other contents. | O Chapter 8: Alcohols R OH H H O CH3 CH3 δ+ O H CH3 δ+ δ+ δ+ δ+ δ+ δ-- δ-- δ-- Water An alcohol An ether Ethanol Industrial Building Block, Fuel Beverage Ethanol plant in West Burlington, Iowa Abuse Initial dose causes euphoria, but alcohol is a general CNS active depressant drug. Macbeth: Act 2, Scene 3, Page 2 MACDUFF . It provokes the desire, but it takes away the performance. 8/11/2015 © University of California 4 Absorption: 20% stomach, 80% gastrointestinal. Food slows it, but what is in, stays in Distribution through the body and brain is fast. Intravenous can be lethal: sudden depression of the respiratory system, brain centers. Excretion: Lungs Alcoholic breath; 5% in urine. Metabolism: Zero order in ROH! Linear with time; 10 mL/h (cocktail/hour); by oxidation: CH3CH2OH CH3CH CO2 Poisonous Second step is prevented by antabuse (disulfiram): O Enzyme Enzyme Common misconceptions: 1. Not a stimulant 2. Doesn’t warm you 3. Doesn’t help your sleep 4. Not an aphrodisiac 1. Find | O Chapter 8: Alcohols R OH H H O CH3 CH3 δ+ O H CH3 δ+ δ+ δ+ δ+ δ+ δ-- δ-- δ-- Water An alcohol An ether Ethanol Industrial Building Block, Fuel Beverage Ethanol plant in West Burlington, Iowa Abuse Initial dose causes euphoria, but alcohol is a general CNS active depressant drug. Macbeth: Act 2, Scene 3, Page 2 MACDUFF . It provokes the desire, but it takes away the performance. 8/11/2015 © University of California 4 Absorption: 20% stomach, 80% gastrointestinal. Food slows it, but what is in, stays in Distribution through the body and brain is fast. Intravenous can be lethal: sudden depression of the respiratory system, brain centers. Excretion: Lungs Alcoholic breath; 5% in urine. Metabolism: Zero order in ROH! Linear with time; 10 mL/h (cocktail/hour); by oxidation: CH3CH2OH CH3CH CO2 Poisonous Second step is prevented by antabuse (disulfiram): O Enzyme Enzyme Common misconceptions: 1. Not a stimulant 2. Doesn’t warm you 3. Doesn’t help your sleep 4. Not an aphrodisiac 1. Find the longest chain containing the –OH function: alkane alkanol. Note: This may not be the longest chain in the molecule! 2. Number from the end closest to HO-C 3. Other rules same as in alkanes 4,4-Dimethyl-1-nonanol 5-Bromo-3-propyl-2-heptanol OH OH Br 1 2 3 4 5 6 7 8 9 1 2 3 4 5 6 Names 7 OH OH CH3 HO Cyclohexanol cis-3-Methyl-cyclohexanol 1-Ethylcyclo-pentanol -OH as a substituent is called hydroxy -OR is alkoxy: ethers R-O-R’ = alkoxyalkanes RCH2OH RCHOH R’ RCOH R’ R’’ Primary Secondary Tertiary alcohol Defined as C1, # is not necessary in name 1 1 3 Cyclic Alcohols Are Called Cycloalkanols Structure O can be thought of as sp3-hybridized, “tetrahedral”, i.e. bent, not linear. Due to electron repulsion by lone pairs. O is relatively e-negative, draws bonding electrons: short = strong bonds. H H3C O DHº = 119 kcal mol-1 Most striking: Relatively high melting and boiling points, and water solubility. Why? Physical Properties Hydrogen Bonding O R H H O R δ- δ- δ+ δ+ 5 kcalmol-1 .