Boiling Points - Philadelphia University

Boiling Points => Solubility in Water Solubility decreases as the size of the alkyl group increases. => Methanol Wood alcohol

Industrial production from synthesis gas Common industrial solvent Fuel at Indianapolis 500 Fire can be extinguished with water High octane rating Low emissions But, lower energy content =>Invisible flame Ethanol

Fermentation of sugar and starches in grains 12-15% alcohol, then yeast cells die. Distillation produces hard liquors Azeotrope: 95% ethanol, constant boiling Denatured alcohol used as solvent Gasahol: 10% ethanol in gasoline Toxic dose: 200 mL ethanol, 100 mL methanol => Propanol-2 Rubbing alcohol Catalytic hydration of propene CH2 CH CH2 + H2O 100-300 atm, 300C

catalyst CH3 CH CH3 OH => Acidity of Alcohols pKa range: 15.5-18.0 (water: 15.7) Acidity decreases as alkyl group increases. Halogens increase the acidity. Phenol is 100 million times more acidic than cyclohexanol! => Table of Ka Values

CH3 OH => Formation of Alkoxide Ions React methanol and ethanol with sodium metal (redox reaction). CH3CH2OH + Na CH3CH2O

Na 1 + /2 H2 React less acidic alcohols with more reactive potassium. (CH3)3C OH + K (CH3)3CO K + 1/2 H2

=> Formation of Phenoxide Ion Phenol reacts with hydroxide ions to form phenoxide ions - no redox is necessary. O O H + pK a = 10 OH +

HOH pK a = 15.7 => Synthesis (Review) Nucleophilic substitution of OH- on alkyl halide Hydration of alkenes water in acid solution (not very effective) oxymercuration - demercuration hydroboration - oxidation => Glycols (Review) Syn hydroxylation of alkenes

osmium tetroxide, hydrogen peroxide cold, dilute, basic potassium permanganate Anti hydroxylation of alkenes peroxyacids, hydrolysis => Organometallic Reagents Carbon is bonded to a metal (Mg or Li). Carbon is nucleophilic (partially negative). It will attack a partially positive carbon. C-X C=O A new carbon-carbon bond forms. =>

Grignard Reagents Formula R-Mg-X (reacts like R:- +MgX) Stabilized by anhydrous ether Iodides most reactive May be formed from any halide primary secondary tertiary vinyl => aryl

Some Grignard Reagents Br + ether Mg Cl CH3CHCH2CH3 + Mg CH3C CH2 Br

+ Mg ether ether MgBr MgCl CH3CHCH2CH3 CH3C CH2 MgBr

=> Organolithium Reagents Formula R-Li (reacts like R:- +Li) Can be produced from alkyl, vinyl, or aryl halides, just like Grignard reagents. Ether not necessary, wide variety of solvents can be used. => Reaction with Carbonyl R:- attacks the partially positive carbon in the carbonyl. The intermediate is an alkoxide ion. Addition of water or dilute acid protonates the alkoxide to produce an alcohol.

R C O R C O R C OH HOH => OH Synthesis of 1 Alcohols Grignard + formaldehyde yields a primary alcohol with one additional carbon. CH3

H3C C CH2 C H H CH3 H H MgBr C O H

CH3 CH2 C O MgBr H CH3 CH3 CH CH2 H

CH CH2 H CH2 C O H HOH H =>

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