columbia大学有机化学课件 （二十二）.pptVIP

4.4Bonding in Alcoholsand Alkyl Halides Dipole Moments alcohols and alkyl halides are polar Dipole Moments alcohols and alkyl halides are polar Dipole-Dipole Attractive Forces Dipole-Dipole Attractive Forces 4.5Physical Properties of Alcohols and Alkyl Halides:Intermolecular Forces Boiling point Solubility in water Density Effect of Structure on Boiling Point 44 48 46 -42 -32 +78 0 1.9 1.7 Effect of Structure on Boiling Point 44 -42 0 Effect of Structure on Boiling Point 48 -32 1.9 Effect of Structure on Boiling Point 46 +78 1.7 Figure 4.4 Hydrogen bonding in ethanol Figure 4.4 Hydrogen bonding in ethanol Boiling point increases with increasingnumber of halogens CH3Cl -24°C CH2Cl2 40°C CHCl3 61°C CCl4 77°C But trend is not followed when halogenis fluorine CH3CH2F -32°C CH3CHF2 -25°C CH3CF3 -47°C CF3CF3 -78°C But trend is not followed when halogenis fluorine CH3CH2F -32°C CH3CHF2 -25°C CH3CF3 -47°C CF3CF3 -78°C Solubility in water Alkyl halides are insoluble in water. Methanol, ethanol, isopropyl alcohol arecompletely miscible with water. The solubility of an alcohol in waterdecreases with increasing number of carbons (compound becomesmore hydrocarbon-like). Figure 4.5 Hydrogen Bonding Between Ethanol and Water Density Alkyl fluorides and alkyl chlorides areless dense than water. Alkyl bromides and alkyl iodides are more dense than water. All liquid alcohols have densities of about 0.8 g/mL. H H H m = 1.7 D m = 1.9 D H H C O H H C Cl d+ d– d– d+ d+ m = 1.7 D m = 1.9 D d + d – d – d + d + d – d + d – d + d – d + d – d – d + d + d – d + d – d + d – CH3CH2CH3 CH3CH2F CH3CH2OH Molecularweight Boilingpoint, °C Dipolemoment, D CH3CH2CH3 Molecularweight Boilingpoint, °C Dipolemoment, D Intermolecular forcesare weak. Only intermolecular forces are induced dipole-induced dipole attractions. CH3CH2F Molecular