有机化学Chap8 Alcohols, Phenols, Ethers(2013-醇1).pptVIP

Alcohols create hydrogen bonds with water make them easily dissolve in water. Smaller alcohols are miscible, but the molecules become bigger, the effects of alkyl groups R become stronger. We have known that the alkyl groups are water insoluble, so the bigger alcohols are difficult to dissolve in water or water insoluble. The functional group of the alcohols is the hydroxyl group, -OH. Unlike the alkyl halides, this group has two reactive covalent bonds, the C-O bond and the O-H bond. The electronegativity of oxygen is substantially greater than that of carbon and hydrogen. Consequently, the covalent bonds of this functional group are polarized so that oxygen is electron rich and both carbon and hydrogen are electrophilic, as shown in the drawing on the right. Because the alkyl group R is electron donating, the inductive effect makes the O-H bond more strong, so alcohols are more difficult to give the proton than water. When alcohols react with halogen acids, sometimes will cause rearrangement due to the produce of carbocations (carbocations tend to rearrangement to make them more stable.) 硝酸甘油可以有效地缓解心绞痛，但它的作用机理困扰了医学家、药理学家百余年， 直到80年代才因为弗奇戈特，伊格纳罗及穆拉德这三位美国药理学家的出色工作而得以解决：硝酸甘油及其他有机硝酸脂通过释放一氧化氮气体而舒张血管平滑肌，从而扩张血管。由于这一发现，弗奇戈特、伊格纳罗及穆拉德获得了1998年诺贝尔生理医学奖. These special physical properties are due to the existence of hydrogen bonding. The basic oxygen atoms form partial bonds to the acidic hydroxyl hydrogens. Hydrogen bonds are quite strong, on the order of 5 kcal/mol, a value not enough to make permanent dimeric or polymeric structures, but quite sufficient to raise the boiling points of alcohols. It needs the energy to break the hydrogen bonds to make all molecules separate reciprocally so the alcohols can boil. What we concern about is the intramolecular dehydration. So when we do homework or test paper, always give the intramolecular dehydration products in the dehydration reaction of alcohols unless we point out the reaction is intermolecular reaction. ? benzen