Reactions of Alcohols:
Acid-base reactions
Alcohols are little much weaker acids than water which means that the conjugate base that generated from an alcohol (the alkoxide ion) is a stronger base than the conjugate base of water (the hydroxide ion). The result of it is that it is not possible to generate an alkoxide ion by using sodium hydroxide as base. Alcohols do not react along with sodium bicarbonate / amines, and a stronger base like sodium hydride or sodium amide is needed to produce the alkoxide ion as shown in figure. Alcohols can also be transformed to alkoxide ions on treatment with sodium, potassium, or lithium metal. A number of organic reagents can also act as strong bases, for instance Grignard reagents and organolithium reagents.
Figure: Generation of an alkoxide ion.
Alkoxide ions are neutralized in water and thus reactions involving these reagents should be performed in the alcohol from which they were derived, that is reactions including sodium ethoxide are best performed in ethanol. Alcohols have a general pKa of 15.5-18.0 as compared to pKa values of 25 for ethyne, 38 for ammonia and 50 for ethane.