Solubility of alcohols

Higher alcohols become more hydrocarbon like and less water soluble 1 Octanol for example dissolves to the extent of only 1 mL m 2000 mL of water As the alkyl chain gets longer the hydrophobic effect (Section 2 17) becomes more important to the point that It more than hydrogen bonding governs the solubility of alcohols... 

Table 22.3 compares two physical properties, boiling point and water solubility, of alcohols, ethers, and alkanes of similar molar masses. Notice that—... 

The solubility of alcohols in water gradually decreases as the hydrocarbon portion of the molecule lengthens. 

There is a gradation in the solubility of alcohols in water. The lower alcohols (methanol, ethanol and propan-l-ol) are miscible with water because they can hydrogen bond with water molecules. Heptan-l-ol and longer chain alcohols are insoluble in water. So, as the chain length increases, the solubility decreases because the long non-polar hydrocarbon part of the molecule masks the polar hydroxyl group. 

Solubility of alcohols and phenols in water is due to their ability to form hydrogen bonds with water molecules as shown. The solubility decreases with increase in size of alkyl/aryl (hydro-phobic) groups. Several of the lower molecular mass alcohols are miscible with water in all proportions. 

Alcohols with three or fewer carbons atoms are miscible in water in all proportions. The solubility of alcohols in water decreases with increasing number of carbon atoms, so that alcohols with more than six carbon atoms are nearly insoluble. As the number of carbon atoms increases, the solubility in nonpolar solvents increases. 

A useful means of distinguishing between larger carboxylic acids and phenols that don t dissolve in water is that the phenols dissolve in aqueous sodium hydroxide but don t dissolve in aqueous sodium bicarbonate. Neither sodium hydroxide nor sodium bicarbonate affects the solubility of alcohols. 

Solubilities, of alcohols in water, 1046 of stereoisomers in water and in alcohol, 1047... 

Walter H. Corkern and Linda L. r Munchausen, "Solubility of Alcohols," /. Chem. Educ., Vol. 69, 1992, 928. An overhead projector demonstration. 

The oldest publication on structure-activity relationships (SARs) known to us from the literature is a paper by Cros from 1861. He compared the toxic effect of alcohols in various species after different routes of administration. He found an increase in toxic effect with decreasing water solubility, that is increasing lipophilicity. Cros was also the first to detect a maximum in activity followed by a decrease, i.e. a non-linear relationship, as a function of solubility of alcohols in water. 

Predict relative boiling points, acidities, and solubilities of alcohols and thiols. 

Kinoshita, K., Ishikawa, H., Shinoda, K. (1958) Solubility of alcohols in water determined by the surface tension measurements. Bull. Chem. Soc. Japan 31, 1081-1082. 

Refer to Table 27-8, and explain the trends in boiling points and solubilities of alcohols in water. 

Fig. 2 Solubility of alcohols in water calculated from Henry s law. (View this art in color at www.dekker.com.)...

What are the fadors that affed the solubility of alcohols... 

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