Hydrogen bonds chlorinated alcohols

Chlorine bleaches react with more chromophores than oxygen bleaches. They react irreversibly with aldehydes, alcohols, ketones, carbon-carbon double bonds, acidic carbon-hydrogen bonds, nitrogen compounds, sulfur compounds, and aromatic compounds. 

Acid derivatives (esters, acid chlorides, anhydrides, nitriles, and amides) are soluble in common organic solvents such as alcohols, ethers, chlorinated alkanes, and aromatic hydrocarbons. Acid chlorides and anhydrides cannot be used in nucleophilic solvents such as water and alcohols, however, because they react with these solvents. Many of the smaller esters, amides, and nitriles are relatively soluble in water (Table 21-2) because of their high polarity and their ability to form hydrogen bonds with water. 

POCI3 chlorinations (Eq. (8)) are acid-catalyzed reactions of such reaction products]. The hydrogen bonding of azinones is related to that of iV-oxides, discussed below, and to that of ketones (with water and alcohols) and has been demonstrated by infrared measurements on pjn-idinethione in alcohols and by the electronic absorption spectra of azinones in water. 6-Chloro-l,3-dimethyl-pyrimidine-2,4-dione is rapidly aminated at 20° (with heat evolution) by methyl- or ethyl-amines, etc., in protic media (water or alcohols). 

This property depends upon the structure of the acrylic resin. Most of the resins are soluble in moderately hydrogen-bonded solvents (e.g. ketones, esters, chlorinated hydrocarbons and aromatic hydrocarbons). Resins with more alcohol chains have greater solubility in alcohols, aliphatic hydrocarbons and naphtha. 

Water miscibility can rank from complete, for the more polar, hydrogen bonding solvent types (glycols, glycolethers, lower alcohols) via intermediate (higher alcohols, ketones and esters) to hardly miscible as in the case of most apolar hydrocarbon, chlorinated hydrocarbon and ether solvent types (Table 2.13). 

---