Acid Halides

derivatives of acids in which the hydroxyl groups are replaced by halogen atoms. Examples are sulfuryl chloride, S0₂C1₂ [an acid halide of sulfuric acid, H₂S0₄—that is, SO₂(OH)₂]; thionyl chloride, SOCl₂ [an acid halide of sulfurous acid, H₂S0₃—that is, SO(OH)₂]; phosphorus trichloride, PCI₃ [an acid halide of phosphorous acid, H₃P0₃—that is, P(OH)₃]; and acetyl chloride, CH₃COCl (an acid halide of acetic acid, CH₃COOH).

Acid halides are very reactive: their halogen atoms can be easily replaced by other groups, such as —OH, —OR, —NH₂, —SH, and —CN. They hydrolyze in moist air, giving volatile hydrogen halide (they “smoke”)—for example, S0₂C1₂ + 2H₂O = H₂SO₄ + 2HCl ↑. The acid fluoride of sulfuric acid, sulfuryl fluoride, resists hydrolysis. In organic synthesis, organic acid halides are used to introduce the RCO (acyl) group into compounds (the acylation reaction):

RCOCl + HOR′ → RCOOR′ + HCl

Organic acid chlorides, which are made by treating carboxylic acids with acid chlorides of inorganic acids (PCl₃, PCl₅, and SOCl₂), are most frequently used for this type of reaction:

The acid halides of most inorganic acids, as well as the acid chlorides of the lower acyclic carboxylic acids, are liquids with very pungent odors.

单词	acid halides
释义	DictionarySeeacyl halide Acid Halides Acid Halides derivatives of acids in which the hydroxyl groups are replaced by halogen atoms. Examples are sulfuryl chloride, S0₂C1₂ [an acid halide of sulfuric acid, H₂S0₄—that is, SO₂(OH)₂]; thionyl chloride, SOCl₂ [an acid halide of sulfurous acid, H₂S0₃—that is, SO(OH)₂]; phosphorus trichloride, PCI₃ [an acid halide of phosphorous acid, H₃P0₃—that is, P(OH)₃]; and acetyl chloride, CH₃COCl (an acid halide of acetic acid, CH₃COOH). Acid halides are very reactive: their halogen atoms can be easily replaced by other groups, such as —OH, —OR, —NH₂, —SH, and —CN. They hydrolyze in moist air, giving volatile hydrogen halide (they “smoke”)—for example, S0₂C1₂ + 2H₂O = H₂SO₄ + 2HCl ↑. The acid fluoride of sulfuric acid, sulfuryl fluoride, resists hydrolysis. In organic synthesis, organic acid halides are used to introduce the RCO (acyl) group into compounds (the acylation reaction): RCOCl + HOR′ → RCOOR′ + HCl Organic acid chlorides, which are made by treating carboxylic acids with acid chlorides of inorganic acids (PCl₃, PCl₅, and SOCl₂), are most frequently used for this type of reaction: The acid halides of most inorganic acids, as well as the acid chlorides of the lower acyclic carboxylic acids, are liquids with very pungent odors.
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