Chloroacetic acid

Chloroacetic acid is the organochlorine carboxylic acid ClCH₂COOH. Its reactive carbon–chlorine bond makes it a useful intermediate in chemical manufacturing.

Carboxylic acid: An organic compound containing a carboxyl group, –COOH, which can donate a proton. Chloroacetic acid belongs to this family and retains its characteristic acidic group.
Carboxymethyl cellulose: A water-soluble cellulose derivative bearing carboxymethyl groups. It is manufactured by introducing carboxymethyl groups using chloroacetate reagents.
Acetic acid: A two-carbon carboxylic acid with formula CH₃COOH. It lacks chlorine, providing a baseline for the substituent’s effects on acidity and reactivity.
Acetic acid chlorination: The replacement of hydrogen atoms in acetic acid with chlorine by chlorination. This reaction is a major industrial route to chloroacetic acid.
Inductive effect: The transmission of electron density through sigma bonds caused by differences in electronegativity. Chlorine withdraws electron density through the carbon chain, strengthening the acid’s conjugate base.
Thioglycolic acid: An organosulfur compound with formula HSCH₂COOH, also called mercaptoacetic acid. Replacing chlorine with sulfur-containing nucleophiles provides a route to this compound.
Dichloroacetic acid: A chlorinated acetic acid with formula Cl₂CHCOOH. Its second chlorine further withdraws electron density and increases acidity.
Hell–Volhard–Zelinsky reaction: A reaction that halogenates the alpha carbon of a carboxylic acid using phosphorus and halogen. It provides a laboratory method for making alpha-halo acids such as chloroacetic acid.
Acid dissociation constant: A measure of how readily an acid donates a proton in solution. Its value quantifies the acidity enhanced by chlorine’s inductive effect.
Phenoxyacetic acid: An aromatic ether carboxylic acid with formula C₆H₅OCH₂COOH. It can be prepared by substituting chlorine with phenoxide in chloroacetate chemistry.

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