Related Experiment Video
Updated: Jul 20, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Formation of iodoacetic acids during cooking: interaction of iodized table salt with chlorinated drinking water
A Becalski1, B P-Y Lau, T J Schrader
1Health Canada, Health Products and Food Branch, Food Research Division, Address Locator 2203D, Ottawa, Ontario K1A 0L2, Canada. Adam_becalski@hc-sc.gc.ca
Abstract:
Iodoacetic and chloroiodoacetic acids were formed when municipal chlorinated tap water was allowed to react with iodized (with potassium iodide) table salt or with potassium iodide itself. Iodoacetic acid was recently shown to be a potent cytotoxic and genotoxic agent. For analysis, samples were extracted with t-amyl methyl ether and converted to the corresponding methyl esters using methanol and sulfuric acid. The concentration of iodoacetic acid was determined by gas chromatography-mass spectrometry (GC-MS) using an authentic standard. The identities of iodoacetic and chloroiodoacetic acids were further confirmed by gas chromatography-high-resolution mass spectrometry (GC-HRMS). Certain influences of sodium hypochlorite and humic acid as well as the concentration of potassium iodide on the yields of these acids were investigated. The concentration of iodoacetic acid in tap water samples boiled with 2 g l-1 of iodized table salt was found to be in the 1.5 microg l-1 range, whilst the concentration of chloroiodoacetic acid was estimated to be three to five times lower.
Related Concept Videos
Carboxylic Acids to Acid Chlorides
Ions as Acids and Bases
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
Factors Affecting Solubility
Precipitation of Ions
The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Alkyl Halides
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

