Related Experiment Video
Updated: Aug 14, 2026

High Content Screening Analysis to Evaluate the Toxicological Effects of Harmful and Potentially Harmful Constituents (HPHC)
Published on: May 10, 2016
Potential halogenated industrial carcinogenic and mutagenic chemicals. III. Alkane halides, alkanols and ethers
Abstract:
A variety of alkane halides, alkanols and ethers, analogous to the previously considered halogenated unsaturated (Part I) and saturated hydrocarbons (Part II) possess significant utility in a broad spectrum of applications including: solvents, fumigants, propellants and intermediates in the production of other chemicals, textiles, plastics and ion-exchange resins. Ethylene dichloride and dibromide, propylene dichloride; dibromochloropropane; 2-chloroethanol; 1-chloro-2-propanol; 2,3-dibromo-1-propanol; bis(chloromethyl)-, chloromethyl methyl-, bis(2-chloroisopropyl)-, and bis(2-chloroethyl-ethers were reviewed principally in terms of their synthesis, areas of utility, stability, distribution, reactivity, levels of exposure, population at risk, metabolism, carcinogenicity and mutagenicity.
More Related Videos
Related Concept Videos
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...
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Formation of Halohydrin from Alkenes
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Electrophilic Addition to Alkynes: Hydrohalogenation
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...

