Alkane Chlorination
Alkane Chlorination - Related Videos
02:23
Structure of Alkanes
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2023
The formation of carbon-carbon bonds leading to the creation of the carbon chain is the basis of organic chemistry. August Kekulé and Archibald Scott Couper independently developed this idea of carbon chain formation. Hydrocarbons are the simplest organic compounds composed of carbons and hydrogens. Based on the bond order between carbons, the hydrocarbons are further classified into alkanes, alkenes, and alkynes. Alkanes are the simplest hydrocarbons with sp3 hybrid carbon atoms. These sp3...
02:22
Nomenclature of Alkanes
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2023
In the late 19th-century, the number of new chemical compounds discovered increased tremendously. Hence, the necessity arose to develop a naming system for the systematic nomenclature of these newly discovered compounds. IUPAC (International Union for Pure and Applied Chemistry), established in 1919, sets rules for the nomenclature. The alkane nomenclature considers the length of the carbon chain, the number, and the location of the substituent to arrive at its systematic name. The IUPAC...
01:31
Radical Substitution: Allylic Chlorination
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2023
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
14:17
The Portable Chemical Sterilizer (PCS), D-FENS, and D-FEND ALL: Novel Chlorine Dioxide Decontamination Technologies for the Military
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Cited by 8 •
2014
The Portable Chemical Sterilizer (PCS) is a revolutionary, energy-independent, almost waterless sterilization technology for Army medical units. The PCS generates chlorine dioxide from dry reagents mixed with water on-site, at-will, and at point-of-use (PoU) in a plastic suitcase. The Disinfectant-sprayer for Foods and ENvironmentally-friendly Sanitation (D-FENS) and the Disinfectant for ENvironmentally-friendly Decontamination, All-purpose (D-FEND ALL) produce aqueous chlorine dioxide in a...
01:18
Mass Spectrometry: Long-Chain Alkane Fragmentation
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2024
The molecular ions of linear alkanes prefer to fragment at the carbon-carbon bond away from the end of the chain since the cleavage of an inner bond creates a stable carbocation and a stable radical. Consequently, the mass signals of linear alkanes feature intense peaks in the middle of the mass-to-charge ratio plot with weaker peaks on either end. The fragmentation of each carbon-carbon bond with the release of a methyl group in each splitting leads to prominent peaks in the mass spectra...
FAQs
Ultraviolet light or heat supplies the energy needed for homolytic cleavage of the Cl₂ bond. In this cleavage, the bonding electrons divide so each chlorine atom forms a reactive chlorine radical. This initiation step is essential because it creates the species that can begin hydrogen abstraction and sustain the subsequent radical chain process.
Propagation proceeds through two linked reactions. A chlorine radical abstracts hydrogen from an alkane, producing hydrogen chloride and an alkyl radical. The alkyl radical then reacts with Cl₂ to form a chloroalkane and regenerate a chlorine radical. Because a radical is regenerated, the sequence can continue through repeated cycles rather than requiring a new initiation event for every product molecule.
Termination removes reactive intermediates when radicals combine with one another. This stops individual chain sequences and contrasts with propagation, where a radical is consumed but another radical is produced. The distinction helps explain why the overall reaction mechanism contains initiation, continuing propagation steps, and eventual loss of radicals through combination.
Mixtures arise because an alkane may contain different types of C–H bonds, and substitution can occur at more than one position. The resulting products reflect which hydrogen atoms undergo abstraction and how the available sites contribute to product formation. Examining this distribution provides a way to study reaction selectivity rather than treating the reaction as completely uniform.
A conceptual workflow begins with an alkane and chlorine, followed by exposure to ultraviolet light or heat to initiate radical formation. The reaction then proceeds through hydrogen abstraction, alkyl-radical formation, and reaction with Cl₂. Product analysis focuses on the chloroalkanes formed and on whether substitution at multiple C–H sites produces a mixture.
The reaction provides a route to chloroalkanes, which serve as intermediates in chemical synthesis. Its value extends beyond product preparation because the mechanism connects observable product distributions with free-radical reactivity. In chemistry, studying the reaction therefore supports both synthetic planning and analysis of selectivity, substitution sites, and the factors shaping product mixtures.