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Related Concept Videos

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
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...
Alkyl Halides02:45

Alkyl Halides

Structural Properties
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...
Stimulants01:29

Stimulants

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Mass Spectrometry: Alkyl Halide Fragmentation01:22

Mass Spectrometry: Alkyl Halide Fragmentation

Chlorine isotopes exist as 35Cl and 37Cl in a 3:1 ratio, while bromine isotopes exist as 79Br and 81Br in a 1:1 ratio. The mass spectrum of alkyl halides typically produces two distinct molecular ion peaks, the molecular ion peak, [M], and the molecular ion plus two, [M + 2] peak. The relative heights of these two peaks are proportional to the isotopic abundance ratios of the halide. For example, 2‐chloropropane and 1‐bromopropane display two peaks with relative peak heights in a 3:1 and 1:1...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Related Experiment Video

Updated: Jun 28, 2026

Comparing the Effects of Electronic Cigarette Vapor and Cigarette Smoke in a Novel In Vivo Exposure System
10:44

Comparing the Effects of Electronic Cigarette Vapor and Cigarette Smoke in a Novel In Vivo Exposure System

Published on: May 24, 2017

Methyl chloride and the U.S. cigarette.

Brian J Novak1, Simone Meinardi, Donald R Blake

  • 1Department of Chemistry, University of California, Irvine, CA, USA. dr.briannovak@gmail.com

Nicotine & Tobacco Research : Official Journal of the Society for Research on Nicotine and Tobacco
|November 7, 2008
PubMed
Summary

Cigarette smoke contains high levels of methyl chloride (CH3Cl), significantly exceeding urban air concentrations. This finding highlights a potential major anthropogenic source of CH3Cl in the United States.

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Isolation of Mouse Respiratory Epithelial Cells and Exposure to Experimental Cigarette Smoke at Air Liquid Interface
10:47

Isolation of Mouse Respiratory Epithelial Cells and Exposure to Experimental Cigarette Smoke at Air Liquid Interface

Published on: February 21, 2011

Area of Science:

  • Environmental Chemistry
  • Atmospheric Chemistry
  • Public Health

Background:

  • Methyl chloride (CH3Cl) is a significant atmospheric gas.
  • Cigarette smoke composition is a public health concern.
  • Anthropogenic sources contribute to atmospheric CH3Cl levels.

Purpose of the Study:

  • To quantify methyl chloride (CH3Cl) levels in various cigarette brands.
  • To investigate the relationship between CH3Cl and combustion byproducts.
  • To assess the contribution of cigarette smoke to atmospheric CH3Cl.

Main Methods:

  • Purchase of diverse cigarette brands from Southern California retail locations.
  • Analysis of volatile gas samples using multicolumn/multidetector gas chromatography.
  • Correlation analysis of CH3Cl concentrations with carbon monoxide (CO) and carbon dioxide (CO2).

Main Results:

  • Methyl chloride (CH3Cl) levels in cigarette smoke were found to be up to four orders of magnitude higher than urban air levels.
  • CH3Cl concentrations correlated strongly with CO and CO2, indicating a link to combustion.
  • Some cigarette brands exceeded the U.S. EPA's maximum exposure limit for CH3Cl.
  • Light cigarettes showed higher CH3Cl levels compared to filtered or heavier brands.

Conclusions:

  • Cigarette smoke represents a substantial anthropogenic source of methyl chloride (CH3Cl), potentially accounting for 5% of U.S. emissions.
  • Cigarette packing density may influence CH3Cl production.
  • Elevated CH3Cl levels in smoke pose a public health concern and contribute to atmospheric pollution.