Chlorination Toluene

Chlorination of toluene is a chemical transformation in which chlorine replaces a hydrogen atom in methylbenzene, producing chlorinated aromatic or side-chain derivatives. The reaction pathway depends on conditions: ultraviolet light or heat promotes free-radical substitution at the benzylic methyl group, while chlorine with a Lewis acid catalyst such as FeCl3 favors electrophilic aromatic substitution on the benzene ring, directed mainly to the ortho and para positions by the methyl group. These contrasting mechanisms make chlorination of toluene a useful model for reaction selectivity, radical chemistry, and aromatic substitution. The products serve as intermediates in chemical synthesis and industrial manufacturing.

Chlorination Toluene - Related Videos

Education

JoVE Core - Organic Chemistry

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...

Research

JoVE Journal - Bioengineering

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...

Controlled-release of Chlorine Dioxide in a Perforated Packaging System to Extend the Storage Life and Improve the Safety of Grape Tomatoes

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Cited by 14 •

2017

Here, we describe a protocol for the application of a novel, slow-release ClO2 product that reduces spoilage and extends the shelf life of fresh fruit. The slow-release ClO2 product was added to standard commercial grape tomato packaging and tested against Escherichia coli and Alternaria alternata.

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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2025

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...

Oxidation-Reduction Reactions

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2020

Oxidation–Reduction Reactions Earth’s atmosphere contains about 20% molecular oxygen, O2, a chemically reactive gas that plays an essential role in the metabolism of aerobic organisms and in many environmental processes that shape the world. The term oxidation was originally used to describe chemical reactions involving O2, but its meaning has evolved to refer to a broad and important reaction class known as oxidation–reduction (redox) reactions. Some redox reactions involve the transfer of...

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