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Structure of Benzene: Kekulé Model

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.

Aromatic Compounds: Overview

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

Reactions at the Benzylic Position: Oxidation and Reduction

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

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Related Experiment Video

Updated: Mar 6, 2026

Generation of Electronic Cigarette Aerosol by a Third-Generation Machine-Vaping Device: Application to Toxicological Studies

Generation of Electronic Cigarette Aerosol by a Third-Generation Machine-Vaping Device: Application to Toxicological Studies

Published on: August 25, 2018

Benzene formation in electronic cigarettes.

James F Pankow^1,2, Kilsun Kim¹, Kevin J McWhirter²

¹Department of Chemistry, Portland State University, Portland, Oregon, United States of America.

|March 9, 2017

Summary

This summary is machine-generated.

Benzene, a carcinogen, forms in e-cigarette aerosols from propylene glycol and glycerol, especially at high power settings. While lower than conventional cigarettes, chronic exposure to e-cigarette benzene may pose risks.

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

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Published on: August 25, 2018

A Microcontroller Operated Device for the Generation of Liquid Extracts from Conventional Cigarette Smoke and Electronic Cigarette Aerosol

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

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

Published on: May 24, 2017

Area of Science:

Environmental Chemistry
Toxicology
Public Health

Background:

Electronic cigarettes (e-cigarettes) generate aerosols through fluid heating, potentially creating harmful degradation products.
Benzene, a known human carcinogen, is a significant concern in aerosolized substances.

Purpose of the Study:

To investigate the formation of benzene in e-cigarette aerosols.
To analyze benzene generation from specific e-cigarette fluid components and flavor chemicals.

Main Methods:

Three e-cigarette devices were utilized: a JUUL pod system and two refillable tank systems with adjustable power settings.
Benzene concentrations in e-cigarette aerosols were quantified using gas chromatography/mass spectrometry.

Main Results:

Benzene was not detected in the JUUL system.
In tank systems, benzene formed from propylene glycol (PG) and glycerol (GL), and from benzoic acid and benzaldehyde additives, particularly at higher power settings.
Benzene levels in tank systems ranged from not detected to 5000 μg/m³, significantly lower than conventional cigarettes (200,000 μg/m³), but potentially concerning compared to ambient air levels (1 μg/m³).

Conclusions:

E-cigarette aerosol composition and device settings influence benzene formation.
While benzene risks from e-cigarettes are lower than from conventional cigarettes, chronic exposure to elevated levels may pose a non-negligible health risk, especially for non-smokers.