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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...

NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

Benzene to Phenol via Cumene: Hock Process

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...

Structure of Benzene: Molecular Orbital Model

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).

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.

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...

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Updated: May 22, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

ジェイルブレーキングベンゼンジルジマー

Andrey Yu Rogachev¹, Xiao-Dong Wen, Roald Hoffmann

¹Baker Laboratory, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, United States.

Journal of the American Chemical Society

|April 28, 2012

まとめ

この要約は機械生成です。

研究者らは,4つの新しいベンゼンジンジマーを,溶融リングで提案している. これらの構造はベンゼンより安定性が低いが,重要な活性化エネルギー障壁を有し,合成可能である可能性を示唆する.

さらに関連する動画

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

Published on: May 20, 2019

Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay

Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay

Published on: February 28, 2025

関連する実験動画

Last Updated: May 22, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

Published on: May 20, 2019

Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay

Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay

Published on: February 28, 2025

科学分野:

有機化学オーガニック・ケミストリー
コンピューティング・ケミストリー
理論化学理論化学について

背景:

ベンゼン (C6H6) は基本的な芳香化合物である.
ベンゼンの反応性と潜在的誘導体の理解は,有機化学において極めて重要です.
新しい分子構造は,化学結合と安定性についての洞察を提供します.

研究の目的:

新しいベンゼン二元構造の合成の可能性を計算的に調査する.
提案されているベンゼン二重体の安定性と断片化の経路を特徴付ける.
これらのユニークな分子のための潜在的な合成経路を探求するために.

主な方法:

コンピューティング・モデリングは,4つの新しいベンゼン二元構造の設計と分析に使用されました.
エネルギープロファイルを決定するために,密度関数理論 (DFT) の計算を使用した.
リング割れ,シグマトロピクシフト,サイクル添加を含む潜在的な反応チャネルの分析が行われました.

主要な成果:

トランス融合サイクロヘクサディエンのリングを特徴とする4つの仮説的なベンゼンジルジマーが特定されました.
これらの二次は,2つの個々のベンゼン分子よりも安定性が低い50-99 kcal/molであると計算されています.
断片化のための計算された活性化エネルギーは,27 kcal/mol以上またはそれと同等であることが判明しました.

結論:

安定性が低いにもかかわらず,提案されたベンゼンジルジメルは,分解に対する実質的な運動的障壁を示しています.
様々な反応経路が探求され,一部の経路は合成の可能性を示した.
これらの新しいベンゼン二元構造が実験的に実現できるという合理的な確率があります.