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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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 Derivatives01:37

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 Process01:27

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 Model01:18

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 Model01:07

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 Hydrogenation01:28

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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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Dímero de benceno para el desbloqueo de la cárcel.

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
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores proponen cuatro nuevos dímeros de benceno con anillos fusionados. Estas estructuras son menos estables que el benceno, pero poseen importantes barreras de energía de activación, lo que sugiere que podrían ser sintetizables.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Química computacional es la química computacional.
  • Química teórica es la química teórica.

Sus antecedentes:

  • El benceno (C6H6) es un compuesto aromático fundamental.
  • Comprender la reactividad del benceno y sus derivados potenciales es crucial en la química orgánica.
  • Las nuevas estructuras moleculares ofrecen información sobre los enlaces químicos y la estabilidad.

Objetivo del estudio:

  • Para investigar computacionalmente la viabilidad de sintetizar nuevas estructuras de dímeros de benceno.
  • Caracterizar las vías de estabilidad y fragmentación de los dimeros de benceno propuestos.
  • Para explorar posibles rutas sintéticas para estas moléculas únicas.

Principales métodos:

  • El modelado computacional se utilizó para diseñar y analizar cuatro nuevas estructuras de dímeros de benceno.
  • Se emplearon cálculos de la Teoría Funcional de Densidad (DFT) para determinar los perfiles de energía.
  • Se realizó un análisis de los posibles canales de reacción, incluida la escisión del anillo, los desplazamientos sigmatrópicos y las cicloadiciones.

Principales resultados:

  • Se identificaron cuatro dimeros hipotéticos de benceno, con anillos de ciclohexadieno trans fusionados.
  • Estos dímeros se calculan para ser de 50-99 kcal / mol menos estables que dos moléculas individuales de benceno.
  • Se encontró que las energías de activación computarizadas para la fragmentación eran mayores o iguales a 27 kcal/mol.

Conclusiones:

  • A pesar de su menor estabilidad, los dimeros de benceno propuestos exhiben importantes barreras cinéticas a la descomposición.
  • Se exploraron varias vías de reacción, con algunos canales que indican potencial para la síntesis.
  • Existe una probabilidad razonable de que estas nuevas estructuras de dímeros de benceno se puedan realizar experimentalmente.