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

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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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...
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NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

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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...
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

5.5K
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...
5.5K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

8.9K
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.
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Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

3.6K
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...
3.6K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

7.1K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Fabrication of 3D Carbon Microelectromechanical Systems C-MEMS
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Benzene-derived carbon nanothreads.

Thomas C Fitzgibbons1, Malcolm Guthrie2, En-shi Xu3

  • 11] Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA [2] Materials Research Institute, Pennsylvania State University, University Park, Pennsylvania 16802, USA.

Nature Materials
|September 23, 2014
PubMed
Summary

Researchers synthesized novel sp(3) carbon nanothreads from benzene under high pressure. These crystalline nanomaterials exhibit exceptional strength and stiffness, opening new avenues for advanced materials.

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Area of Science:

  • Materials Science
  • Nanotechnology
  • Solid-State Chemistry

Background:

  • Ordered low-dimensional carbon nanomaterials like fullerenes, nanotubes, and graphene possess unique properties.
  • Synthesizing ordered carbon nanomaterials via compression-induced polymerization of aromatic molecules has been challenging, yielding only amorphous products historically.

Discussion:

  • This study reports the successful synthesis of macroscopic quantities of a crystalline one-dimensional sp(3) carbon nanomaterial from benzene under high pressure.
  • The material consists of close-packed bundles of subnanometre-diameter sp(3)-bonded carbon threads capped with hydrogen, exhibiting two-dimensional crystallinity and short-range order in the third dimension.

Key Insights:

  • Characterization using X-ray and neutron diffraction, Raman spectroscopy, solid-state NMR, and transmission electron microscopy confirmed the nanothread structure.
  • First-principles calculations support the structural findings and the potential for extraordinary mechanical properties.

Outlook:

  • These sp(3) nanothreads demonstrate potential for superior strength and stiffness compared to sp(2) carbon nanotubes and conventional polymers.
  • This work introduces a new class of ordered sp(3) nanomaterials synthesized through kinetically controlled high-pressure solid-state reactions.