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Cyclohexa-1,4-diene
1,4-Cyclohexadiene is an organic compound with the formula C6H8. It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called terpenoids, an example being γ-terpinene. An isomer of this compound is 1,3-cyclohexadiene. Synthesis and reactions In the laboratory, substituted 1,4-cyclohexadienes are synthesized by Birch reduction of related aromatic compounds using an alkali metal dissolved in liquid ammonia and a proton donor such as an alcohol. In this way, over reduction to the fully saturated ring is avoided. 1,4-Cyclohexadiene and its derivatives are easily aromatized, the driving force being the formation of an aromatic ring. The conversion to an aromatic system may be used to trigger other reactions, such as the Bergman cyclization The Masamune-Bergman cyclization or Masamune-Bergman reaction or Masamune-Bergman cycloaromatization is an organic reaction and more specifically a rearrangement reaction taking ...
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Cyclohexa-1,3-diene
Cyclohexa-1,3-diene is an organic compound with the formula (C2H4)(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). It is one of two isomers of cyclohexadiene, the other being 1,4-cyclohexadiene. Synthesis Cyclohexadiene is prepared by the double dehydrobromination of 1,2-dibromocyclohexane: :(CH2)4(CHBr)2 + 2 NaH → (CH2)2(CH)4 + 2 NaBr + 2 H2 Reactions Useful reactions of this diene are cycloadditions, such as the Diels-Alder reaction. Conversion of cyclohexa-1,3-diene to benzene + hydrogen is exothermic by about 25 kJ/mol in the gas phase. :cyclohexane → cyclohexa-1,3-diene + 2 H2 (Δ''H'' = +231.5 kJ/mol; endothermic) :cyclohexane → benzene + 3 H2 (Δ''H'' = +205 kJ/mol; endothermic) :cyclohexa-1,3-diene → benzene + H2 (Δ''H'' = -26.5 kJ/mol; exothermic) Compared with its isomer cyclohexa-1,4-diene, cyclohexa-1,3-diene is about 1.6 kJ/mol more stable. Cyclohexadiene and its derivatives form (diene)iron tricarbonyl com ...
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1,3-cyclohexadiene
Cyclohexa-1,3-diene is an organic compound with the formula (C2H4)(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). It is one of two isomers of cyclohexadiene, the other being 1,4-cyclohexadiene. Synthesis Cyclohexadiene is prepared by the double dehydrobromination of 1,2-dibromocyclohexane: :(CH2)4(CHBr)2 + 2 NaH → (CH2)2(CH)4 + 2 NaBr + 2 H2 Reactions Useful reactions of this diene are cycloadditions, such as the Diels-Alder reaction. Conversion of cyclohexa-1,3-diene to benzene + hydrogen is exothermic by about 25 kJ/mol in the gas phase. :cyclohexane → cyclohexa-1,3-diene + 2 H2 (Δ''H'' = +231.5 kJ/mol; endothermic) :cyclohexane → benzene + 3 H2 (Δ''H'' = +205 kJ/mol; endothermic) :cyclohexa-1,3-diene → benzene + H2 (Δ''H'' = -26.5 kJ/mol; exothermic) Compared with its isomer cyclohexa-1,4-diene, cyclohexa-1,3-diene is about 1.6 kJ/mol more stable. Cyclohexadiene and its derivatives form (diene)iron tricarbonyl ...
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Benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly Combustibility and flammability, flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a Precursor (chemistry), precursor to the manufacture of chemicals with more complex structures, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major Chemical industry, industrial che ...
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