Chlorobenzenes
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Chlorobenzenes
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. Uses Historical The major use of chlorobenzene is as an intermediate in the production of herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling solvent in industrial applications as well as in the laboratory. Chlorobenzene is nitrated on a large scale to give a mixture of 2-nitrochlorobenzene and 4-nitrochlorobenzene, which are separated. These mononitrochlorobenzenes are converted to related 2-nitrophenol, 2-nitroanisole, bis(2-nitrophenyl)disulfide, and 2-nitroaniline by nucleophilic displacement of the chloride, with respectively sodium hydroxide, sodium methoxide, sodium disulfide, and ammonia. The conversions of the 4-nitro derivative are similar. Chlorobenzene once was used in the manufacture of pesticides, most notably DDT, by reaction wi ...
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Dichlorobenzene
There are three distinct chemical compounds which are dichlorobenzenes: * 1,2-Dichlorobenzene or ''ortho''-dichlorobenzene; *1,3-Dichlorobenzene or ''meta''-dichlorobenzene; *1,4-Dichlorobenzene or ''para''-dichlorobenzene. All three isomers are colorless organic compounds with the formula CHCl. They differ structurally based on where the two chlorine atoms are attached to the ring, like bracelets with two beads of one color and four beads of another color. Biodegradation '' Rhodococcus phenolicus'' is a bacterium species able to degrade dichlorobenzene as its sole carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon ma ... source. References {{Authority control Chlorobenzenes ...
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1,4-Dichlorobenzene
1,4-Dichlorobenzene (1,4-DCB, ''p''-DCB, or ''para''-dichlorobenzene, sometimes abbreviated as PDCB or para) is an organic compound with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring. It is used as a disinfectant, pesticide, and deodorant, most familiarly in mothballs in which it is a replacement for the more traditional naphthalene because of naphthalene's greater flammability (though both chemicals have the same NFPA 704 rating). It is also used as a precursor in the production of the chemically and thermally resistant polymer poly(''p''-phenylene sulfide). Production ''p''-DCB is produced by chlorination of benzene using ferric chloride as a catalyst: :C6H6 + 2 Cl2 → C6H4Cl2 + 2 HCl The chief impurity is the 1,2 isomer. The compound can be purified by fractional crystallization, taking advantage of its relatively high melt ...
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Fluorobenzene
Fluorobenzene is the chemical compound with the formula C6H5F, often abbreviated PhF. A colorless liquid, it is a precursor to many fluorophenyl compounds. Preparation PhF was first reported in 1886 by O. Wallach at the University of Bonn, who prepared the compound in two steps. Phenyldiazonium chloride was first converted to a triazene using piperidine: : hN2l + 2 (CH2)5NH → PhN=N-N(CH2)5 + CH2)5NH2l The triazine was then cleaved with hydrofluoric acid: :PhN=N-N(CH2)5 + 2 HF → PhF + N2 + CH2)5NH2 Historical note: in Wallach's era, the element fluorine was symbolized with "Fl". Thus, his procedure is subtitled "Fluorbenzol, C6H5Fl". On the laboratory scale, PhF is prepared by the thermal decomposition of the benzenediazonium tetrafluoroborate: :PhN2BF4 → PhF + BF3 + N2 According to the procedure, solid hN2F4 is heated with a flame to initiate an exothermic reaction, which also affords boron trifluoride and nitrogen gas. Product PhF and BF3 a ...
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Sodium Methoxide
Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed by the deprotonation of methanol. Itis a widely used reagent in industry and the laboratory. It is also a dangerously caustic base. Preparation and structure Sodium methoxide is prepared by treating methanol with sodium: : The reaction is so exothermic that ignition is possible. The resulting solution, which is colorless, is often used as a source of sodium methoxide, but the pure material can be isolated by evaporation followed by heating to remove residual methanol. As a solid, sodium methoxide is polymeric, with sheet-like arrays of centers, each bonded to four oxygen centers. The structure, and hence the basicity, of sodium methoxide in solution depends on the solvent. It is a significantly stronger base in DMSO where it is more fully ionized and free of hydrogen bonding. Applications Organic synthesis Sodium methoxide is a routinely used base in organic ...
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Chlorination Benzene
Chlorination may refer to: * Chlorination reaction, a halogenation reaction using chlorine * Water chlorination Water chlorination is the process of adding chlorine or chlorine compounds such as sodium hypochlorite to water. This method is used to kill bacteria, viruses and other microbes in water. In particular, chlorination is used to prevent the spr ...
, a method of water treatment {{disambiguation ...
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Aluminium Chloride
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contaminated with iron(III) chloride, giving a yellow color. The anhydrous material is important commercially. It has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large amounts are also used in other areas of the chemical industry. The compound is often cited as a Lewis acid. It is an example of an inorganic compound that reversibly changes from a polymer to a monomer at mild temperature. Structure Anhydrous adopts three structures, depending on the temperature and the state (solid, liquid, gas). Solid has a sheet-like layered structure with cubic close-packed chloride ions. In this framework, the Al centres exhibit octahedral coordination geometry. In contrast, has a more ...
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Sulfur Dichloride
Sulfur dichloride is the chemical compound with the formula . This cherry-red liquid is the simplest sulfur chloride and one of the most common, and it is used as a precursor to organosulfur compounds. It is a highly corrosive and toxic substance, and it reacts on contact with water to form chlorine-containing acids. Chlorination of sulfur is produced by the chlorination of either elemental sulfur or disulfur dichloride. The process occurs in a series of steps, some of which are: :; ''ΔH'' = −58.2 kJ/mol :; ''ΔH'' = −40.6 kJ/mol The addition of to has been proposed to proceed via a mixed valence intermediate . undergoes even further chlorination to give , but this species is unstable at near room temperature. It is likely that several exist where ''n'' > 2. Disulfur dichloride, , is the most common impurity in . Separation of from is possible via distillation with to form an azeotrope of 99% purity, however sulfur dichloride loses chlorine slowly at room temper ...
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Ferric Chloride
Iron(III) chloride is the inorganic compound with the formula . Also called ferric chloride, it is a common compound of iron in the +3 oxidation state. The anhydrous compound is a crystalline solid with a melting point of 307.6 °C. The colour depends on the viewing angle: by reflected light the crystals appear dark green, but by transmitted light they appear purple-red. Structure and properties Anhydrous Anhydrous iron(III) chloride has the structure, with octahedral Fe(III) centres interconnected by two-coordinate chloride ligands. Iron(III) chloride has a relatively low melting point and boils at around 315 °C. The vapor consists of the dimer (like aluminium chloride) which increasingly dissociates into the monomeric (with D3h point group molecular symmetry) at higher temperature, in competition with its reversible decomposition to give iron(II) chloride and chlorine gas. Hydrates In addition to the anhydrous material, ferric chloride forms four hydrates ...
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Lewis Acid
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons. Trimethylborane (Me3B) is a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond. In the context of a specific chemical reaction between NH3 and Me3B, a lone pair from NH3 will form a dative bond with the empty orbital of Me3B to form an adduct NH3•BMe3. The terminology refers to the contributions of Gilbert N. Lewis. From p. 142: "We are inclined to think of substances as poss ...
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Electrophilic Halogenation
In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system. : A few types of aromatic compounds, such as phenol, will react without a catalyst, but for typical benzene derivatives with less reactive substrates, a Lewis acid is required as a catalyst. Typical Lewis acid catalysts include , , and . These work by forming a highly electrophilic complex which is attacked by the benzene ring. Reaction mechanism The reaction mechanism for chlorination of benzene is the same as bromination of benzene. Iron(III) bromide and iron(III) chloride become inactivated if they react with water, including moisture in the air. Therefore, they are generated by adding iron filings to bromine or chlorine. Here is the mechanism of this reaction: : The mechanism for iodination is slightly different: iodine (I2) is treated wi ...
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Aryne
Arynes and benzynes are highly reactive species derived from an aromatic ring by removal of two substituents. Arynes are examples of didehydroarenes (1,2-didehydroarenes in this case), although 1,3- and 1,4-didehydroarenes are also known. Arynes are examples of strained alkynes. Bonding in arynes The alkyne representation of benzyne is the most widely encountered. Arynes are usually described as having a strained triple bond. Geometric constraints on the triple bond in benzyne result in diminished overlap of in-plane p-orbitals, and thus weaker triple bond. The vibrational frequency of the triple bond in benzyne was assigned by Radziszewski to be 1846 cm−1, indicating a weaker triple bond than in unstrained alkyne with vibrational frequency of approximately 2150 cm−1. Nevertheless, benzyne is more like a strained alkyne than a diradical, as seen from the large singlet–triplet gap and alkyne-like reactivity. The LUMO of aryne lies much lower than the LUMO of ...
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Salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quantities in seawater. The open ocean has about of solids per liter of sea water, a salinity of 3.5%. Salt is essential for life in general, and saltiness is one of the basic human tastes. Salt is one of the oldest and most ubiquitous food seasonings, and is known to uniformly improve the taste perception of food, including otherwise unpalatable food. Salting, brining, and pickling are also ancient and important methods of food preservation. Some of the earliest evidence of salt processing dates to around 6,000 BC, when people living in the area of present-day Romania boiled spring water to extract salts; a salt-works in China dates to approximately the same period. Salt was also prized by the ancient Hebrews, Greeks, Romans, By ...
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