What is the use of carbon tetraiodide in iodination?
Carbon tetraiodide is used as an iodination reagent, often upon reaction with bases. Ketones are converted to 1,1-diiodoalkenes upon treatment with triphenylphosphine (PPh 3) and carbon tetraiodide. Alcohols are converted in and to iodide, by a mechanism similar to the Appel reaction.
What is the molecular formula for carbon tetraiodide?
Carbon tetraiodide is a tetrahalomethane with the molecular formula CI 4. Being bright red, it is a relatively rare example of a highly colored methane derivative. It is only 2% by weight carbon, although other methane derivatives are known with still less carbon.
What is carbon tetrachloride used for?
Carbon tetrachloride was also widely used as a precursor to chlorofluorocarbons (CFCs). However, due to environmental concerns, the production of this compound has seen a sharp decline since the 1980s. Exposure to carbon tetrachloride is known to cause centrilobular hepatic necrosis.
What happens when carbon tetraiodide reacts with water?
Carbon tetraiodide is slightly reactive towards water, giving iodoform and I 2. It is soluble in nonpolar organic solvents. It decomposes thermally and photochemically to tetraiodoethylene, C 2 I 4.
Is carbon a Tetraiodide?
Carbon is a nonmetal, and iodide is a nonmetal; therefore, carbon and iodide form a covalent compound. Thus, the covalent molecule nomenclature rules are used. carbon tetraiodide is CI4.
What element is carbon tetraiodide?
Answer and Explanation: Carbon tetraiodide is a chemical compound with the formula CI4. This means that one molecule of carbon tetraiodide is formed from one atom of carbon... See full answer below.
What is the formula carbon tetraiodide?
CI4Carbon tetraiodide / Formula
What is CI4 called?
Carbon iodide (CI4)
Why carbon tetraiodide is unstable?
Structure. The tetrahedral molecule features C-I distances of 2.12 ± 0.02 Å. The molecule is slightly crowded with short contacts between iodine atoms of 3.459 ± 0.03 Å, and possibly for this reason, it is thermally and photochemically unstable.
Is carbon tetraiodide soluble or insoluble in water?
InsolubleCarbon tetraiodideSolubility in waterInsolubleStructureCrystal structureMonoclinicMolecular shapeTetrahedral22 more rows
Does CI4 have resonance?
0:031:20Lewis dot structure for CI4 Carbon tetraiodide - YouTubeYouTubeStart of suggested clipEnd of suggested clipWe have four of them though so four plus 28 that gives us 32 total valence electrons for CI fourMoreWe have four of them though so four plus 28 that gives us 32 total valence electrons for CI four carbons the least electronegative element here so we'll put carbon at the center.
What kind bond is CI4?
Although the bond C-I is polar in nature because of the difference of electronegativity between them but the overall CI4 molecular is nonpolar.
What is the melting point of cl4?
Carbon tetrachlorideNamesMelting point−22.92 °C (−9.26 °F; 250.23 K)Boiling point76.72 °C (170.10 °F; 349.87 K)Solubility in water0.097 g/100 mL (0 °C) 0.081 g/100 mL (25 °C)SolubilitySoluble in alcohol, ether, chloroform, benzene, naphtha, CS2, formic acid74 more rows
Can carbon bond with iodine?
Organoiodine compounds are organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare in nature.
What's the name of CCl4?
TetrachloromethaneCarbon tetrachloride / IUPAC IDCarbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is an organic compound with the chemical formula CCl4.Feb 22, 2017
Is CI4 a solid?
carbon tetraiodide (CI4) is a solid whereas carbon tetrafluoride (CF4) is a gas.
Properties, synthesis, uses
CI 4 is slightly reactive towards water, giving iodoform and I 2. Otherwise it is soluble in nonpolar organic solvents. It decomposes thermally and photochemically to tetraiodoethylene, I 2 C=CI 2. Its synthesis entails AlCl 3 -catalyzed halide exchange, which is conducted at room temperature:
Safety considerations
Manufacturers recommend that CI 4 be stored near 0 °C. As a ready source of iodine, it is an irritant. LD50: 178 mg.kg –1. In general perhalogenated organic compounds should be considered toxic.
Further reading
Sorros, H., Hinkam J. B. , “The Redistribution Reaction. XI. Application to the Preparation of Carbon Tetraiodide and Related Halides” Journal of the American Chemical Society 1945, 67, 1643. DOI.
What is the primary application of carbon tetrachloride?
Before the 1980s, the primary application of carbon tetrachloride was in the production of chlorofluorocarbons for refrigeration. It was also used as a component of fire extinguishers and as a cleaning agent.
What is the effect of carbon tetrachloride on the body?
In the body, this compound is metabolized into the trichloromethyl radical, which is highly reactive. This trichloromethyl can go on to cause hepatocellular damage.
What is CCl4 used for?
It is also used to reveal the watermarks that are placed on stamps without causing any damage to the stamp in the process. Carbon tetrachloride was also used as a component in the manufacture of lava lamps. Historically, CCl4 has been used in proton NMR spectroscopy.
What happens if you inhale carbon tetrachloride?
The inhalation of large quantities of carbon tetrachloride can cause serious damage to vital organs like the kidney and liver. It can also have negative effects on the central nervous system (CNS). Furthermore, prolonged human exposure to carbon tetrachloride often results in death. Carbon tetrachloride was also widely used as a precursor ...
What is the chemical formula for carbon tetrachloride?
Carbon tetrachloride, also known as tetrachloromethane, is an organic compound with the chemical formula CCl4. This compound is often classified as a polyhalogenated organic compound since it consists of a carbon atom which is attached to more than one halide functional group. Under standard conditions for temperature and pressure, ...
Is carbon tetrachloride a precursor to chlorofluorocarbons?
Carbon tetrachloride was also widely used as a precursor to chlorofluorocarbons (CFCs). However, due to environmental concerns, the production of this compound has seen a sharp decline since the 1980s. Exposure to carbon tetrachloride is known to cause centrilobular hepatic necrosis. In the body, this compound is metabolized into ...
Can carbon tetrachloride be decomposed?
In the presence of metals that can behave as catalysts (such as iron and aluminium), carbon tetrachloride is decomposed by water. If it is overheated steam, carbon tetrachloride can also be decomposed to create phosgene, even without the presence of a metal catalyst.
What is carbon tetrachloride used for?
Carbon tetrachloride was widely used as a dry cleaning solvent, as a refrigerant, and in lava lamps. In the last case, carbon tetrachloride is a key ingredient that adds weight to the otherwise buoyant wax.
When was carbon tetrachloride first synthesized?
Carbon tetrachloride was originally synthesized by the French chemist Henri Victor Regnault in 1839 by the reaction of chloroform with chlorine, but now it is mainly produced from methane :
What is the chemical formula for carbon tetrachloride?
Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is an organic compound with the chemical formula CCl 4.
Why did the production of carbon tetrachloride decline?
The production of carbon tetrachloride has steeply declined since the 1980s due to environmental concerns and the decreased demand for CFCs, which were derived from carbon tetrachloride. In 1992, production in the U.S./Europe/Japan was estimated at 720,000 tonnes.
Is carbon tetrachloride a solvent?
It once was a popular solvent in organic chemistry, but, because of its adverse health effects, it is rarely used today. It is sometimes useful as a solvent for infrared spectroscopy, because there are no significant absorption bands above 1600 cm −1. Because carbon tetrachloride does not have any hydrogen atoms, it was historically used in proton NMR spectroscopy. In addition to being toxic, its dissolving power is low. Its use in NMR spectroscopy has been largely superseded by deuterated solvents. Use of carbon tetrachloride in determination of oil has been replaced by various other solvents, such as tetrachloroethylene. Because it has no C–H bonds, carbon tetrachloride does not easily undergo free-radical reactions. It is a useful solvent for halogenations either by the elemental halogen or by a halogenation reagent such as N -bromosuccinimide (these conditions are known as Wohl–Ziegler bromination ).
Can carbon tetrachloride cause cancer?
Chronic exposure to carbon tetrachloride can cause liver and kidney damage and could result in cancer. See safety data sheets.
Can carbon tetrachloride be used in a wall fixture?
The carbon tetrachloride type could also be installed in a spring-loaded wall fixture with a solder -based restraint. When the solder melted by high heat, the spring would either break the globe or launch it out of the bracket, allowing the extinguishing agent to be automatically dispersed into the fire.
Overview
Carbon tetraiodide is a tetrahalomethane with the molecular formula CI4. Being bright red, it is a relatively rare example of a highly colored methane derivative. It is only 2.3% by weight carbon, although other methane derivatives are known with still less carbon.
Structure
The tetrahedral molecule features C-I distances of 2.12 ± 0.02 Å. The molecule is slightly crowded with short contacts between iodine atoms of 3.459 ± 0.03 Å, and possibly for this reason, it is thermally and photochemically unstable.
Carbon tetraiodide crystallizes in tetragonal crystal structure (a 6.409, c 9.558 (.10 nm)).
It has zero dipole moment due to its symmetrically substituted tetrahedral molecule.
Properties, synthesis, uses
Carbon tetraiodide is slightly reactive towards water, giving iodoform and I2. It is soluble in nonpolar organic solvents. It decomposes thermally and photochemically to tetraiodoethylene, C2I4. Its synthesis entails AlCl3-catalyzed halide exchange, which is conducted at room temperature:
The product crystallizes from the reaction solution.
Safety considerations
Manufacturers recommend that carbon tetraiodide be stored near 0 °C (32 °F). As a ready source of iodine, it is an irritant. Its LD50 on rats is 178 mg/kg. In general, perhalogenated organic compounds should be considered toxic, with the narrow exception of small perfluoroalkanes (essentially inert due to the strength of the C-F bond).
Further reading
• Sorros H., Hinkam J. B. (1945). "The Redistribution Reaction. XI. Application to the Preparation of Carbon Tetraiodide and Related Halides". Journal of the American Chemical Society. 67 (10): 1643. doi:10.1021/ja01226a004.