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Iodoform
 
 
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The compound iodoform is C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
I
Iodine

Iodine , is a chemical element that has the symbol I and atomic number 53. Naturally-occurring iodine is a single isotope with 74 neutrons....
3. A pale yellow, crystalline, volatile substance, it has a penetrating odor (in older chemistry texts, the smell is sometimes referred to as the smell of hospitals) and, analogous to chloroform
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
, sweetish taste. It is slightly soluble in glycerol
Glycerol

Glycerol is a chemical compound also commonly called glycerin or glycerine. It is a colorless, odorless, Viscosity liquid that is widely used in pharmaceutical formulations....
 and petroleum ether
Petroleum ether

Petroleum ether, also known as benzine, VM&P Naphta, Petroleum Naphta, Naptha ASTM, Petroleum Spirits, X4 or Ligroin, is a group of various volatile, highly flammable, liquid hydrocarbon mixtures used chiefly as nonpolar solvents....
, averagely soluble in chloroform
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
 and acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
, and easily soluble in benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
, alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 (78 g/l at 25 °C), acetone
Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
 (120 g/l at 25 °C) and ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
 (136 g/l at 25 °C).

as first prepared by Georges Serrulas in 1822 and its molecular formula was identified by Jean-Baptiste Dumas
Jean-Baptiste Dumas

Jean Baptiste Andr? Dumas , was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights by measuring vapor densities....
 in 1834.

Iodoform can be synthesized in the haloform reaction
Haloform reaction

The haloform reaction is a chemical reaction where a haloform is produced by the exhaustive halogenation of a methyl ketone in the presence of a Base ....
 by the reaction of iodine and sodium hydroxide with any one of these four kinds of organic compounds:

For this reason iodoform was traditionally used as a test for methyl ketone; if a methyl ketone is present in the solution, a yellow precipitate will form.






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Encyclopedia


The compound iodoform is C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
I
Iodine

Iodine , is a chemical element that has the symbol I and atomic number 53. Naturally-occurring iodine is a single isotope with 74 neutrons....
3. A pale yellow, crystalline, volatile substance, it has a penetrating odor (in older chemistry texts, the smell is sometimes referred to as the smell of hospitals) and, analogous to chloroform
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
, sweetish taste. It is slightly soluble in glycerol
Glycerol

Glycerol is a chemical compound also commonly called glycerin or glycerine. It is a colorless, odorless, Viscosity liquid that is widely used in pharmaceutical formulations....
 and petroleum ether
Petroleum ether

Petroleum ether, also known as benzine, VM&P Naphta, Petroleum Naphta, Naptha ASTM, Petroleum Spirits, X4 or Ligroin, is a group of various volatile, highly flammable, liquid hydrocarbon mixtures used chiefly as nonpolar solvents....
, averagely soluble in chloroform
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
 and acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
, and easily soluble in benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
, alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 (78 g/l at 25 °C), acetone
Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
 (120 g/l at 25 °C) and ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
 (136 g/l at 25 °C).

Synthesis

It was first prepared by Georges Serrulas in 1822 and its molecular formula was identified by Jean-Baptiste Dumas
Jean-Baptiste Dumas

Jean Baptiste Andr? Dumas , was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights by measuring vapor densities....
 in 1834.

Iodoform can be synthesized in the haloform reaction
Haloform reaction

The haloform reaction is a chemical reaction where a haloform is produced by the exhaustive halogenation of a methyl ketone in the presence of a Base ....
 by the reaction of iodine and sodium hydroxide with any one of these four kinds of organic compounds:
  • a methyl ketone
    Ketone

    In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
    : CH3COR, where R is an organic side chain
    Side chain

    A side chain in organic chemistry and biochemistry is a part of a molecule that is attached to a core structure. The placeholder R is often used as a generic placeholder for side chains, the R historically being derived from radical or rest....
    .
  • acetaldehyde
    Acetaldehyde

    Acetaldehyde is an organic compound with the chemical formula CarbonHydrogen3CHOxygen or MeCHO. It is a flammable liquid with a fruity smell....
     (ethanal): CH3CHO
  • ethanol
    Ethanol

    Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
    : CH3CH2OH
  • secondary alcohol
    Alcohol

    In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
    s: CH3CHROH, where R is an alkyl or aryl group.


For this reason iodoform was traditionally used as a test for methyl ketone; if a methyl ketone is present in the solution, a yellow precipitate will form. This is known as the iodoform test.

Reactions

Some reagents (e.g. hydroiodic acid) can convert iodoform to diiodomethane
Diiodomethane

Diiodomethane or methylene iodide is liquid halomethane insoluble in water, soluble in ether and alcohol. It has a relatively high refractive index of 1.741....
.

Also conversion to carbon dioxide
Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
 is possible. Iodoform reacts with silver nitrate
Silver nitrate

Silver nitrate, also known as lunar caustic, is a soluble chemical compound with chemical formula silverNitrogenOxygen3. This compound is a versatile precursor to many other silver compounds, such as those used in photography....
 producing carbon monoxide
Carbon monoxide

Carbon monoxide, with the chemical formula CO, is a colorless and odorless, tasteless, yet highly toxic gas. Its molecules consist of one carbon atom covalent bond to one oxygen atom....
, which is oxidized by mixture of sulfuric acid
Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
 and iodine pentaoxide.

Uses

It was used in medicine as a healing and antiseptic dressing for wounds and sores around the beginning of the 20th century, though this use is now superseded by better antiseptic
Antiseptic

Antiseptics are antimicrobials that are applied to living biological tissue/skin to reduce the possibility of infection, sepsis, or putrefaction....
s.

It is the active ingredient in many ear powders for dog
Dog

The dog is a domesticated subspecies of the Gray Wolf, a member of the Canidae family of the order Carnivora. The term is used for both feral and pet varieties....
s and cat
Cat

The cat , also known as the Domestication cat or house cat to distinguish it from other Felinae and Felidae, is a small predationy carnivore species of crepuscular mammal that is valued by humans for its companionship and its ability to hunt vermin, snakes, scorpions, and other unwanted household pests....
s, to prevent infection and facilitate removal of ear hair, along with zinc oxide
Zinc oxide

Zinc oxide is an inorganic compound with the Chemical formula ZnO. It usually appears as a white powder, nearly insoluble in water. The powder is widely used as an additive into numerous materials and products including plastics, ceramics, glass, cement, rubber , lubricants, paints, ointments, adhesives, sealants, pigments, foods , batteries,...
 and boric acid
Boric acid

Boric acid, also called boracic acid or orthoboric acid or Acidum Boricum, is a weak acid often used as an antiseptic, insecticide, flame retardant, in nuclear power plants to control the fission rate of uranium, and as a precursor of other chemical compounds....
.

See also

  • Iodoform reaction


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