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Diethyl ether or simply ether is an organic compound in the ether class with the formula (C2H5)2O. The discovery of ether is credited to the German physician and botanist Valerius cords in 1515- 1554. Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. It is the most common member of a class of chemical compounds known generically as ethers. It is an isomer of butanol. It is used as a solvent and was used in the past as a general anesthetic. It is sparingly soluble in water. Given its high flammability and volatility, it should be kept away from open flames and electrically heated devices.
Diethyl ether is an ether in which the oxygen atom is linked to two ethyl groups. It has a role as an inhalation anesthetic, a non-polar solvent and a refrigerant. It is a volatile organic compound and an ether. Ethers are a class of organic compounds that contain an ether group. An ether group is an oxygen atom connected to two alkyl or aryl groups. They follow the general formula R-O-R’. The C-O-C linkage is characterized by bond angles of 104.5 degrees, with the C-O distances being about 140 pm. The oxygen of the ether is more electronegative than the carbons. Thus, the alpha hydrogens are more acidic than in regular hydrocarbon chains.
What is diethyl ether?
Diethyl ether is also known as ethyl ether, a well-known anesthetic commonly called simply either an organic compound belonging to a large group of compounds called ethers. Its molecular structure consists of two ethyl groups linked through an oxygen atom as in C2H5OC2H5. IUPAC name of diethyl ether is ethoxyethane.
Structure and chemical formula of diethyl ether:
An ether group is an oxygen atom connected to two alkyl or aryl groups. They follow the general formula R-O-R’. The C-O-C linkage is characterized by bond angles of 104.5 degrees, with the C-O distances being about 140 pm. The oxygen of the ether is more electronegative than the carbons. Thus, the alpha hydrogens are more acidic than in regular hydrocarbon chains.
Chemical formula: C4H10O
IUPAC name: ethoxyethane.
Health Hazard:
Diethyl ether inhalation may cause headaches, nausea, vomiting and loss of consciousness. If it comes in contact with skin or eyes causes irritation, high exposure to diethyl ether can cause damage to the kidney.
Physical Properties of diethyl ether:
1. Diethyl ether is a colorless, highly volatile liquid. It boils at 308 K. It is lighter than water.
2. It has a pleasant odor and burning taste. Its vapors cause unconsciousness when inhaled.
3. It is slightly soluble in water but readily miscible with alcohol, benzene, etc.
Chemical properties of diethyl ether:
Halogenation: Ether reacts with halogens like chlorine or bromine forming halo substituted ether undergoes substitution reaction in the absence of sunlight.
C2H5OC2H5 + Cl2 → C2H4(Cl)OC2H4(Cl)
Combustion: Ether is a highly flammable liquid and undergoes a combustion reaction resulting in the formation of carbon dioxide and water.
C2H5OC2H5 + 6O2 → 4CO2 + 5H2O.
Water decomposition: water decomposition of the ether occurs when heated with dilute sulfuric acid at high pressure. Water decomposition of diethyl ether yields ethyl alcohol.
C2H5 -O-C2H5 + H2O → 2C2H5OH.
Methods of preparation of diethyl ether:
It is the dominant member of the ether class. It is also called ether or ethyl ether.
Williamson synthesis method: in this method sodium or potassium ethoxide is heated with chloroethane. Bromo ethane or iodo ethane. This reaction results in diethyl ether.
C2H5ONa + C2H5I → C2H5 – O – C2H5 + NaI
By the action of iodoethane and dry silver oxide: Diethyl ether is obtained by heating iodide with dry silver oxide.
By heating a mixture of ethyl alcohol and alumina: Heating ethyl alcohol with alumina (Al2O3) at 250c gives diethyl ether.
C2H5OH + HOC2H5 – Al2O3/250C →C2H5 – O- C2H5 + H20.
Uses of Diethyl ether:
It is used as a solvent and medium in making Grignard reagents and in the Burtz reaction.
Ether has been used in surgery as an anesthetic in combination with chloroform.
By mixing ether in alcohol and used as a fuel in place of petrol like Power alcohol.
It is also used as a refrigerant.
The major use of ether is as a solvent. It easily dissolves many organic substances like oils, fats, and resins. It is largely used as solvents for oils, fats, gums, resins, plastics, etc.
It is used as a refrigerant.
It is used as a general anesthetic in surgery.
Mixed with alcohol, it is used as a substitute for petrol under the name Natalie.
Conclusion:
Significantly, diethyl ether allowed surgeons to perform painful operations on patients rendered unconscious. However, diethyl ether is very flammable, especially in the presence of enriched oxygen mixtures. Due to this, there have been many fires and even explosions in operating rooms during surgery. This is the most important reason why diethyl ether was replaced as a general anesthetic, though it is still used commonly as a solvent and reagent in organic chemistry laboratories. Originally, non-flammable halogenated hydrocarbons like chloroform replaced diethyl ether, but they were more toxic.
