What is the Difference Between Ethyl Nitrite and Nitroethane?

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Ethyl nitrite and nitroethane are two chemical compounds with the same chemical formula, C2H5NO2, but they have different chemical structures, making them functional isomers. The key difference between the two is the arrangement of the oxygen atoms in relation to the carbon and nitrogen atoms:

  • In ethyl nitrite, one oxygen atom is attached to a carbon atom, and the other oxygen atom is attached to a nitrogen atom.
  • In nitroethane, both oxygen atoms are bonded to the nitrogen atom.

Some additional differences between ethyl nitrite and nitroethane include:

  1. Hydrolysis: Ethyl nitrite undergoes hydrolysis, forming C2H5OH, while nitroethane does not undergo hydrolysis.
  2. Boiling point: Ethyl nitrite has a low boiling point of 17°C, while nitroethane has a much higher boiling point of 115°C.
  3. Reduction with metal and acid: Ethyl nitrite can be reduced with a mixture of tin and hydrochloric acid (Sn/HCl) or with LiAlH4, but nitroethane does not react in this manner.
  4. Reactivity with nitrous acid: Ethyl nitrite reacts with nitrous acid to form a pseudo-nitrol, which dissolves in alkali to give a blue solution. Tertiary nitro alkanes do not react with nitrous acid.

Comparative Table: Ethyl Nitrite vs Nitroethane

Ethyl nitrite and nitroethane are two chemical compounds with the same chemical formula, C2H5NO2, but they have different structures and properties. Here is a table comparing the differences between the two:

Property Ethyl Nitrite Nitroethane
Chemical Structure One oxygen atom attached to a carbon atom and one oxygen atom attached to a nitrogen atom Both oxygen atoms bonded to the nitrogen atom
Preparation Can be prepared from ethanol Produced industrially by treating propane with nitric acid or via the Victor Meyer reaction of haloethanes with silver nitrite
Physical Properties Poorly soluble in water, molar mass of 75.067 g/mol, boiling point of 17°C Oily liquid at standard temperature and pressure, colorless with a fruity odor
Hydrolysis Forms C2H5OH on hydrolysis Does not undergo hydrolysis

Ethyl nitrite is a type of alkyl nitrite and can be used as a reagent with butanone to yield dimethylglyoxime as the end product. Nitroethane is used as a fuel additive, a precursor to rocket propellants, and as a solvent for polymers such as polystyrene.