Epoxidesâ€™ physical properties are similar to that of ethers but are chemically much more reactive. Epoxide molecules do not have the capability of forming hydrogen bonds with each other due to the lack of directly bonded H atom with the O atom. Hence, this results in their relatively low boiling points when compared to the corresponding alcohols. As the carbon chains grow, the difference in the boiling points of the ethers and their corresponding alcohols becomes lower due to the domination of increased van der Waals interactions of the elongated C chains, which overpower the presence of hydrogen bonding.
They are slightly polar due to the electronegativity difference between the O and C atoms. The Câ€“Oâ€“C bond angle in the ether functional group is about 110Â° and the Câ€“O bond dipoles do not cancel out each other due to this bond angle.
Epoxides like all other ethers have higher polarity compared to the corresponding alkanes or alkenes but lesser than that of alcohols, esters, amides, and acids of comparable structures. The two lone pairs of electrons on the oxygen atoms facilitate the formation of hydrogen bonds with water molecules. Hence, they have slight solubility in water. This solubility decreases as the R groups elongate.
Epoxides such as tetrahydrofuran and 1,4-dioxane have greater solubility in water compared to their linear counterparts because in them the oxygen atom is more exposed for hydrogen bonding.
Structure and Reactivity of Epoxides:
Structure of epoxides can be described as follows:
The epoxide unit has a three membered ring in which there are two carbon atoms and one O atom.
The atoms are bonded together by covalent bonds, which are highly strained.
Both the C-O bonds are polar due to the high electronegativity difference between the C and O atoms.
The C-O dipole moment is not 0.
Following are the chemical properties of epoxides:
Epoxides are much more reactive than the linear ethers due to high angular strain.
The small ring system having a high ring strain relieves it by opening the ring; thereby making it prone to nucleophilic attack.
Nucleophiles attack the C atom of the C-O bond causing the C-O bond to break, resulting in ring opening.
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