Question

Write the metamers of diethyl ether. What is its IUPAC name?

Answer 1

Hint: In organic chemistry, metamers are the compounds having the same molecular formula but a different number of carbon atoms (alkyl groups) on either side of the functional group. The phenomenon of being metamers of each other is known as metamerism.

Complete Step by step answer:

-In other words, the isomers in which the alkyl groups are attached to the –O– linkage are different and are known as metamers.

-Metamerism is the chemical property of having the same proportion of atomic components in different arrangements.

-Diethyl ether is a common laboratory colorless, highly volatile, sweet-smelling, aprotic solvent. The chemical formula of diethyl ether is ${{({{C}_{2}}{{H}_{5}})}_{2}}O$.

-There are two metamers of diethyl ether which are-
(i) ${{C}_{2}}{{H}_{5}}-O-{{C}_{2}}{{H}_{5}}$ which have the IUPAC name as Ethoxy ethane.
(ii) $C{{H}_{3}}-C{{H}_{2}}-C{{H}_{2}}-O-C{{H}_{3}}$ which have the IUPAC name as 1-methoxy propane.


Note: Diethyl ethers are mostly produced as a by-product of the vapor-phase hydration of ethylene making ethanol. It can also be synthesized both in laboratories and in industries by acid ether synthesis.
$C{{H}_{3}}C{{H}_{2}}OH+{{H}_{3}}{{O}^{+}}\to C{{H}_{3}}C{{H}_{2}}O{{H}_{2}}^{+}+{{H}_{2}}O$
$C{{H}_{3}}C{{H}_{2}}O{{H}_{2}}^{+}+C{{H}_{3}}C{{H}_{2}}OH\to {{H}_{2}}O+{{H}^{+}}+C{{H}_{3}}C{{H}_{2}}OC{{H}_{2}}C{{H}_{3}}$

-Diethyl ether has various uses and particularly as a solvent in the production of cellulose plastics such as cellulose acetate.

- Diethyl ether has a high cetane number (cetane number is an indicator of the combustion speed of diesel fuel and compression needed for ignition) of 85-96, hence is used as a starting fluid in combination with petroleum distillates for gasoline and diesel engines.

-In the laboratory, diethyl being a hard lewis base reacts with a variety of Lewis acids.


- It is an aprotic solvent that has limited solubility in water. This property when coupled with high volatility makes it ideal for use as the non-polar solvent in liquid-liquid extraction.

-Diethyl ether is extremely flammable and may form explosive vapor/air mixtures, hence it must be handled with care and safety while using. Ether being sensitive to light and air tends to form explosive peroxides.