What is the Difference Between Anisole and Diethyl Ether?

Anisole and diethyl ether are two different types of ethers, which are organic compounds that feature a C–O–C linkage. Here are the main differences between them:

1. Structure: Anisole, also known as methoxybenzene, has a benzene ring with a methoxy group attached to it, while diethyl ether only has ethyl groups connected to the oxygen atom.
2. Flammability: Anisole is moderately flammable, whereas diethyl ether is extremely flammable.
3. Density of vapor: Diethyl ether is a colorless liquid at room temperature, and its vapor is more dense than air. Anisole, on the other hand, has a vapor density slightly higher than air and is slightly soluble in water.
4. Boiling point: Anisole has a lower boiling point than diethyl ether.
5. Solubility in water: Unlike diethyl ether, anisole is only slightly soluble in water.
6. Smell: Diethyl ether has a strong, somewhat sweet odor, and its vapor can cause drowsiness or unconsciousness. Anisole, on the other hand, has a much weaker odor.
7. Historical use: Diethyl ether was once commonly used as a general anesthetic, while anisole does not have the same historical context.

Comparative Table: Anisole vs Diethyl Ether

Here is a table comparing the differences between anisole and diethyl ether:

Anisole is a mixed ether, with one ether carbon being part of a methyl group and the other being part of a benzene ring. In contrast, diethyl ether is a symmetrical, saturated ether with C-O-C bond angles of 111° and C-O distances of 141 pm. The C-O bonding in anisole is asymmetric, meaning the two C-O bonds are chemically different and have different force constants. On the other hand, the C-O bonding in diethyl ether is symmetric.