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Organic Chemistry

18.1 Names and Properties of Ethers

Organic Chemistry18.1 Names and Properties of Ethers

18.1 • Names and Properties of Ethers

Simple ethers with no other functional groups are named by identifying the two organic substituents and adding the word ether.

The structure of isopropyl methyl ether and ethyl phenyl ether. Their oxygen bonds with organic groups are highlighted.

If other functional groups are present, the ether part is considered an alkoxy substituent. For example:

The structures of p-dimethoxybenzene and 4-tert-butoxy-1-cyclohexene. The carbon atoms are numbered from the double bond position in 4-tert-butoxy-1-cyclohexene.

Like alcohols, ethers have nearly the same geometry as water. The R–O–R bonds have an approximately tetrahedral bond angle (112° in dimethyl ether), and the oxygen atom is sp3-hybridized.

The orbital picture, space-filling model, and ball-and-stick model in the electrostatic potential map of dimethyl ether. The bond angle between methyl-oxygen-methyl is 112 degrees.

The electronegative oxygen atom gives ethers a slight dipole moment, and the boiling points of ethers are often slightly higher than the boiling points of comparable alkanes. Table 18.1 compares the boiling points of some common ethers and their corresponding hydrocarbons.

Table 18.1 Comparison of Boiling Points of Ethers and Hydrocarbons
Ether Boiling point °C Hydrocarbon Boiling point °C
CH3OCH3 –25  CH3CH2CH3 –45
CH3CH2OCH2CH3  34.6 CH3CH2CH2CH2CH3  36
A five-membered ring, one atom of which is oxygen. 65  The structure of cyclopentane which is a five-membered carbon ring.  49
Structure of benzene with a methoxy (O C H 3) substituent. 158  The structure of benzene with an ethyl (C H 2 C H 3) substituent. 136

Ethers are relatively stable and unreactive in many respects, but some ethers react slowly with the oxygen in air to give peroxides, compounds that contain an O–O bond. The peroxides from low-molecular-weight ethers such as diisopropyl ether and tetrahydrofuran are explosive and extremely dangerous, even in small amounts. Ethers are very useful as solvents in the laboratory, but they must always be used cautiously and should not be stored for long periods of time.

Problem 18-1
Name the following ethers:
The structure of two isopropyl groups bonded to an oxygen atom in an ether linkage.
The structure of cyclopentane with a propoxy (O C H 2 C H 2 C H 3) substituent.
The structure of benzene with methoxy and bromine groups positioned para to one another.
The structure of cyclohexene with a methoxy substituent at one of the double-bonded carbons.
An ethyl group connected to an isobutyl group through an oxygen atom, forming an ether linkage.
An allyl group attached to a vinyl group through an oxygen atom, forming an ether linkage.
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