Book Cover Organic Chemistry 4e Carey
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Chapter 16: Ethers, Epoxides and Sulfides



Summary | Ethers | Preparations of Ethers | Reactions of Ethers | Epoxides | Preparation of Epoxides | Reactions of Epoxides | Spectroscopic Analysis of Ethers | Sulfides | Self Assessment | Quiz |


Ethers

Chapter 16: Ethers, Epoxides and Sulfides

 

dimethyl ether
methoxymethane
 diethyl ether
ethoxyethane
t-butyl methyl ether
(MTBE)
tetrahydrofuran
(THF)
(common solvent)
(fuel additive)
(common solvent)

Questions :
What do you think the acronym MTBE stands for ? methyl t-butyl ether
Is this an alternative correct IUPAC name the fuel additive ? No, the alkyl groups should be listed in alphabetical order, ignoring t-

Physical Properties:

Structure:
diethyl ether
 pentane
tetrahydropyran
cyclohexane

Questions :
What type of conformation is diethyl ether shown in the CHIME image above ?staggered, all anti
What type of conformation is tetrahydropyran shown in the CHIME image above ?a chair like cyclohexane

Reactivity:

electrostatic potential of dimethyl ether The image shows the electrostatic potential for dimethyl ether. 
The more red an area is, the higher the electron density and the more blue an area is, the lower the electron density.
  • The ethereal O atom is a region of high electron density (red) due to the lone pairs.
  • Ether oxygen atoms are Lewis bases.
  • Like an alcohol -OH group, the -OR group is a poor leaving group and needs to be converted to a better leaving group before substitution can occur.
  • The most important reaction of ethers is their cleavage by strong acids such as HI or HBr.



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