John E. McMurry
www.cengage.com/chemistry/mcmurry
Chapter 18
Ethers and Epoxides; Thiols and
Sulfides
Paul D. Adams • University of Arkansas
, Ethers and Their Relatives
▪ An ether has two organic groups (alkyl, aryl, or vinyl) bonded to the
same oxygen atom, R–O–R
▪ Diethyl ether is used industrially as a solvent
▪ Tetrahydrofuran (THF) is a solvent that is a cyclic ether
▪ Thiols (R–S–H) and sulfides (R–S–R) are sulfur (for oxygen)
analogues of alcohols and ethers
,Why this Chapter?
▪ To finish covering functional groups with C-O
and C-S single bonds
▪ Focus on ethers and look at thiols and sulfides
before going on to C=O
, 18.1 Names and Properties of
Ethers
▪ Simple ethers are named by identifying the two organic
substituents and adding the word ether
▪ If other functional groups are present, the ether part is
considered an alkoxy substituent
▪ R–O–R ~ tetrahedral bond angle (112° in dimethyl ether)
▪ Oxygen is sp3-hybridized
▪ Oxygen atom gives ethers a slight dipole moment
www.cengage.com/chemistry/mcmurry
Chapter 18
Ethers and Epoxides; Thiols and
Sulfides
Paul D. Adams • University of Arkansas
, Ethers and Their Relatives
▪ An ether has two organic groups (alkyl, aryl, or vinyl) bonded to the
same oxygen atom, R–O–R
▪ Diethyl ether is used industrially as a solvent
▪ Tetrahydrofuran (THF) is a solvent that is a cyclic ether
▪ Thiols (R–S–H) and sulfides (R–S–R) are sulfur (for oxygen)
analogues of alcohols and ethers
,Why this Chapter?
▪ To finish covering functional groups with C-O
and C-S single bonds
▪ Focus on ethers and look at thiols and sulfides
before going on to C=O
, 18.1 Names and Properties of
Ethers
▪ Simple ethers are named by identifying the two organic
substituents and adding the word ether
▪ If other functional groups are present, the ether part is
considered an alkoxy substituent
▪ R–O–R ~ tetrahedral bond angle (112° in dimethyl ether)
▪ Oxygen is sp3-hybridized
▪ Oxygen atom gives ethers a slight dipole moment
