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Chapter 18. Ethers and Epoxides; Thiols and Sulfides. Ethers. Definition: Two organic groups bonded to the same oxygen atom Examples:. Diethyl ether. Methyl phenyl ether (Anisole). Tetrahydrofuran (cyclic ether). Naming of Ethers. There are two ways to name it:

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chapter 18

Chapter 18

Ethers and Epoxides;

Thiols and Sulfides

ethers
Ethers
  • Definition: Two organic groups bonded to the same oxygen atom
  • Examples:

Diethyl ether

slide3
Methyl phenyl ether (Anisole)

Tetrahydrofuran (cyclic ether)

naming of ethers
Naming of Ethers

There are two ways to name it:

  • Identifying the two organic substituents and adding the word ether

Dimethyl ether

slide5
Tert-Butyl methyl ether

Ethyl-phenyl ether

slide6
If other functional groups are present, the ether part is considered an alkoxy substituent.

Tert-butoxy butane

Para-ethoxy methoxy benzene

slide7
1-methoxy-cyclohexene

4-tert-Butoxy-1-cyclohexene

slide8
Isopropoxy cyclohexane

p-dimethoxybenzene

slide9
Physical Properties
  • Soluble in water
  • Boiling point: very low, about 200C
  • R—O—R bonds: tetrahedral bond angle
  • The Oxygen atom is sp3-hybridized
symmetrical ethers r o r14
Symmetrical ethersR-O-R’
  • The Williamson Ether Synthesis:
examples15
Examples

α-D-Glucose

Α-D-Glucose pentamethyl ether

slide16
tert-Butoxide ion

Iodomethane

tert-Butyl methyl ether

slide17
Methoxide ion

2-Chloro-2-methylpropane

2-Methylpropene

slide18
1) Reaction
  • Alkoxymercuration of Alkenes
slide20
3. Examples

Styrene

1-Methoxy-1-phenyethane

slide22
Acidic Cleavage

1) Ethers with primary and secondary alkyl groups react by an SN2

Ethyl isopropyl ether

Isopropyl alcohol

Iodoethane

slide24
Examples:

Bromoethane

Ethyl phenyl ether

Phenol

2-Ethoxypropanoic acid

Iodoethane

Lactic acid

slide25
2) Ethers with a tertiary, benzylic, or allylic group react by an SN1 or E1

E1 reaction

tert-Butyl cyclohexyl ether

Cyclohexanol

2-Methylpropene

slide29
1) Claisen rearrangement is pecific to allyl aryl ethers, Ar-O-CH2CH=CH2
  • Claisen Rearrangement

2) Example:

Phenol

Sodium phenoxide

Allyl phenyl ether

Allyl phenyl ether

0-Allylphenol

slide30
3) Mechanism:

Transition state

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