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Ethers and Epoxides; Thiols and Sulfides - PowerPoint PPT Presentation

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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

Ethers and Epoxides;

Thiols and Sulfides

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

  • Examples:

Diethyl ether

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Methyl phenyl ether (Anisole)

Tetrahydrofuran (cyclic ether)

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Naming of Ethers

There are two ways to name it:

  • Identifying the two organic substituents and adding the word ether

Dimethyl ether

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Tert-Butyl methyl ether

Ethyl-phenyl ether

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Tert-butoxy butane

Para-ethoxy methoxy benzene

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1-methoxy-cyclohexene considered an


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Isopropoxy cyclohexane considered an


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  • Physical Properties considered an

  • Soluble in water

  • Boiling point: very low, about 200C

  • R—O—R bonds: tetrahedral bond angle

  • The Oxygen atom is sp3-hybridized

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Preparation of Ethers considered an

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Symmetrical ethers considered an R-O-R

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Mechanism: considered an

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Examples considered an

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Symmetrical ethers considered an R-O-R’

  • The Williamson Ether Synthesis:

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Examples considered an


Α-D-Glucose pentamethyl ether

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tert-Butoxide ion considered an


tert-Butyl methyl ether

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Methoxide ion considered an



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1) considered an Reaction

  • Alkoxymercuration of Alkenes

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2. considered an Mechanism

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3. considered an Examples



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Reaction of Ethers considered an

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  • Acidic Cleavage considered an

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

Ethyl isopropyl ether

Isopropyl alcohol


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Mechanism considered an

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Examples: considered an


Ethyl phenyl ether


2-Ethoxypropanoic acid


Lactic acid

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

E1 reaction

tert-Butyl cyclohexyl ether



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Mechanism: by an

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S by an N1 reaction

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Mechanism: by an

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1) by an Claisen rearrangement is pecific to allyl aryl ethers, Ar-O-CH2CH=CH2

  • Claisen Rearrangement

2) Example:


Sodium phenoxide

Allyl phenyl ether

Allyl phenyl ether


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3) by an Mechanism:

Transition state