Ethers & Epoxides ; Thiols & Sulfides

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Last updated 6:07 PM on 9/16/26
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12 Terms

1
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Williamson Synth

Alcohol —> Ether

1) NaH

2) RX

2
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Alkyoxymercuration Demerucuration

Alkene —> Add ether

1) Hg(OAc)2, ROH

2) NaBH4

3
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Acidic Cleavage

Ether —> two alkyl halides

xs HX , heat

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Autooxidation

Ether —> add OOH

O2 (slow)

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Prep Epoxides

MCPBA

or

1) Br2, H2O

2) NaOH

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Ring Opening

Strong Nucs (5)

1) NaOR or NaCN or NaSR or RMgBr or LiAlH4

2) H3O+

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Ring Opening

Acid Catalyzed (3)

  • HX

  • H2SO4 , H2O

  • H2SO4 , ROH


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Thiols

Alkyl Halide —> Thiol

NaSH

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Thiols

Two Alkyl SH —> S-S

NaOH , H2O

Br2


Opposite:

HCl, Zn

10
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Sulfides

Alkyl SH —> Sulfide

1) NaOH

2) RX

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Sulfides

Sulfide —> Sulfoxide

NaIO4

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Sulfides

Sulfide —> Double sulfoxide

H2O2