ethers epoxides n.
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Ethers & Epoxides. Ether Nomenclature. Compounds that contain two organic groups attached to an oxygen atom General formula is 1. Common Names Name both groups attached to the oxygen in alphabetical order Add the word ether. Ether Nomenclature Examples. 1. 2. 3. 4. 5.

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ether nomenclature
Ether Nomenclature
  • Compounds that contain two organic groups attached to an oxygen atom
  • General formula is
  • 1. Common Names
    • Name both groups attached to the oxygen in alphabetical order
    • Add the word ether
slide4

4.

  • 5.
slide5

2. IUPAC Names

  • In the IUPAC system, ethers are named as alkoxy substituents
  • Ex.:

CH3—CH—CH2—CH2—CH3

O—CH3

epoxide nomenclature
Epoxide Nomenclature
  • Also known as oxiranes
  • Three-membered, saturated cyclic ring with one oxygen atom
  • Much more reactive than ordinary ethers (due to the abnormally small bond angles)
  • General formula
slide7

1. Common names

    • Number the alkyl chain indicating the two carbons to which the oxygen is attached
    • Use the prefix epoxy-
    • Ex. 1
    • Ex.2.
slide8

Ex. 3.

  • 2. IUPAC Names
    • Number the ring with oxygen as #1
    • Use the ending oxirane

Ex. 1

reactions of ethers
Reactions of Ethers
  • Ethers are relatively stable, especially to dilute acids or alkalis & many oxidizing & reducing agents
  • Do not react with sodium (this property distinguishes them from alcohols)
  • Are weak bases which dissolve in concentrated sulfuric acid (this property distinguishes them from saturated hydrocarbons)
  • React with oxygen in the air to form dangerous explosive peroxides
preparation of ethers
Preparation of Ethers
  • 1. Intermolecular Dehydration of Alcohols
  • Used to make symmetrical ethers
  • Reagent is H2SO4 at 140°C
  • Ex. Dehydrate two moles of ethanol
  • Ex. Dehydrate tertbutanol
slide12

2. Williamson Synthesis

  • Reaction of an alkyl halide with an alcohol (or an alkoxide ion)
  • Can be used to make either symmetrical or unsymmetrical ethers
  • The alkyl halide must be primary or secondary
  • Ex. React methanol with ethyl chloride.
slide13

Alkyl sulfates, in the presence of NaOH, are used to prepare ethers of phenols

  • Ex. React phenol with dimethylsulfate
preparation of epoxides
Preparation of Epoxides
  • 1. Oxidation of Ethylene
  • Uses silver as the catalyst at 250°C
  • Ex:
  • 2. Intramolecular Williamson Synthesis
  • Uses hypochloric acid (HClO) and hydroxide
  • Ex:
reactions of epoxides
Reactions of Epoxides
  • the three membered ring is highly strained and opens easily
  • 1. Acid Catalyzed Addition
    • A. Hydrolysis of epoxyethane
      • Uses dilute acid; used to make trans diols
      • Ex.; Hydrolyze 1,2-epoxycyclohexane with dilute acid
    • B. Treatment with concentrated acid

Ex. React oxirane with concentrated HCl.

slide16

C. In alcoholic solutions

  • Ex. React oxirane with methanol
  • D. with ethylene glycol
  • Ex. React oxirane with ethylene glycol
slide17

2. Base Catalyzed Addition

      • Uses ammonia
  • 3. Reaction with a Grignard Reagent
      • Extends the chain of the Grignard reagent by two carbons
      • Product is a primary alcohol
      • Ex. React oxirane with phenylmagnesium bromide