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Ethers

Ethers. Unit 7. Ethers!. Ether – organic compounds where two alkyl or aryl groups joined singly with an oxygen atom R-O-R’ R-O-Ar Ar-O-Ar. Ethers. Symmetrical ethers – 2 identical groups bonded to the oxygen Unsymmetrical ethers – two different groups bonded to the oxygen.

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Ethers

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  1. Ethers Unit 7

  2. Ethers! Ether – organic compounds where two alkyl or aryl groups joined singly with an oxygen atom R-O-R’ R-O-Ar Ar-O-Ar

  3. Ethers Symmetrical ethers – 2 identical groups bonded to the oxygen Unsymmetrical ethers – two different groups bonded to the oxygen

  4. Nomenclature Name the attached groups followed by ether C-O-C-C Methyl ethyl ether (unsymm) C-C-O-C-C Diethyl ether (symm) C-C-O- C-C-C-C-O-

  5. Preparation of Ethers • Symmetrical ethers = dehydrate alcohols 2R-OH H2SO4 R-O-R + H2O Form dipropyl ether 2 C-C-C-OH H2SO4 C-C-C-O-C-C-C + H2O 2CH3CH2CH2OH H2SO4 CH3(CH2)2O(CH2)2CH3 + H2O

  6. Preparation of Ethers 2. Unsymmetrical ethers = Williamson Synthesis Alkyl halide + alcohol salt  ether + metal halide RX + RO-M+  ROR’ + MX

  7. Preparation of Ethers - Williamson • If there are 2 alkyl groups, the smaller alkyl group is the halide and the larger is the metal salt • If there is an alkyl group and a phenyl, the phenyl is ALWAYS the salt 

  8. Preparation of Ethers - Williamson • Form methyl ethyl ether (name reactants) CH3Cl + (C-C-O-)Na+ C-O-C-C + NaCl CH3Cl+(CH3CH2O-)Na+  CH3OCH2CH3+NaCl Methyl chloride + sodium ethoxide (chlormethane)

  9. Preparation of Ethers - Williamson • Form propyl phenyl ether

  10. Reactions of Ethers • Ether + hydrogen halide  alcohol + alkyl halide • ROR + HX  ROH + RX • If either had two alkyl groups, the smaller one forms the alcohol. If it is a phenyl and an alcohol, the phenyl forms phenol

  11. Reactions of Ethers • React ethyl phenyl ether w/HBr • C-C-O- + HBr C-C-Br + -OH • React methy phenyl ether w/HF

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