Home
Class 12
CHEMISTRY
Ethers can be prepared by Williamson syn...

Ethers can be prepared by Williamson synthesis which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether can't be prepared by this method. Explain.

Text Solution

Verified by Experts

In order to prepare di-tert butyl ether, sodium tert-butoxide must be reacted with tert-butyl bromide. Alkoxides are not only nucleophiles but they are strong base as well. They react with `3^(@)` alkyl halides leading to the elimination reaction.
When tert-butyl-bromide reacts with sodium tert-butoxide instead of substitution, elimination takes place. As a result of this elimination reaction, Iso butylene is formed instead of di-tert butyl ether.
`{:(" "CH_(2)-H" "CH_(3)" "CH_(2)" "CH_(3)) ,(" |"" |"" ||"" |" ),(H_(3)C-C-Br+Na-O-C-CH_(3) overset("Elimination")rarr H_(3)C-C-CH_(3)+H_(3)C-C-OH+NaBr),(" |"" |" " Iso-butylene" " |" ),(" "CH_(3)" "CH_(3)" "CH_(3) ),("Tert-butyl bromide Sodium.tert butoxide 2-methylpropan-2-ol"):}`
`{:(" "CH_(2)-H" "CH_(3)) ,(" |"" |" ),(H_(3)C-C-Br+Na-O-C-CH_(3) overset("Substitution")rarr "No reaction"),(" |"" |" ),(" "CH_(3)" "CH_(3) ),("Tert-butyl bromide Sodium.tert butoxide"):}`
Promotional Banner

Topper's Solved these Questions

  • ALDEHYDE, KETONES AND CARBOXYLIC ACIDS

    NCERT EXEMPLAR ENGLISH|Exercise Long Answer Type Questions|4 Videos

Similar Questions

Explore conceptually related problems

Ethers can not be prepared by :

Which of the following can not be prepared by Williamson's synthesis ?

Alkyl halides react with metallic sodium in dry ether producing

Identity the following compounds : Saturated ether with fewest C atom atoms (I) that cannot be prepared by Williamson's synthesis. Unsaturated ether with fewest C atoms (II) that cannot be prepared by Williamson's synthesis.

Name the pair of alkyl halide and alkoxide for the preparation of ethyl tert-butyl ether.

Higher homologous of ethers can be prepared from :

Assertion : Aromatic primary amines can be prepared by Gabriel phthalimide synthesis . Reason : Aryl halides undergo uncelophilic substitution with the anion formed by phthalimide .

A : Diphenyl ether is prepared by Williamson synthesis . R : This reaction generally proceed by S_(N)1 mechanism .

Assertion : Ethers can be dried by using sodium wire. Reason : Ethers do not react with sodium.

Assertion(A): Aromatic 1^(@ amines can be prepared by Gabriel phtalmide synthesis. Reason (R ): Aryl halides undergo nucleophilic substitution with anion formed by pthalimide.

NCERT EXEMPLAR ENGLISH-ALCOHOLS, PHENOLS AND ETHERS-All Questions
  1. In Kolbe's reactio insteaded of phenol, phenoxide ion is treated with ...

    Text Solution

    |

  2. Dipole moment of phenol is smaller than that of methanol. Why ?

    Text Solution

    |

  3. Ethers can be prepared by Williamson synthesis which an alkyl halide i...

    Text Solution

    |

  4. Why is the C-O-H bond angle in alcohols slightly less than the tetrahe...

    Text Solution

    |

  5. Explain why low molecular mass alcohols are soluble in water ?

    Text Solution

    |

  6. Explain why p-nitrophenol is more acidic than phenol ?

    Text Solution

    |

  7. Explain why alcohols and ethers of comparable molecular mass have diff...

    Text Solution

    |

  8. The carbon-oxygen bond in phenol is slightly stronger than that in met...

    Text Solution

    |

  9. Arrange water, ethanol and phenol in increasing order of acidity and g...

    Text Solution

    |

  10. Match the structures of the compounds given in Column I with the name ...

    Text Solution

    |

  11. Match the starting material given in Column I with the products formed...

    Text Solution

    |

  12. Match the items of Column I with items of Column II.

    Text Solution

    |

  13. Match the items of Column I with items of Column II.

    Text Solution

    |

  14. Assertion (A) Addition reaction of water to but-1-ene in acidic medium...

    Text Solution

    |

  15. Assertion (A) p-nitrophenol is more acidic than phenol. Reason (R) N...

    Text Solution

    |

  16. Assertion (A) IUPAC name of the compound CH(3)-underset(CH(3))unders...

    Text Solution

    |

  17. Assertion (A) Bond angle is ethers is slightly less than tetrahedral a...

    Text Solution

    |

  18. Assertion (A) Boiling points of alcohols and ethers are high. Reason...

    Text Solution

    |

  19. Assertion (A) Like bromination of benzene, bromination of phenol is al...

    Text Solution

    |

  20. Assertion (A) o-nitrophenol is less soluble in water than the m and p-...

    Text Solution

    |