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Which of the following cannot be made by using Williamson's synthesis?
  • a)
    Methoxybenzene
  • b)
    Benzyl p-nitrophenyl ether
  • c)
    Methyl tert-butyl ether
  • d)
    Di-tert-butyl ether
Correct answer is option 'D'. Can you explain this answer?
Most Upvoted Answer
Which of the following cannot be made by using Williamsons synthesis?a...
Di tert butyl ether cannot be prepared by William son's synthesis
If it should be prepared, we have to react tert butyl bromide and sodium tert butoxide.
If we do so, since the halide being tertiary, basic character will become predominant and alkane will be formed.
Thus, Di tert butyl ether cannot be prepared by William son's synthesis
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Community Answer
Which of the following cannot be made by using Williamsons synthesis?a...
Di-tert-butyl ether cannot be made using Williamsons synthesis.
Williamson synthesis is a method used for the preparation of ethers from alkyl halides and alkoxides. However, di-tert-butyl ether cannot be synthesized using this method due to the following reasons:
- Steric hindrance: Di-tert-butyl ether has bulky tert-butyl groups on both sides of the oxygen atom. The high degree of steric hindrance makes it difficult for the alkoxide ion to attack the alkyl halide and form the ether product.
- Reactivity of tert-butyl halides: Tert-butyl halides are less reactive compared to primary or secondary alkyl halides. The low reactivity of tert-butyl halides makes it challenging to carry out the Williamson synthesis to form di-tert-butyl ether.
- Side reactions: In the case of di-tert-butyl ether synthesis using Williamson synthesis, there is a high chance of side reactions due to the presence of bulky tert-butyl groups. These side reactions can lead to the formation of undesired by-products instead of the desired ether product.
Therefore, due to the steric hindrance, low reactivity of tert-butyl halides, and the possibility of side reactions, di-tert-butyl ether cannot be efficiently prepared using Williamson synthesis.
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Which of the following cannot be made by using Williamsons synthesis?a)Methoxybenzeneb)Benzyl p-nitrophenyl etherc)Methyl tert-butyl etherd)Di-tert-butyl etherCorrect answer is option 'D'. Can you explain this answer?
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