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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?
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Most Upvoted Answer
Which of the following cannot be made by using Williamsons synthesis?a...
Williamson's synthesis is a method used for the preparation of ethers by reacting alkyl halide or aryl halide with alkoxide or aryl oxide in the presence of a strong base. The reaction involves the nucleophilic substitution of halide ion by alkoxide ion or aryl oxide ion. This method is commonly used for the preparation of symmetrical ethers.
Explanation:
Di-tert-butyl ether is a compound that cannot be prepared using Williamson's synthesis. This is because the synthesis involves the use of a strong base, which can cause the tert-butyl group to undergo elimination instead of substitution. The elimination reaction leads to the formation of alkenes instead of ethers.
The reaction for the preparation of ethers using Williamson's synthesis is as follows:
R-X + R'O(-) --> R-O-R' + X(-)
where R represents an alkyl or aryl group, X represents a halide ion, and R' represents an alkyl or aryl oxide ion.
In the case of di-tert-butyl ether, the reaction would be:
(t-BuO)2 + (t-BuBr) --> t-Bu-CH=CH-t-Bu + Br(-)
The tert-butyl group undergoes elimination to form an alkene instead of the desired ether.
In summary, while Williamson's synthesis is a useful method for the preparation of ethers, it cannot be used for the synthesis of di-tert-butyl ether due to the tendency of the tert-butyl group to undergo elimination.
Explanation:
Di-tert-butyl ether is a compound that cannot be prepared using Williamson's synthesis. This is because the synthesis involves the use of a strong base, which can cause the tert-butyl group to undergo elimination instead of substitution. The elimination reaction leads to the formation of alkenes instead of ethers.
The reaction for the preparation of ethers using Williamson's synthesis is as follows:
R-X + R'O(-) --> R-O-R' + X(-)
where R represents an alkyl or aryl group, X represents a halide ion, and R' represents an alkyl or aryl oxide ion.
In the case of di-tert-butyl ether, the reaction would be:
(t-BuO)2 + (t-BuBr) --> t-Bu-CH=CH-t-Bu + Br(-)
The tert-butyl group undergoes elimination to form an alkene instead of the desired ether.
In summary, while Williamson's synthesis is a useful method for the preparation of ethers, it cannot be used for the synthesis of di-tert-butyl ether due to the tendency of the tert-butyl group to undergo elimination.
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Community Answer
Which of the following cannot be made by using Williamsons synthesis?a...
To prepare di-tert butyl ether, a tertiary-butyl halide is required. However, Williamson synthesis does not occur with tertiary halides because with tertiary halides, reaction undergoes elimination to form alkene rather than substitution reaction. So, option d is correct.
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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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