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In Williamson ether synthesis conjugate acid of corresponding alkoxide ion is taken as solvent instead of any other alcohol. Why it is like that?

User KimHee
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Final answer:

In Williamson ether synthesis, using the conjugate acid of the alkoxide ion as the solvent ensures that side reactions are minimized, as ethers are less reactive than alcohols. The use of the alkoxide's conjugate acid creates suitable conditions for the reaction to proceed towards ether formation and not side products.

Step-by-step explanation:

In Williamson ether synthesis, the conjugate acid of the corresponding alkoxide ion is used as the solvent to avoid the potential side reactions that other alcohols might introduce. Ethers are generally less reactive than alcohols; they lack an acidic hydrogen which makes ethers useful as inert solvents in various chemical reactions. When dealing with the synthesis of ethers via the Williamson approach, using the conjugate acid of the alkoxide ion as the solvent ensures consistency in the reaction media and reduces the probability of the alkoxide reacting with other alcohol molecules, which would instead lead to unwanted by-products or side reactions.

In elimination reactions, where the synthesis of alkenes is intended from alcohols through dehydration, the choice of solvent can significantly affect the outcome of the reaction. Sulfuric acid is often used to protonate the alcohol, turning it into a good leaving group. Its conjugate base, HSO4-, is a weak nucleophile, preventing substitution reactions and favoring elimination to form the alkene. Excess alcohol or the removal of water can drive the reaction forward, but using the conjugate acid as the solvent helps in maintaining the reaction condition conducive for ether formation.

User Nimesh Vaghasiya
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