Multiple Choice
Which of the following ethers cannot be prepared by the Williamson ether synthesis?
12. Alcohols, Ethers, Epoxides and Thiols
Williamson Ether Synthesis
Multiple Choice
Which synthesis would be best to make the following target?
A
B
C
D
Verified step by step guidance1
Identify the target molecule as an ether with a chiral center, specifically an ethyl group attached to an oxygen, which is connected to a chiral carbon with two methyl groups and an isopropyl group.
Consider the synthesis options provided. The first option involves an alkene and an alcohol with sulfuric acid, which typically leads to ether formation via an acid-catalyzed dehydration reaction.
The second option involves an alkene and ethanol with sulfuric acid, which can also form ethers through an acid-catalyzed reaction, but the stereochemistry might not be controlled.
The third option involves a chiral alcohol reacting with sodium hydride (NaH) followed by ethyl bromide (EtBr). This is a Williamson ether synthesis, which is a good method for forming ethers with controlled stereochemistry.
The fourth option involves ethanol reacting with a chiral alcohol using NaH. This is another Williamson ether synthesis, but the roles of the alcohols are reversed, which might not lead to the desired ether with the correct stereochemistry.
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