Textbook Question
Design a synthesis for each of the following, using an intramolecular reaction:
a.
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12. Alcohols, Ethers, Epoxides and Thiols
Williamson Ether Synthesis
Multiple Choice
Which of the following statements about the ether synthesis is correct regarding the preparation of unsymmetrical ethers?
A
Only symmetrical ethers can be formed by the ether synthesis.
B
The ether synthesis is only suitable for preparing aromatic ethers.
C
Unsymmetrical ethers can be prepared by reacting a primary alkyl halide with an alkoxide ion derived from a different alcohol.
D
Unsymmetrical ethers cannot be synthesized using the ether synthesis.
Verified step by step guidance1
Recall that the Williamson ether synthesis involves the reaction of an alkoxide ion (RO\(\textsuperscript{-}\)) with an alkyl halide (R'X) to form an ether (ROR').
Understand that the alkoxide ion is typically prepared by deprotonating an alcohol (ROH) with a strong base, generating a nucleophile.
Recognize that the alkyl halide acts as the electrophile, and the reaction proceeds via an S\(\textsubscript{N}\)2 mechanism, favoring primary alkyl halides to avoid elimination or rearrangement.
Note that unsymmetrical ethers can be synthesized by choosing different alkoxide ions and alkyl halides, for example, reacting a primary alkyl halide with an alkoxide derived from a different alcohol.
Conclude that the Williamson ether synthesis is versatile and not limited to symmetrical ethers or aromatic ethers; it is especially effective for preparing unsymmetrical ethers when the alkyl halide is primary.
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