A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2 goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane. What would have been the best synthesis of (R)-2-ethoxybutane?
A student wanted to use the
Ethers are the organic molecules with the functional groups RORI.
Where, R and RI are alkyl groups.
Williamson ether synthesis involves the reaction between alkoxide ion (which acts as a nucleophile) and alkyl halide/alkyl tosylate (acts as an electrophile).
The reaction takes place with SN2 mechanism and inversion of configuration takes place.
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