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A student wanted to use the Williamson ether synthesis to
Chapter 3, Problem 35SP(choose chapter or problem)
Problem 35SP
A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an 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 madeethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.
(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the sN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.
(b) What would have been the best synthesis of (R)-2-ethoxybutane?
(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?
Questions & Answers
QUESTION:
Problem 35SP
A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an 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 madeethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.
(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the sN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.
(b) What would have been the best synthesis of (R)-2-ethoxybutane?
(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?
ANSWER: