Select all the syntheses that produce the pictured ether in better than 50% yield: 2-butanol treated with sodium hydride followed by methyl chloride a 50/50 mixture of methanol and 2-butanol heated with concentrated sulfuric acid methanol treated with sodium hydride followed by 2-chlorobutane O 2-butanol treated with sodium hydride followed by chloroethane

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.46P: Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic...
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Select all the syntheses that produce the pictured ether in better than 50% yield:
2-butanol treated with sodium hydride followed by methyl chloride
a 50/50 mixture of methanol and 2-butanol heated with concentrated sulfuric acid
methanol treated with sodium hydride followed by 2-chlorobutane
O 2-butanol treated with sodium hydride followed by chloroethane
Transcribed Image Text:Select all the syntheses that produce the pictured ether in better than 50% yield: 2-butanol treated with sodium hydride followed by methyl chloride a 50/50 mixture of methanol and 2-butanol heated with concentrated sulfuric acid methanol treated with sodium hydride followed by 2-chlorobutane O 2-butanol treated with sodium hydride followed by chloroethane
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