Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (1) (2) (3) OH (4) 2-ethoxy-1-butanol (racemic) OH Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: OH Br (a) (CH3)3 COK, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 (c) ethylene oxide OH (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) (9) H₂SO4 (anhydrous) (j) Na, NH3 (1) (h) NaOH (k) NBS, heat (i) PBr3 (N-bromosuccinimide) Previous Next

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
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.76P: Using your reaction roadmaps as a guide, show how to convert ethanol, formaldehyde, and acetone into...
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Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of
all carbon atoms in the ether product.
(1)
(2)
(3)
OH
(4)
2-ethoxy-1-butanol
(racemic)
OH
OH
(c) ethylene oxide
Suggest reagents and experimental conditions for each step in this synthesis.
From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible.
Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown.
Reagents:
(a) (CH3)3 COK+, THF (d) H₂SO4, H₂O
(b) OsO4, H₂O2
Br
OH
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromate
(PCC)
+
2
Oly
(i) PBr3
(9) H₂SO4 (anhydrous)
(h) NaOH
(j) Na, NH3 (1)
(k) NBS, heat
(N-bromosuccinimide)
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Transcribed Image Text:Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (1) (2) (3) OH (4) 2-ethoxy-1-butanol (racemic) OH OH (c) ethylene oxide Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: (a) (CH3)3 COK+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 Br OH (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) + 2 Oly (i) PBr3 (9) H₂SO4 (anhydrous) (h) NaOH (j) Na, NH3 (1) (k) NBS, heat (N-bromosuccinimide) Previous Next Save and Exit ?
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