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 CO K+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 (c) ethylene oxide OH (9) H₂SO4 (anhydrous)) Na, NH3 (1) (h) NaOH (k) NBS, heat (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate PBr3 (PCC) (N-bromosuccinimide) Previous Next

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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
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
(c) ethylene oxide
(a) (CH3)3CO¯K+, THF (d) H₂SO4, H₂O
(b) OsO4, H₂O2
Br
OH
+
(9) H₂ SO4 (anhydrous) Na, NH3 (1)
(k) NBS, heat
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromate) PBr3
(PCC)
(h) NaOH
(N-bromosuccinimide)
Previous
Next
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 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 (c) ethylene oxide (a) (CH3)3CO¯K+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 Br OH + (9) H₂ SO4 (anhydrous) Na, NH3 (1) (k) NBS, heat (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate) PBr3 (PCC) (h) NaOH (N-bromosuccinimide) Previous Next
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