Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. (1) (2) (3) OH OH + trans-1,2-cyclohexanediol (racemic) Submit Answer 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 p Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: OH OH Retry Entire Group OH (a) CH3ONa+, CH3OH (d) H₂SO4, H₂O (b) OsO4, H₂O2 (c) ethylene oxide (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) 9 more group attempts remaining (9) H₂SO4 (anhydrous) (h) NaOH (i) PBr3 (j) Na, NH3 (1) (k) NBS, heat (N-bromosuccinimide) Previou

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Chapter1: Chemical Foundations
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Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol.
(1)
(2)
(3)
OH
OH
trans-1,2-cyclohexanediol
(racemic)
Submit Answer
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:
(c) ethylene oxide
OH
"OH
(a) CH3O Na+, CH, OH (d) H₂SO4, H₂O
(b) OsO4, H₂O2
Retry Entire Group
OH
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromate
(PCC)
+
9 more group attempts remaining
2
(9) H₂SO4 (anhydrous) (j) Na, NH3 (1)
(h) NaOH
(k) NBS, heat
(i) PBr3
(N-bromosuccinimide)
Previous
Next
Transcribed Image Text:Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. (1) (2) (3) OH OH trans-1,2-cyclohexanediol (racemic) Submit Answer 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: (c) ethylene oxide OH "OH (a) CH3O Na+, CH, OH (d) H₂SO4, H₂O (b) OsO4, H₂O2 Retry Entire Group OH (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) + 9 more group attempts remaining 2 (9) H₂SO4 (anhydrous) (j) Na, NH3 (1) (h) NaOH (k) NBS, heat (i) PBr3 (N-bromosuccinimide) Previous Next
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