Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. OH OH + trans-1,2-cyclohexanediol (racemic) OH "OH 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: (a) CH3O Na+, CH3OH (d) H₂SO4, H₂O (b) OsO4, H₂O2 (c) ethylene oxide (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) O (9) H₂SO4 (anhydrous) (h) NaOH (i) PBr3 (j) Na, NH3 (1) (k) NBS, heat (N-bromosuccinimide)

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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)
(3)
OH
OH
trans-1,2-cyclohexanediol
(racemic)
Submit Answer
(c) ethylene oxide
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
(a) CH₂O¯Na+, CH3OH (d) H₂SO4, H₂O
(b) OsO4, H₂O2
Retry Entire Group
OH
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromate
(PCC)
+
8 more group attempts remaining
(2)
(g) H₂SO4 (anhydrous) (j) Na, NH3 (1)
(h) NaOH
(k) NBS, heat
(i) PBr3
(N-bromosuccinimide)
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Transcribed Image Text:Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. (1) (3) OH OH trans-1,2-cyclohexanediol (racemic) Submit Answer (c) ethylene oxide 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 (a) CH₂O¯Na+, CH3OH (d) H₂SO4, H₂O (b) OsO4, H₂O2 Retry Entire Group OH (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) + 8 more group attempts remaining (2) (g) H₂SO4 (anhydrous) (j) Na, NH3 (1) (h) NaOH (k) NBS, heat (i) PBr3 (N-bromosuccinimide) Previous Next
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