Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. (1) (2) OH (3) OH trans-1,2-cyclohexanediol (racemic) 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: OH (a) CH3O Na+, CH3 OF (d) H₂SO (b) OsO4, H₂O2 (c) ethylene oxide H₂O (e) m-chloroperoxybenzoic acid (g) O4 (anhy (h) NaOH O (mCPBA) (f) pyridinium chlorochromate) PBr3 (PCC) us) Na, NH3 (1) (k) NBS, heat (N-bromosuccinimide)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 28VC
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Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol.
(1)
(2)
OH
aa
OH
(3)
trans-1,2-cyclohexanediol
(racemic)
OH
"ОН
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
1
OH
(a) CH3ONa+, CH, OH (d) H₂SO4, H₂O
(b) OsO4, H₂O2
||Ⓡ
(9) H₂SO4 (anhydrou$)) Na, NH3 (1)
(k) NBS, heat
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromatę) PBr3
(PCC)
(h) NaOH
(N-bromosuccinimide)
Transcribed Image Text:Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. (1) (2) OH aa OH (3) trans-1,2-cyclohexanediol (racemic) OH "ОН Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: (c) ethylene oxide 1 OH (a) CH3ONa+, CH, OH (d) H₂SO4, H₂O (b) OsO4, H₂O2 ||Ⓡ (9) H₂SO4 (anhydrou$)) Na, NH3 (1) (k) NBS, heat (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromatę) PBr3 (PCC) (h) NaOH (N-bromosuccinimide)
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