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

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
Chapter9: Nucleophilic Substitution And Β-elimination
Section: Chapter Questions
Problem 9.46P: When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the...
icon
Related questions
Question
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
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 3 images

Blurred answer
Knowledge Booster
Organomagnesium Compounds
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning