
Concept explainers
a)
Interpretation:
How to prepare the
Concept introduction:
A cis diol can be prepared by treating an
A trans diol can be prepared by acid catalyzed ring opening of
To state:
How to prepare the diol shown.
b)
Interpretation:
How to prepare the diol shown is to be stated.
Concept introduction:
A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO3 yields the cis diol.
A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.
To state:
How to prepare the diol shown.

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Chapter 18 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
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