Chapter 31: Q34P. (page 1259)
Axial alcohols are oxidized faster than equatorial alcohols by PCC and other oxidants. Which OH group in each compound is oxidized faster?
a.
b.
Short Answer
Answer
a.
b.
Chapter 31: Q34P. (page 1259)
Axial alcohols are oxidized faster than equatorial alcohols by PCC and other oxidants. Which OH group in each compound is oxidized faster?
a.
b.
Answer
a.
b.
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A difficult problem in the synthesis of PGFis the introduction of the OH group at C15 in the desired configuration.
A well known synthesis of PGFinvolves reaction of A with (a metal hydride reagent similar in reactivity to, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.
Suggest a reagent to convert A to the single stereoisomer X.
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One component of lanolin, the wax that coats sheep’s wool, is derived from cholesterol and stearic acid. Draw its structure, including the correct stereochemistry of all stereogenic centers.
Draw three-dimensional structures for each alcohol. Label the OH groups as occupying axial or equatorial positions.
a.
b.
c.
d.
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