Which set of reagents would convert an alkene to a vicinal diol via syn addition?
A
in water
B
with catalyst
C
followed by and water
D
followed by and acetic acid
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1
Understand that a vicinal diol is a molecule where two hydroxyl (–OH) groups are attached to adjacent carbon atoms.
Recall that syn addition means both –OH groups add to the same face (side) of the alkene, resulting in a specific stereochemical outcome.
Review the common reagents for dihydroxylation of alkenes: \( \mathrm{OsO_4} \) (osmium tetroxide) is known to add two hydroxyl groups across the double bond in a syn fashion.
Note that \( \mathrm{OsO_4} \) is typically followed by a reducing agent such as \( \mathrm{NaHSO_3} \) in water to regenerate the catalyst and complete the reaction, giving the vicinal diol.
Contrast this with other reagents: \( \mathrm{Br_2} \) in water gives anti addition, \( \mathrm{H_2} \) with Pt catalyst gives hydrogenation (alkane), and \( \mathrm{O_3} \) followed by Zn/acetic acid leads to ozonolysis (cleavage), not diol formation.