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Chapter 8-14 - Syn Hydroxylation of Alkenes
Organic Chemistry 307: Chapter 8 - Reactions of Alkenes; Section 14 - Syn Hydroxylation of Alkenes
Organic Chemistry
Undergraduate 3

Additional Organic Chemistry Flashcards




A __________ (or __________) is a reaction in which a hydroxyl group is added to each end of a double bonded alkene.
1) Hydroxylation
2) Dihydroxylation
__________ of an alkene followed by acidic hydrolysis gives __________ hydroxylation of the double bond.
1) Epoxidation
2) Anti
__________ __________ (OsO4, sometimes called __________ __________) reacts with alkenes in a concerted step form a cyclic osmate ester.
Oxidizing agents such as __________ __________ (H2O2) or tertiary __________ oxides (R3N+-O-) are used to hydrolyze the osmate ester and reoxidize osmium to __________ __________.
The regenerated __________ __________ catalyst continues to hydroxylate more molecules of the alkene.
1) Osmium tetroxide
2) Osmic acid
3) Hydrogen peroxide
4) Amine
5) Osmium tetroxide
6) Osmium tetroxide
In the hydroxylation of osmium tetroxide, since the two carbon-oxygen bonds are formed simultaneously with the cyclic __________ __________, the __________ atoms add to the same face if the double bond; that is, with __________ stereochemistry.
1) Osmate ester
2) Oxygen
3) Syn
A cold, dilute solution of __________ __________ also hydroxylates alkenes with __________ stereochemistry, with slightly reduced yields.
Like osmium tetroxide, __________ __________ adds to the alkene double bond to form a cyclic ester: a __________ ester in this case.
The __________ solution hydrolyzes the manganate ester, liberating the __________ and produce a brown precipitate of manganese dioxide.
1) Potassium permanganate
2) Syn
3) Potassium permanganate
4) Manganate
5) Basic
6) Glycol
To hydroxylate an alkene with __________ stereochemistry, which is the better reagent: __________ __________ or __________ __________? It depends on the circumstances:
If the starting material is only 2 mg of a compound 15 steps along in a difficult synthesis, we use __________ __________.
If the hydroxylation is the first step in a synthesis and involves 5 kg of the starting material, we use __________ __________.
1) Syn
2) Osmium tetroxide
3) Potassium permanganate
4) Osmium tetroxide
5) Potassium permanganate
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