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Questions and Answers
What is the major product of the reaction of indole with benzoyl nitrate in acetonitrile?
What is the major product of the reaction of indole with benzoyl nitrate in acetonitrile?
What is the product of the nitrosation of 2-methylindole with sodium nitrite in the presence of acetic acid?
What is the product of the nitrosation of 2-methylindole with sodium nitrite in the presence of acetic acid?
What is the product of the chlorination of indole with an excess of sulfuryl chloride?
What is the product of the chlorination of indole with an excess of sulfuryl chloride?
What is the product of the bromination of indole when the position-3 is already substituted?
What is the product of the bromination of indole when the position-3 is already substituted?
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What is the product of the sulfonation of indole with pyridine-sulfur trioxide complex?
What is the product of the sulfonation of indole with pyridine-sulfur trioxide complex?
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What is the product of the Vilsmeier-Haack formylation of indole?
What is the product of the Vilsmeier-Haack formylation of indole?
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What is the effect of the presence of sodium ethoxide on the nitration of indole?
What is the effect of the presence of sodium ethoxide on the nitration of indole?
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What is the product of the reaction of 3-methylindole with sodium nitrite in the presence of acetic acid?
What is the product of the reaction of 3-methylindole with sodium nitrite in the presence of acetic acid?
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What is the intermediate in the chlorination of indole with an excess of sulfuryl chloride?
What is the intermediate in the chlorination of indole with an excess of sulfuryl chloride?
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What is the effect of the acid sensitivity of indole on its reactions with electrophiles?
What is the effect of the acid sensitivity of indole on its reactions with electrophiles?
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Study Notes
Nitration of Indole
- Nitration of indole with benzoyl nitrate in acetonitrile or with ethyl nitrate in the presence of sodium ethoxide at low temperature yields 3-nitroindole.
- Reaction conditions affect the products of nitration of indoles with different nitrating agents.
Nitrosation of Indole
- Nitrosation of 2-methylindole with sodium nitrite in the presence of acetic acid occurs at position-3, forming 3-oximino-2-methylindole (or 3-nitroso-2-methylindole).
- Nitrosation of 3-methylindole yields N-nitroso-3-methylindole.
Halogenation of Indole
Chlorination
- Chlorination of indole with sulfuryl chloride produces 3-chloroindole.
- Excess sulfuryl chloride leads to the formation of 2,3-dichloroindole via 3,3-dichloro-3H-indole.
Bromination
- Bromination of indole occurs at position-3, forming 3-bromoindole.
- If position-3 is already substituted, bromination takes place at position-2.
Sulfonation of Indole
- Indole is sulfonated with pyridine-sulfur trioxide complex, yielding indole-3-sulfonic acid.
- If position-3 is already occupied, sulfonation occurs at position-2 via an initial reversible sulfonation at position-3.
Vilsmeier-Haack Formylation
- Indole undergoes Vilsmeier-Haack formylation with N,N-dimethylformamide (DMF) in the presence of phosphorus oxychloride, forming 3-formylindole.
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Description
This quiz covers the reactions of indoles with electrophiles, specifically nitration and nitrosation reactions, including the effects of different reaction conditions and agents.
