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Is Cyclic Ether oxidised by periodic acid
What's the reaction type of the Hydrogen shift?How do you make sense of acid base reactions in organic chemistry?Rearrangement of an oxyallyl cationDeciding more electrophilic centre between ester and thioester for SN type reactionWhat will methyl (2-oxocyclohexyl)acetate produce when reacted with sodium borohydride?Acid Catalysed Ring Expansion – Mechanism?Formation of (Gamma) Methylparaconic acidReaction of urea and thiourea with nitrous acidWhy does Oxygen act as Nucleophile over here?What is the total number of isomers, considering both structural and stereoisomers of cyclic ethers with the molecular formula C4H8O?
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$begingroup$
Is three member ring of cyclic Ether oxidised by periodic acid?
As this also has oxygen attached to adjacent carbon so i think that Cyclic Ether of three members should be oxidised by periodic acid.
I know the mechanism of oxidation of 1,2 diols by periodic acid but ain't able to relate to this question.
Please help me out here.
organic-chemistry
asked 9 hours ago
Smit PatelSmit Patel
211 bronze badge
New contributor
Smit Patel is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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$endgroup$
add a comment |
$begingroup$
Is three member ring of cyclic Ether oxidised by periodic acid?
As this also has oxygen attached to adjacent carbon so i think that Cyclic Ether of three members should be oxidised by periodic acid.
I know the mechanism of oxidation of 1,2 diols by periodic acid but ain't able to relate to this question.
Please help me out here.
organic-chemistry
asked 9 hours ago
Smit PatelSmit Patel
211 bronze badge
New contributor
Smit Patel is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
2
$begingroup$
Well if you manage to hydrolyse the oxirane first I suppose it will oxidize it.
$endgroup$
– William R. Ebenezer
8 hours ago
add a comment |
$begingroup$
Is three member ring of cyclic Ether oxidised by periodic acid?
As this also has oxygen attached to adjacent carbon so i think that Cyclic Ether of three members should be oxidised by periodic acid.
I know the mechanism of oxidation of 1,2 diols by periodic acid but ain't able to relate to this question.
Please help me out here.
organic-chemistry
asked 9 hours ago
Smit PatelSmit Patel
211 bronze badge
New contributor
Smit Patel is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
Is three member ring of cyclic Ether oxidised by periodic acid?
As this also has oxygen attached to adjacent carbon so i think that Cyclic Ether of three members should be oxidised by periodic acid.
I know the mechanism of oxidation of 1,2 diols by periodic acid but ain't able to relate to this question.
Please help me out here.
organic-chemistry
organic-chemistry
asked 9 hours ago
Smit PatelSmit Patel
211 bronze badge
New contributor
Smit Patel is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 9 hours ago
Smit PatelSmit Patel
211 bronze badge
New contributor
Smit Patel is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 9 hours ago
Smit PatelSmit Patel
211 bronze badge
New contributor
Smit Patel is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 9 hours ago
Smit PatelSmit Patel
211 bronze badge
asked 9 hours ago
Smit PatelSmit Patel
211 bronze badge
211 bronze badge
New contributor
Smit Patel is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
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2
$begingroup$
Well if you manage to hydrolyse the oxirane first I suppose it will oxidize it.
$endgroup$
– William R. Ebenezer
8 hours ago
add a comment |
2
$begingroup$
Well if you manage to hydrolyse the oxirane first I suppose it will oxidize it.
$endgroup$
– William R. Ebenezer
8 hours ago
2
2
$begingroup$
Well if you manage to hydrolyse the oxirane first I suppose it will oxidize it.
$endgroup$
– William R. Ebenezer
8 hours ago
$begingroup$
Well if you manage to hydrolyse the oxirane first I suppose it will oxidize it.
$endgroup$
– William R. Ebenezer
8 hours ago
add a comment |
2 Answers
2
active
oldest
votes
$begingroup$
Cyclic ethers usually do not get oxidized by periodic acid. However, epoxides would do only if they were acidified first or use acidified periodic acid in the reaction (Ref.1). In general, acidified periodic acid has been used as a qualitative test for the presence of epoxide moiety in organic compounds (Ref.1). The procedure is a modification of the qualitative test for glycols (Ref.2). Hence, epoxide must be converted to 1,2-diols first by acid and oxidation by periodic acid must be followed. The test is described as follows:
Exactly 2 drops of concentrated nitric acid is added to 2 ml. of a 0.5% solution of periodic acid, and 1 or 2 drops of the unknown is added. Water-insoluble unknowns should first be dissolved in 2 ml. of dioxane or acetic acid. The mixture is shaken and 1 or 2 drops of 5% silver nitrate is added at room temperature. A positive test is the appearance of a white precipitate of silver iodate which usually forms immediately, but may require up to 5 minutes for complete precipitation. In all cases a blank should be run for comparison. The test is negative for simple aldehydes, ketones, and alcohols.
References:
- R. Fuchs, R. C. Waters, C. A. Vanderwerf, “General Qualitative Test for Epoxides,” Anal. Chem. 1952, 24(9), 1514 (https://doi.org/10.1021/ac60069a047).
- R. L. Shriner, R. C. Fuson, Identification of Organic Compounds; 3rd ed., John Wiley & Sons: New York, NY, 1948, pp. 115-116.
answered 4 hours ago
Mathew MahindaratneMathew Mahindaratne
9,3951 gold badge11 silver badges33 bronze badges
$endgroup$
add a comment |
$begingroup$
This quote is from Comprehensive Organic Name Reactions and Reagents by Zerong Wang.
The oxidation of adjacent diols with periodic acid or its salt in aqueous solution is generally known as the Malaprade reaction. Several solvents have been used to increase the solubility of organic substrates and the reaction proceeds faster under acidic conditions. This reaction has been further extended to the cleavage of α‐hydroxy carbonyl compounds, 1,2‐dicarbonyl compounds, α‐amino alcohols, α‐amino acids, and polyhydroxy alcohols. .
The mechanism of Malaprade reaction reaction is as follows:
As per the requirements of mechanism , the three membred ether should be converted to a adjacent diols (viscinal) diol for it to be oxidised by periodic acid.
answered 6 hours ago
Chakravarthy KalyanChakravarthy Kalyan
2,1895 silver badges22 bronze badges
$endgroup$
add a comment |
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2 Answers
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2 Answers
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$begingroup$
Cyclic ethers usually do not get oxidized by periodic acid. However, epoxides would do only if they were acidified first or use acidified periodic acid in the reaction (Ref.1). In general, acidified periodic acid has been used as a qualitative test for the presence of epoxide moiety in organic compounds (Ref.1). The procedure is a modification of the qualitative test for glycols (Ref.2). Hence, epoxide must be converted to 1,2-diols first by acid and oxidation by periodic acid must be followed. The test is described as follows:
Exactly 2 drops of concentrated nitric acid is added to 2 ml. of a 0.5% solution of periodic acid, and 1 or 2 drops of the unknown is added. Water-insoluble unknowns should first be dissolved in 2 ml. of dioxane or acetic acid. The mixture is shaken and 1 or 2 drops of 5% silver nitrate is added at room temperature. A positive test is the appearance of a white precipitate of silver iodate which usually forms immediately, but may require up to 5 minutes for complete precipitation. In all cases a blank should be run for comparison. The test is negative for simple aldehydes, ketones, and alcohols.
References:
- R. Fuchs, R. C. Waters, C. A. Vanderwerf, “General Qualitative Test for Epoxides,” Anal. Chem. 1952, 24(9), 1514 (https://doi.org/10.1021/ac60069a047).
- R. L. Shriner, R. C. Fuson, Identification of Organic Compounds; 3rd ed., John Wiley & Sons: New York, NY, 1948, pp. 115-116.
answered 4 hours ago
Mathew MahindaratneMathew Mahindaratne
9,3951 gold badge11 silver badges33 bronze badges
$endgroup$
add a comment |
$begingroup$
Cyclic ethers usually do not get oxidized by periodic acid. However, epoxides would do only if they were acidified first or use acidified periodic acid in the reaction (Ref.1). In general, acidified periodic acid has been used as a qualitative test for the presence of epoxide moiety in organic compounds (Ref.1). The procedure is a modification of the qualitative test for glycols (Ref.2). Hence, epoxide must be converted to 1,2-diols first by acid and oxidation by periodic acid must be followed. The test is described as follows:
Exactly 2 drops of concentrated nitric acid is added to 2 ml. of a 0.5% solution of periodic acid, and 1 or 2 drops of the unknown is added. Water-insoluble unknowns should first be dissolved in 2 ml. of dioxane or acetic acid. The mixture is shaken and 1 or 2 drops of 5% silver nitrate is added at room temperature. A positive test is the appearance of a white precipitate of silver iodate which usually forms immediately, but may require up to 5 minutes for complete precipitation. In all cases a blank should be run for comparison. The test is negative for simple aldehydes, ketones, and alcohols.
References:
- R. Fuchs, R. C. Waters, C. A. Vanderwerf, “General Qualitative Test for Epoxides,” Anal. Chem. 1952, 24(9), 1514 (https://doi.org/10.1021/ac60069a047).
- R. L. Shriner, R. C. Fuson, Identification of Organic Compounds; 3rd ed., John Wiley & Sons: New York, NY, 1948, pp. 115-116.
answered 4 hours ago
Mathew MahindaratneMathew Mahindaratne
9,3951 gold badge11 silver badges33 bronze badges
$endgroup$
add a comment |
$begingroup$
Cyclic ethers usually do not get oxidized by periodic acid. However, epoxides would do only if they were acidified first or use acidified periodic acid in the reaction (Ref.1). In general, acidified periodic acid has been used as a qualitative test for the presence of epoxide moiety in organic compounds (Ref.1). The procedure is a modification of the qualitative test for glycols (Ref.2). Hence, epoxide must be converted to 1,2-diols first by acid and oxidation by periodic acid must be followed. The test is described as follows:
Exactly 2 drops of concentrated nitric acid is added to 2 ml. of a 0.5% solution of periodic acid, and 1 or 2 drops of the unknown is added. Water-insoluble unknowns should first be dissolved in 2 ml. of dioxane or acetic acid. The mixture is shaken and 1 or 2 drops of 5% silver nitrate is added at room temperature. A positive test is the appearance of a white precipitate of silver iodate which usually forms immediately, but may require up to 5 minutes for complete precipitation. In all cases a blank should be run for comparison. The test is negative for simple aldehydes, ketones, and alcohols.
References:
- R. Fuchs, R. C. Waters, C. A. Vanderwerf, “General Qualitative Test for Epoxides,” Anal. Chem. 1952, 24(9), 1514 (https://doi.org/10.1021/ac60069a047).
- R. L. Shriner, R. C. Fuson, Identification of Organic Compounds; 3rd ed., John Wiley & Sons: New York, NY, 1948, pp. 115-116.
answered 4 hours ago
Mathew MahindaratneMathew Mahindaratne
9,3951 gold badge11 silver badges33 bronze badges
$endgroup$
Cyclic ethers usually do not get oxidized by periodic acid. However, epoxides would do only if they were acidified first or use acidified periodic acid in the reaction (Ref.1). In general, acidified periodic acid has been used as a qualitative test for the presence of epoxide moiety in organic compounds (Ref.1). The procedure is a modification of the qualitative test for glycols (Ref.2). Hence, epoxide must be converted to 1,2-diols first by acid and oxidation by periodic acid must be followed. The test is described as follows:
Exactly 2 drops of concentrated nitric acid is added to 2 ml. of a 0.5% solution of periodic acid, and 1 or 2 drops of the unknown is added. Water-insoluble unknowns should first be dissolved in 2 ml. of dioxane or acetic acid. The mixture is shaken and 1 or 2 drops of 5% silver nitrate is added at room temperature. A positive test is the appearance of a white precipitate of silver iodate which usually forms immediately, but may require up to 5 minutes for complete precipitation. In all cases a blank should be run for comparison. The test is negative for simple aldehydes, ketones, and alcohols.
References:
- R. Fuchs, R. C. Waters, C. A. Vanderwerf, “General Qualitative Test for Epoxides,” Anal. Chem. 1952, 24(9), 1514 (https://doi.org/10.1021/ac60069a047).
- R. L. Shriner, R. C. Fuson, Identification of Organic Compounds; 3rd ed., John Wiley & Sons: New York, NY, 1948, pp. 115-116.
answered 4 hours ago
Mathew MahindaratneMathew Mahindaratne
9,3951 gold badge11 silver badges33 bronze badges
answered 4 hours ago
Mathew MahindaratneMathew Mahindaratne
9,3951 gold badge11 silver badges33 bronze badges
answered 4 hours ago
Mathew MahindaratneMathew Mahindaratne
9,3951 gold badge11 silver badges33 bronze badges
answered 4 hours ago
Mathew MahindaratneMathew Mahindaratne
9,3951 gold badge11 silver badges33 bronze badges
9,3951 gold badge11 silver badges33 bronze badges
add a comment |
add a comment |
$begingroup$
This quote is from Comprehensive Organic Name Reactions and Reagents by Zerong Wang.
The oxidation of adjacent diols with periodic acid or its salt in aqueous solution is generally known as the Malaprade reaction. Several solvents have been used to increase the solubility of organic substrates and the reaction proceeds faster under acidic conditions. This reaction has been further extended to the cleavage of α‐hydroxy carbonyl compounds, 1,2‐dicarbonyl compounds, α‐amino alcohols, α‐amino acids, and polyhydroxy alcohols. .
The mechanism of Malaprade reaction reaction is as follows:
As per the requirements of mechanism , the three membred ether should be converted to a adjacent diols (viscinal) diol for it to be oxidised by periodic acid.
answered 6 hours ago
Chakravarthy KalyanChakravarthy Kalyan
2,1895 silver badges22 bronze badges
$endgroup$
add a comment |
$begingroup$
This quote is from Comprehensive Organic Name Reactions and Reagents by Zerong Wang.
The oxidation of adjacent diols with periodic acid or its salt in aqueous solution is generally known as the Malaprade reaction. Several solvents have been used to increase the solubility of organic substrates and the reaction proceeds faster under acidic conditions. This reaction has been further extended to the cleavage of α‐hydroxy carbonyl compounds, 1,2‐dicarbonyl compounds, α‐amino alcohols, α‐amino acids, and polyhydroxy alcohols. .
The mechanism of Malaprade reaction reaction is as follows:
As per the requirements of mechanism , the three membred ether should be converted to a adjacent diols (viscinal) diol for it to be oxidised by periodic acid.
answered 6 hours ago
Chakravarthy KalyanChakravarthy Kalyan
2,1895 silver badges22 bronze badges
$endgroup$
add a comment |
$begingroup$
This quote is from Comprehensive Organic Name Reactions and Reagents by Zerong Wang.
The oxidation of adjacent diols with periodic acid or its salt in aqueous solution is generally known as the Malaprade reaction. Several solvents have been used to increase the solubility of organic substrates and the reaction proceeds faster under acidic conditions. This reaction has been further extended to the cleavage of α‐hydroxy carbonyl compounds, 1,2‐dicarbonyl compounds, α‐amino alcohols, α‐amino acids, and polyhydroxy alcohols. .
The mechanism of Malaprade reaction reaction is as follows:
As per the requirements of mechanism , the three membred ether should be converted to a adjacent diols (viscinal) diol for it to be oxidised by periodic acid.
answered 6 hours ago
Chakravarthy KalyanChakravarthy Kalyan
2,1895 silver badges22 bronze badges
$endgroup$
This quote is from Comprehensive Organic Name Reactions and Reagents by Zerong Wang.
The oxidation of adjacent diols with periodic acid or its salt in aqueous solution is generally known as the Malaprade reaction. Several solvents have been used to increase the solubility of organic substrates and the reaction proceeds faster under acidic conditions. This reaction has been further extended to the cleavage of α‐hydroxy carbonyl compounds, 1,2‐dicarbonyl compounds, α‐amino alcohols, α‐amino acids, and polyhydroxy alcohols. .
The mechanism of Malaprade reaction reaction is as follows:
As per the requirements of mechanism , the three membred ether should be converted to a adjacent diols (viscinal) diol for it to be oxidised by periodic acid.
answered 6 hours ago
Chakravarthy KalyanChakravarthy Kalyan
2,1895 silver badges22 bronze badges
answered 6 hours ago
Chakravarthy KalyanChakravarthy Kalyan
2,1895 silver badges22 bronze badges
answered 6 hours ago
Chakravarthy KalyanChakravarthy Kalyan
2,1895 silver badges22 bronze badges
answered 6 hours ago
Chakravarthy KalyanChakravarthy Kalyan
2,1895 silver badges22 bronze badges
2,1895 silver badges22 bronze badges
add a comment |
add a comment |
Smit Patel is a new contributor. Be nice, and check out our Code of Conduct.
Smit Patel is a new contributor. Be nice, and check out our Code of Conduct.
Smit Patel is a new contributor. Be nice, and check out our Code of Conduct.
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$begingroup$
Well if you manage to hydrolyse the oxirane first I suppose it will oxidize it.
$endgroup$
– William R. Ebenezer
8 hours ago