How there are 3 possible tautomers of 2,2,4-trimethylheptane-3,5-dione?Major form of methyl 3-hydroxy pent-2-enoate?Why tautomers are considered to be the same chemical compound?Can a tertiary enamine tautomerize to an imine?Is carbonyl-enol tautomerization only intermolecular or can it be intramolecular?On the oxyacids of +III pnictogens and +IV chalcogensWhat is the most stable structure amongst the keto-enol tautomers of pentane-2,4-dione?Compound having the highest enol content will be?
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How there are 3 possible tautomers of 2,2,4-trimethylheptane-3,5-dione?
Major form of methyl 3-hydroxy pent-2-enoate?Why tautomers are considered to be the same chemical compound?Can a tertiary enamine tautomerize to an imine?Is carbonyl-enol tautomerization only intermolecular or can it be intramolecular?On the oxyacids of +III pnictogens and +IV chalcogensWhat is the most stable structure amongst the keto-enol tautomers of pentane-2,4-dione?Compound having the highest enol content will be?
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$begingroup$
The answer for the above question is 3. But I am able to draw 4 structures:
Where am I getting wrong?
tautomer
edited 6 hours ago
Loong♦
37.1k9 gold badges92 silver badges196 bronze badges
asked 8 hours ago
Garima SinghGarima Singh
833 bronze badges
$endgroup$
add a comment |
$begingroup$
The answer for the above question is 3. But I am able to draw 4 structures:
Where am I getting wrong?
tautomer
edited 6 hours ago
Loong♦
37.1k9 gold badges92 silver badges196 bronze badges
asked 8 hours ago
Garima SinghGarima Singh
833 bronze badges
$endgroup$
$begingroup$
The last structure does not really exist in slightly acidified solution of the given compound.
$endgroup$
– J_B892
7 hours ago
$begingroup$
Coming to this question won't even cis and trans also contribute to Number of tautomers?
$endgroup$
– J_B892
7 hours ago
$begingroup$
yes I was confused whether last structure is correct or not. but don't know the reason to eliminate it. why it doesn't exist in acidified solution? also if we make the cis and trans structure as well then we will have more than 4 structures which are not in the option. that means the question is just asking the standard structures.
$endgroup$
– Garima Singh
7 hours ago
$begingroup$
Once you do a single tautomerism there's a hydrogen bonding (6 membered ring) formed between -OH and the oxygen. This gives stability to the compound and prefers not to further tautomerise
$endgroup$
– J_B892
7 hours ago
add a comment |
$begingroup$
The answer for the above question is 3. But I am able to draw 4 structures:
Where am I getting wrong?
tautomer
edited 6 hours ago
Loong♦
37.1k9 gold badges92 silver badges196 bronze badges
asked 8 hours ago
Garima SinghGarima Singh
833 bronze badges
$endgroup$
The answer for the above question is 3. But I am able to draw 4 structures:
Where am I getting wrong?
tautomer
tautomer
edited 6 hours ago
Loong♦
37.1k9 gold badges92 silver badges196 bronze badges
asked 8 hours ago
Garima SinghGarima Singh
833 bronze badges
edited 6 hours ago
Loong♦
37.1k9 gold badges92 silver badges196 bronze badges
asked 8 hours ago
Garima SinghGarima Singh
833 bronze badges
edited 6 hours ago
Loong♦
37.1k9 gold badges92 silver badges196 bronze badges
edited 6 hours ago
Loong♦
37.1k9 gold badges92 silver badges196 bronze badges
edited 6 hours ago
Loong♦
37.1k9 gold badges92 silver badges196 bronze badges
37.1k9 gold badges92 silver badges196 bronze badges
asked 8 hours ago
Garima SinghGarima Singh
833 bronze badges
asked 8 hours ago
Garima SinghGarima Singh
833 bronze badges
asked 8 hours ago
Garima SinghGarima Singh
833 bronze badges
833 bronze badges
$begingroup$
The last structure does not really exist in slightly acidified solution of the given compound.
$endgroup$
– J_B892
7 hours ago
$begingroup$
Coming to this question won't even cis and trans also contribute to Number of tautomers?
$endgroup$
– J_B892
7 hours ago
$begingroup$
yes I was confused whether last structure is correct or not. but don't know the reason to eliminate it. why it doesn't exist in acidified solution? also if we make the cis and trans structure as well then we will have more than 4 structures which are not in the option. that means the question is just asking the standard structures.
$endgroup$
– Garima Singh
7 hours ago
$begingroup$
Once you do a single tautomerism there's a hydrogen bonding (6 membered ring) formed between -OH and the oxygen. This gives stability to the compound and prefers not to further tautomerise
$endgroup$
– J_B892
7 hours ago
add a comment |
$begingroup$
The last structure does not really exist in slightly acidified solution of the given compound.
$endgroup$
– J_B892
7 hours ago
$begingroup$
Coming to this question won't even cis and trans also contribute to Number of tautomers?
$endgroup$
– J_B892
7 hours ago
$begingroup$
yes I was confused whether last structure is correct or not. but don't know the reason to eliminate it. why it doesn't exist in acidified solution? also if we make the cis and trans structure as well then we will have more than 4 structures which are not in the option. that means the question is just asking the standard structures.
$endgroup$
– Garima Singh
7 hours ago
$begingroup$
Once you do a single tautomerism there's a hydrogen bonding (6 membered ring) formed between -OH and the oxygen. This gives stability to the compound and prefers not to further tautomerise
$endgroup$
– J_B892
7 hours ago
$begingroup$
The last structure does not really exist in slightly acidified solution of the given compound.
$endgroup$
– J_B892
7 hours ago
$begingroup$
The last structure does not really exist in slightly acidified solution of the given compound.
$endgroup$
– J_B892
7 hours ago
$begingroup$
Coming to this question won't even cis and trans also contribute to Number of tautomers?
$endgroup$
– J_B892
7 hours ago
$begingroup$
Coming to this question won't even cis and trans also contribute to Number of tautomers?
$endgroup$
– J_B892
7 hours ago
$begingroup$
yes I was confused whether last structure is correct or not. but don't know the reason to eliminate it. why it doesn't exist in acidified solution? also if we make the cis and trans structure as well then we will have more than 4 structures which are not in the option. that means the question is just asking the standard structures.
$endgroup$
– Garima Singh
7 hours ago
$begingroup$
yes I was confused whether last structure is correct or not. but don't know the reason to eliminate it. why it doesn't exist in acidified solution? also if we make the cis and trans structure as well then we will have more than 4 structures which are not in the option. that means the question is just asking the standard structures.
$endgroup$
– Garima Singh
7 hours ago
$begingroup$
Once you do a single tautomerism there's a hydrogen bonding (6 membered ring) formed between -OH and the oxygen. This gives stability to the compound and prefers not to further tautomerise
$endgroup$
– J_B892
7 hours ago
$begingroup$
Once you do a single tautomerism there's a hydrogen bonding (6 membered ring) formed between -OH and the oxygen. This gives stability to the compound and prefers not to further tautomerise
$endgroup$
– J_B892
7 hours ago
add a comment |
2 Answers
2
active
oldest
votes
$begingroup$
In your attempt the 4th compound is not reported to have significant percentage in solution (acidic or basic). This is because once the tautomerisation occurs for example let's say the 1st compound, there is a tautomer having a six-membered conjugated ring involving H-bonding. This thereby increases the stability of the compound and consequently increasing the activation energy for the tautomerisation you proposed in compound 4. This is why compound 4 is not formed.
Also keep in mind that stereo-chemistry is also important while finding number of possible compounds.
Hope this helps!
answered 6 hours ago
J_B892J_B892
4634 silver badges17 bronze badges
$endgroup$
add a comment |
$begingroup$
When a tautomer is formed from a diketone, a six-membered pesudo-ring structure is formed that stabilizes the structure through H-bonding. This structure is responsible for not letting any tautomerization of the second carbonyl.
Note: the structure I've shown on the top is made from MS Paint so its quite messy but you'll get the point.
answered 5 hours ago
Kent de los ReyesKent de los Reyes
24110 bronze badges
$endgroup$
add a comment |
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2 Answers
2
active
oldest
votes
2 Answers
2
active
oldest
votes
active
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votes
active
oldest
votes
$begingroup$
In your attempt the 4th compound is not reported to have significant percentage in solution (acidic or basic). This is because once the tautomerisation occurs for example let's say the 1st compound, there is a tautomer having a six-membered conjugated ring involving H-bonding. This thereby increases the stability of the compound and consequently increasing the activation energy for the tautomerisation you proposed in compound 4. This is why compound 4 is not formed.
Also keep in mind that stereo-chemistry is also important while finding number of possible compounds.
Hope this helps!
answered 6 hours ago
J_B892J_B892
4634 silver badges17 bronze badges
$endgroup$
add a comment |
$begingroup$
In your attempt the 4th compound is not reported to have significant percentage in solution (acidic or basic). This is because once the tautomerisation occurs for example let's say the 1st compound, there is a tautomer having a six-membered conjugated ring involving H-bonding. This thereby increases the stability of the compound and consequently increasing the activation energy for the tautomerisation you proposed in compound 4. This is why compound 4 is not formed.
Also keep in mind that stereo-chemistry is also important while finding number of possible compounds.
Hope this helps!
answered 6 hours ago
J_B892J_B892
4634 silver badges17 bronze badges
$endgroup$
add a comment |
$begingroup$
In your attempt the 4th compound is not reported to have significant percentage in solution (acidic or basic). This is because once the tautomerisation occurs for example let's say the 1st compound, there is a tautomer having a six-membered conjugated ring involving H-bonding. This thereby increases the stability of the compound and consequently increasing the activation energy for the tautomerisation you proposed in compound 4. This is why compound 4 is not formed.
Also keep in mind that stereo-chemistry is also important while finding number of possible compounds.
Hope this helps!
answered 6 hours ago
J_B892J_B892
4634 silver badges17 bronze badges
$endgroup$
In your attempt the 4th compound is not reported to have significant percentage in solution (acidic or basic). This is because once the tautomerisation occurs for example let's say the 1st compound, there is a tautomer having a six-membered conjugated ring involving H-bonding. This thereby increases the stability of the compound and consequently increasing the activation energy for the tautomerisation you proposed in compound 4. This is why compound 4 is not formed.
Also keep in mind that stereo-chemistry is also important while finding number of possible compounds.
Hope this helps!
answered 6 hours ago
J_B892J_B892
4634 silver badges17 bronze badges
answered 6 hours ago
J_B892J_B892
4634 silver badges17 bronze badges
answered 6 hours ago
J_B892J_B892
4634 silver badges17 bronze badges
answered 6 hours ago
J_B892J_B892
4634 silver badges17 bronze badges
4634 silver badges17 bronze badges
add a comment |
add a comment |
$begingroup$
When a tautomer is formed from a diketone, a six-membered pesudo-ring structure is formed that stabilizes the structure through H-bonding. This structure is responsible for not letting any tautomerization of the second carbonyl.
Note: the structure I've shown on the top is made from MS Paint so its quite messy but you'll get the point.
answered 5 hours ago
Kent de los ReyesKent de los Reyes
24110 bronze badges
$endgroup$
add a comment |
$begingroup$
When a tautomer is formed from a diketone, a six-membered pesudo-ring structure is formed that stabilizes the structure through H-bonding. This structure is responsible for not letting any tautomerization of the second carbonyl.
Note: the structure I've shown on the top is made from MS Paint so its quite messy but you'll get the point.
answered 5 hours ago
Kent de los ReyesKent de los Reyes
24110 bronze badges
$endgroup$
add a comment |
$begingroup$
When a tautomer is formed from a diketone, a six-membered pesudo-ring structure is formed that stabilizes the structure through H-bonding. This structure is responsible for not letting any tautomerization of the second carbonyl.
Note: the structure I've shown on the top is made from MS Paint so its quite messy but you'll get the point.
answered 5 hours ago
Kent de los ReyesKent de los Reyes
24110 bronze badges
$endgroup$
When a tautomer is formed from a diketone, a six-membered pesudo-ring structure is formed that stabilizes the structure through H-bonding. This structure is responsible for not letting any tautomerization of the second carbonyl.
Note: the structure I've shown on the top is made from MS Paint so its quite messy but you'll get the point.
answered 5 hours ago
Kent de los ReyesKent de los Reyes
24110 bronze badges
answered 5 hours ago
Kent de los ReyesKent de los Reyes
24110 bronze badges
answered 5 hours ago
Kent de los ReyesKent de los Reyes
24110 bronze badges
answered 5 hours ago
Kent de los ReyesKent de los Reyes
24110 bronze badges
24110 bronze badges
add a comment |
add a comment |
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$begingroup$
The last structure does not really exist in slightly acidified solution of the given compound.
$endgroup$
– J_B892
7 hours ago
$begingroup$
Coming to this question won't even cis and trans also contribute to Number of tautomers?
$endgroup$
– J_B892
7 hours ago
$begingroup$
yes I was confused whether last structure is correct or not. but don't know the reason to eliminate it. why it doesn't exist in acidified solution? also if we make the cis and trans structure as well then we will have more than 4 structures which are not in the option. that means the question is just asking the standard structures.
$endgroup$
– Garima Singh
7 hours ago
$begingroup$
Once you do a single tautomerism there's a hydrogen bonding (6 membered ring) formed between -OH and the oxygen. This gives stability to the compound and prefers not to further tautomerise
$endgroup$
– J_B892
7 hours ago