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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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2

1

$begingroup$

The answer for the above question is 3. But I am able to draw 4 structures:

Where am I getting wrong?

tautomer

share|improve this question

edited 6 hours ago

Loong♦

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asked 8 hours ago

Garima SinghGarima Singh

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$endgroup$

• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  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 | 

2

1

$begingroup$

The answer for the above question is 3. But I am able to draw 4 structures:

Where am I getting wrong?

tautomer

share|improve this question

edited 6 hours ago

Loong♦

37.1k99 gold badges9292 silver badges196196 bronze badges

asked 8 hours ago

Garima SinghGarima Singh

8333 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

share|improve this question

edited 6 hours ago

Loong♦

37.1k99 gold badges9292 silver badges196196 bronze badges

asked 8 hours ago

Garima SinghGarima Singh

8333 bronze badges

$endgroup$

share|improve this question

edited 6 hours ago

Loong♦

37.1k99 gold badges9292 silver badges196196 bronze badges

asked 8 hours ago

Garima SinghGarima Singh

8333 bronze badges

share|improve this question

edited 6 hours ago

Loong♦

37.1k99 gold badges9292 silver badges196196 bronze badges

asked 8 hours ago

Garima SinghGarima Singh

8333 bronze badges

edited 6 hours ago

Loong♦

37.1k99 gold badges9292 silver badges196196 bronze badges

edited 6 hours ago

Loong♦

37.1k99 gold badges9292 silver badges196196 bronze badges

asked 8 hours ago

Garima SinghGarima Singh

8333 bronze badges

asked 8 hours ago

Garima SinghGarima Singh

8333 bronze badges

2 Answers
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3

$begingroup$

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!

share|improve this answer

answered 6 hours ago

J_B892J_B892

46344 silver badges1717 bronze badges

$endgroup$

add a comment | 

0

$begingroup$

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.

share|improve this answer

answered 5 hours ago

Kent de los ReyesKent de los Reyes

2411010 bronze badges

$endgroup$

add a comment | 

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3

$begingroup$

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!

share|improve this answer

answered 6 hours ago

J_B892J_B892

46344 silver badges1717 bronze badges

$endgroup$

add a comment | 

3

$begingroup$

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!

share|improve this answer

answered 6 hours ago

J_B892J_B892

46344 silver badges1717 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!

share|improve this answer

answered 6 hours ago

J_B892J_B892

46344 silver badges1717 bronze badges

$endgroup$

share|improve this answer

answered 6 hours ago

J_B892J_B892

46344 silver badges1717 bronze badges

answered 6 hours ago

J_B892J_B892

46344 silver badges1717 bronze badges

answered 6 hours ago

J_B892J_B892

46344 silver badges1717 bronze badges

0

$begingroup$

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.

share|improve this answer

answered 5 hours ago

Kent de los ReyesKent de los Reyes

2411010 bronze badges

$endgroup$

add a comment | 

0

$begingroup$

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.

share|improve this answer

answered 5 hours ago

Kent de los ReyesKent de los Reyes

2411010 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.

share|improve this answer

answered 5 hours ago

Kent de los ReyesKent de los Reyes

2411010 bronze badges

$endgroup$

share|improve this answer

answered 5 hours ago

Kent de los ReyesKent de los Reyes

2411010 bronze badges

answered 5 hours ago

Kent de los ReyesKent de los Reyes

2411010 bronze badges

answered 5 hours ago

Kent de los ReyesKent de los Reyes

2411010 bronze badges