Aromaticity of heterocyclic compound [closed]

The name of the pictureThe name of the pictureThe name of the pictureClash Royale CLAN TAG#URR8PPP











up vote
1
down vote

favorite












This is a question of JAM 2017. According to the answer key the answer is 4. But I found only the last 3 as aromatic . So which one is the 4th aromatic compound? Please explain enter image description here










share|improve this question















closed as off-topic by Nilay Ghosh, Jon Custer, a-cyclohexane-molecule, A.K., Mithoron Sep 3 at 18:50


This question appears to be off-topic. The users who voted to close gave this specific reason:


  • "Homework questions must demonstrate some effort to understand the underlying concepts. For help asking a good homework question, see: How do I ask homework questions on Chemistry Stack Exchange?" – Nilay Ghosh, Jon Custer, a-cyclohexane-molecule, A.K., Mithoron
If this question can be reworded to fit the rules in the help center, please edit the question.








  • 1




    Are you sure about the boron compound?
    – Waylander
    Sep 3 at 9:39











  • No Sir..I was wrong... It's non aromatic.. I got the correct answer . 1,2,4 and 5. @waylander
    – user67074
    Sep 3 at 9:40















up vote
1
down vote

favorite












This is a question of JAM 2017. According to the answer key the answer is 4. But I found only the last 3 as aromatic . So which one is the 4th aromatic compound? Please explain enter image description here










share|improve this question















closed as off-topic by Nilay Ghosh, Jon Custer, a-cyclohexane-molecule, A.K., Mithoron Sep 3 at 18:50


This question appears to be off-topic. The users who voted to close gave this specific reason:


  • "Homework questions must demonstrate some effort to understand the underlying concepts. For help asking a good homework question, see: How do I ask homework questions on Chemistry Stack Exchange?" – Nilay Ghosh, Jon Custer, a-cyclohexane-molecule, A.K., Mithoron
If this question can be reworded to fit the rules in the help center, please edit the question.








  • 1




    Are you sure about the boron compound?
    – Waylander
    Sep 3 at 9:39











  • No Sir..I was wrong... It's non aromatic.. I got the correct answer . 1,2,4 and 5. @waylander
    – user67074
    Sep 3 at 9:40













up vote
1
down vote

favorite









up vote
1
down vote

favorite











This is a question of JAM 2017. According to the answer key the answer is 4. But I found only the last 3 as aromatic . So which one is the 4th aromatic compound? Please explain enter image description here










share|improve this question















This is a question of JAM 2017. According to the answer key the answer is 4. But I found only the last 3 as aromatic . So which one is the 4th aromatic compound? Please explain enter image description here







organic-chemistry heterocyclic-compounds aromaticity






share|improve this question















share|improve this question













share|improve this question




share|improve this question








edited Sep 3 at 11:00









Abcd

2,2003829




2,2003829










asked Sep 3 at 5:16









user67074

412




412




closed as off-topic by Nilay Ghosh, Jon Custer, a-cyclohexane-molecule, A.K., Mithoron Sep 3 at 18:50


This question appears to be off-topic. The users who voted to close gave this specific reason:


  • "Homework questions must demonstrate some effort to understand the underlying concepts. For help asking a good homework question, see: How do I ask homework questions on Chemistry Stack Exchange?" – Nilay Ghosh, Jon Custer, a-cyclohexane-molecule, A.K., Mithoron
If this question can be reworded to fit the rules in the help center, please edit the question.




closed as off-topic by Nilay Ghosh, Jon Custer, a-cyclohexane-molecule, A.K., Mithoron Sep 3 at 18:50


This question appears to be off-topic. The users who voted to close gave this specific reason:


  • "Homework questions must demonstrate some effort to understand the underlying concepts. For help asking a good homework question, see: How do I ask homework questions on Chemistry Stack Exchange?" – Nilay Ghosh, Jon Custer, a-cyclohexane-molecule, A.K., Mithoron
If this question can be reworded to fit the rules in the help center, please edit the question.







  • 1




    Are you sure about the boron compound?
    – Waylander
    Sep 3 at 9:39











  • No Sir..I was wrong... It's non aromatic.. I got the correct answer . 1,2,4 and 5. @waylander
    – user67074
    Sep 3 at 9:40













  • 1




    Are you sure about the boron compound?
    – Waylander
    Sep 3 at 9:39











  • No Sir..I was wrong... It's non aromatic.. I got the correct answer . 1,2,4 and 5. @waylander
    – user67074
    Sep 3 at 9:40








1




1




Are you sure about the boron compound?
– Waylander
Sep 3 at 9:39





Are you sure about the boron compound?
– Waylander
Sep 3 at 9:39













No Sir..I was wrong... It's non aromatic.. I got the correct answer . 1,2,4 and 5. @waylander
– user67074
Sep 3 at 9:40





No Sir..I was wrong... It's non aromatic.. I got the correct answer . 1,2,4 and 5. @waylander
– user67074
Sep 3 at 9:40











1 Answer
1






active

oldest

votes

















up vote
5
down vote













Actually not all of the last three are aromatic. Look carefully at the third compound; the heteroatom is boron, not nitrogen, and so does not contribute the electron pair that would be needed to make six pi electrons in an aromatic ring. That compound is instead antiaromatic.



So JAM 2017 is apparently rendering both of the first two compounds as aromatic. This, however, is dubious. The first compound in the list is a pyrone, which not everyone would call aromatic. To make an aromatic contributing structure in pyrone we would have to render the carbonyl group as its zwitterionic structure ($ceC^+-O^-$) and then distribute the positive charge around the ring which has an electronegative oxygen atom. We'd have to weigh the favorable effect of aromaticity against the unfavorable effect of putting a positive charge into an electronegative ring.



As for the second compound, we would need to "polarize" two carbonyl groups and concentrate two positive charges into the small ring, and that is not happening even with aromaticity. There is a saving grace, however: if the $ceN-H$ protons are tautomerized onto the oxygen atoms, converting the "keto" structure to its "enol" form, then the tautomerized molecule is 2,4-dihydroxy-1,3-diazine, which would be unambiguously aromatic.



What it boils down to is that aromaticity is often not the simple yes/no question often suggested in introductory chemistry texts. Given this ambiguity, one could potentially defend an answer of 2, 3, or 4 (but not the last three for the two larger numbers) to the JAM 2017 question.






share|improve this answer




















  • Actually in keto form of uracil it's maybe second most important mesomeric structure is the one with + on nitrogens and is aromatic.
    – Mithoron
    Sep 3 at 19:04










  • Curious about the source. Wikipedia does not refer to a carbonyl polarized structure (but does indicate that both tautomerization and stability of the given structure without Huckel aromaticity occur).
    – Oscar Lanzi
    Sep 3 at 19:17










  • Meh, it's standard "amidic" stabilisation, but it does lead to aromatic mesomeric structures. also even full 2+ charge on aromatic cycles is possible. Ron made an answer about it, mayybe wold findd it...
    – Mithoron
    Sep 3 at 19:32










  • chemistry.stackexchange.com/questions/28882/…
    – Mithoron
    Sep 3 at 19:46

















1 Answer
1






active

oldest

votes








1 Answer
1






active

oldest

votes









active

oldest

votes






active

oldest

votes








up vote
5
down vote













Actually not all of the last three are aromatic. Look carefully at the third compound; the heteroatom is boron, not nitrogen, and so does not contribute the electron pair that would be needed to make six pi electrons in an aromatic ring. That compound is instead antiaromatic.



So JAM 2017 is apparently rendering both of the first two compounds as aromatic. This, however, is dubious. The first compound in the list is a pyrone, which not everyone would call aromatic. To make an aromatic contributing structure in pyrone we would have to render the carbonyl group as its zwitterionic structure ($ceC^+-O^-$) and then distribute the positive charge around the ring which has an electronegative oxygen atom. We'd have to weigh the favorable effect of aromaticity against the unfavorable effect of putting a positive charge into an electronegative ring.



As for the second compound, we would need to "polarize" two carbonyl groups and concentrate two positive charges into the small ring, and that is not happening even with aromaticity. There is a saving grace, however: if the $ceN-H$ protons are tautomerized onto the oxygen atoms, converting the "keto" structure to its "enol" form, then the tautomerized molecule is 2,4-dihydroxy-1,3-diazine, which would be unambiguously aromatic.



What it boils down to is that aromaticity is often not the simple yes/no question often suggested in introductory chemistry texts. Given this ambiguity, one could potentially defend an answer of 2, 3, or 4 (but not the last three for the two larger numbers) to the JAM 2017 question.






share|improve this answer




















  • Actually in keto form of uracil it's maybe second most important mesomeric structure is the one with + on nitrogens and is aromatic.
    – Mithoron
    Sep 3 at 19:04










  • Curious about the source. Wikipedia does not refer to a carbonyl polarized structure (but does indicate that both tautomerization and stability of the given structure without Huckel aromaticity occur).
    – Oscar Lanzi
    Sep 3 at 19:17










  • Meh, it's standard "amidic" stabilisation, but it does lead to aromatic mesomeric structures. also even full 2+ charge on aromatic cycles is possible. Ron made an answer about it, mayybe wold findd it...
    – Mithoron
    Sep 3 at 19:32










  • chemistry.stackexchange.com/questions/28882/…
    – Mithoron
    Sep 3 at 19:46














up vote
5
down vote













Actually not all of the last three are aromatic. Look carefully at the third compound; the heteroatom is boron, not nitrogen, and so does not contribute the electron pair that would be needed to make six pi electrons in an aromatic ring. That compound is instead antiaromatic.



So JAM 2017 is apparently rendering both of the first two compounds as aromatic. This, however, is dubious. The first compound in the list is a pyrone, which not everyone would call aromatic. To make an aromatic contributing structure in pyrone we would have to render the carbonyl group as its zwitterionic structure ($ceC^+-O^-$) and then distribute the positive charge around the ring which has an electronegative oxygen atom. We'd have to weigh the favorable effect of aromaticity against the unfavorable effect of putting a positive charge into an electronegative ring.



As for the second compound, we would need to "polarize" two carbonyl groups and concentrate two positive charges into the small ring, and that is not happening even with aromaticity. There is a saving grace, however: if the $ceN-H$ protons are tautomerized onto the oxygen atoms, converting the "keto" structure to its "enol" form, then the tautomerized molecule is 2,4-dihydroxy-1,3-diazine, which would be unambiguously aromatic.



What it boils down to is that aromaticity is often not the simple yes/no question often suggested in introductory chemistry texts. Given this ambiguity, one could potentially defend an answer of 2, 3, or 4 (but not the last three for the two larger numbers) to the JAM 2017 question.






share|improve this answer




















  • Actually in keto form of uracil it's maybe second most important mesomeric structure is the one with + on nitrogens and is aromatic.
    – Mithoron
    Sep 3 at 19:04










  • Curious about the source. Wikipedia does not refer to a carbonyl polarized structure (but does indicate that both tautomerization and stability of the given structure without Huckel aromaticity occur).
    – Oscar Lanzi
    Sep 3 at 19:17










  • Meh, it's standard "amidic" stabilisation, but it does lead to aromatic mesomeric structures. also even full 2+ charge on aromatic cycles is possible. Ron made an answer about it, mayybe wold findd it...
    – Mithoron
    Sep 3 at 19:32










  • chemistry.stackexchange.com/questions/28882/…
    – Mithoron
    Sep 3 at 19:46












up vote
5
down vote










up vote
5
down vote









Actually not all of the last three are aromatic. Look carefully at the third compound; the heteroatom is boron, not nitrogen, and so does not contribute the electron pair that would be needed to make six pi electrons in an aromatic ring. That compound is instead antiaromatic.



So JAM 2017 is apparently rendering both of the first two compounds as aromatic. This, however, is dubious. The first compound in the list is a pyrone, which not everyone would call aromatic. To make an aromatic contributing structure in pyrone we would have to render the carbonyl group as its zwitterionic structure ($ceC^+-O^-$) and then distribute the positive charge around the ring which has an electronegative oxygen atom. We'd have to weigh the favorable effect of aromaticity against the unfavorable effect of putting a positive charge into an electronegative ring.



As for the second compound, we would need to "polarize" two carbonyl groups and concentrate two positive charges into the small ring, and that is not happening even with aromaticity. There is a saving grace, however: if the $ceN-H$ protons are tautomerized onto the oxygen atoms, converting the "keto" structure to its "enol" form, then the tautomerized molecule is 2,4-dihydroxy-1,3-diazine, which would be unambiguously aromatic.



What it boils down to is that aromaticity is often not the simple yes/no question often suggested in introductory chemistry texts. Given this ambiguity, one could potentially defend an answer of 2, 3, or 4 (but not the last three for the two larger numbers) to the JAM 2017 question.






share|improve this answer












Actually not all of the last three are aromatic. Look carefully at the third compound; the heteroatom is boron, not nitrogen, and so does not contribute the electron pair that would be needed to make six pi electrons in an aromatic ring. That compound is instead antiaromatic.



So JAM 2017 is apparently rendering both of the first two compounds as aromatic. This, however, is dubious. The first compound in the list is a pyrone, which not everyone would call aromatic. To make an aromatic contributing structure in pyrone we would have to render the carbonyl group as its zwitterionic structure ($ceC^+-O^-$) and then distribute the positive charge around the ring which has an electronegative oxygen atom. We'd have to weigh the favorable effect of aromaticity against the unfavorable effect of putting a positive charge into an electronegative ring.



As for the second compound, we would need to "polarize" two carbonyl groups and concentrate two positive charges into the small ring, and that is not happening even with aromaticity. There is a saving grace, however: if the $ceN-H$ protons are tautomerized onto the oxygen atoms, converting the "keto" structure to its "enol" form, then the tautomerized molecule is 2,4-dihydroxy-1,3-diazine, which would be unambiguously aromatic.



What it boils down to is that aromaticity is often not the simple yes/no question often suggested in introductory chemistry texts. Given this ambiguity, one could potentially defend an answer of 2, 3, or 4 (but not the last three for the two larger numbers) to the JAM 2017 question.







share|improve this answer












share|improve this answer



share|improve this answer










answered Sep 3 at 9:45









Oscar Lanzi

13.1k12444




13.1k12444











  • Actually in keto form of uracil it's maybe second most important mesomeric structure is the one with + on nitrogens and is aromatic.
    – Mithoron
    Sep 3 at 19:04










  • Curious about the source. Wikipedia does not refer to a carbonyl polarized structure (but does indicate that both tautomerization and stability of the given structure without Huckel aromaticity occur).
    – Oscar Lanzi
    Sep 3 at 19:17










  • Meh, it's standard "amidic" stabilisation, but it does lead to aromatic mesomeric structures. also even full 2+ charge on aromatic cycles is possible. Ron made an answer about it, mayybe wold findd it...
    – Mithoron
    Sep 3 at 19:32










  • chemistry.stackexchange.com/questions/28882/…
    – Mithoron
    Sep 3 at 19:46
















  • Actually in keto form of uracil it's maybe second most important mesomeric structure is the one with + on nitrogens and is aromatic.
    – Mithoron
    Sep 3 at 19:04










  • Curious about the source. Wikipedia does not refer to a carbonyl polarized structure (but does indicate that both tautomerization and stability of the given structure without Huckel aromaticity occur).
    – Oscar Lanzi
    Sep 3 at 19:17










  • Meh, it's standard "amidic" stabilisation, but it does lead to aromatic mesomeric structures. also even full 2+ charge on aromatic cycles is possible. Ron made an answer about it, mayybe wold findd it...
    – Mithoron
    Sep 3 at 19:32










  • chemistry.stackexchange.com/questions/28882/…
    – Mithoron
    Sep 3 at 19:46















Actually in keto form of uracil it's maybe second most important mesomeric structure is the one with + on nitrogens and is aromatic.
– Mithoron
Sep 3 at 19:04




Actually in keto form of uracil it's maybe second most important mesomeric structure is the one with + on nitrogens and is aromatic.
– Mithoron
Sep 3 at 19:04












Curious about the source. Wikipedia does not refer to a carbonyl polarized structure (but does indicate that both tautomerization and stability of the given structure without Huckel aromaticity occur).
– Oscar Lanzi
Sep 3 at 19:17




Curious about the source. Wikipedia does not refer to a carbonyl polarized structure (but does indicate that both tautomerization and stability of the given structure without Huckel aromaticity occur).
– Oscar Lanzi
Sep 3 at 19:17












Meh, it's standard "amidic" stabilisation, but it does lead to aromatic mesomeric structures. also even full 2+ charge on aromatic cycles is possible. Ron made an answer about it, mayybe wold findd it...
– Mithoron
Sep 3 at 19:32




Meh, it's standard "amidic" stabilisation, but it does lead to aromatic mesomeric structures. also even full 2+ charge on aromatic cycles is possible. Ron made an answer about it, mayybe wold findd it...
– Mithoron
Sep 3 at 19:32












chemistry.stackexchange.com/questions/28882/…
– Mithoron
Sep 3 at 19:46




chemistry.stackexchange.com/questions/28882/…
– Mithoron
Sep 3 at 19:46


Popular posts from this blog

How to check contact read email or not when send email to Individual?

Displaying single band from multi-band raster using QGIS

How many registers does an x86_64 CPU actually have?