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dev_22oct (1326)

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Q4) Which of these is/are aromatic: Pyrrole, Protonated Pyrrole. Give reasons to support our answer ?
    
sandeepramesh (1090)

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pyrrole is aromatic because the lp on N is involved in resonance with the ring making it a 6 en system (4n+2) Huckel rule
 
protonated pyrrole isnt aromatic bcos there is no lp on N hence its a 4 en systen n is hence antiaromatic  
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supralara (63)

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thats right
pyrole is aromatic
and its pronated species is not

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supralara (63)

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4n+2 huckel rule as rohit says
 
moreover the abs of lone pair in protonated species

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<TR><TD>


<DIV ALIGN="right">Glitter Graphics</DIV></TD></TR></TABLE>
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sandeepramesh (1090)

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my name is sandeep ramesh Huh? Who are you? A known friend?
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supralara (63)

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orp

<TABLE CELLSPACING="1" CELLPADDING="1" BORDER="0">
<TR><TD>


<DIV ALIGN="right">Glitter Graphics</DIV></TD></TR></TABLE>
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sandeepramesh (1090)

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are you sure?
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supralara (63)

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check ur nudgebook

<TABLE CELLSPACING="1" CELLPADDING="1" BORDER="0">
<TR><TD>


<DIV ALIGN="right">Glitter Graphics</DIV></TD></TR></TABLE>
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shubham_sachdeva (1793)

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rightly said....pyrrole is aromatic as N -lone pair of electrons are present in unhybridised orbital.so contribute towards aromaticity.n= 1
while protonated is not...

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tarinbansal (2432)

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Pyrrole is aromatic.

The pyrrole N atom is sp2 hybridised and its unhybridised p-orbital overlaps with the p-orbitals of the C atoms to form a continuous ring.

Whereas in protonated pyrrole, this N lone pair is now involved in bonding with H and not available for overlapping.

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dev_22oct (1326)

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good!!
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layman (148)

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But pyrolle doesn't get protonated easily for info. But still hypothetically that's right protonated version is non-arromatic.



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computer001 (1622)

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isnt protonated pyrrole anti-aromatic??
cuz layman says non-aromatic..
it makes a diff if im not wrong..

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layman (148)

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No it is also not antiarromatic because for anti arromatic shifts to take place(HOMO-LUMO and LUMO-HOMO) it should pass thro the Nitrogen which is not possible. So its just conjugated.



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