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Shweta Thakur posted an Question

December 23, 2020 • 00:12 am

30 points

IIT JAM
Chemistry (CY)

Pyrrolidines and piperidines which is more basic....??

pyrrolidines and piperidines which is more basic....??

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Dinesh khalmaniya 1

https://chemistry.stackexchange.com/questions/48128/which-is-more-basic-piperidine-or-pyrrolidine-and-why
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Priyanshu kumar Best Answer

pyrrolidine is slightly more basic They have almost same basicity..The pka value of pyrrolidine is about 11.27 while that of piperidine is 11.24..We know that larger the pka value of the conjugate acid of the base,higher is the basicity. Pyrrolidine is a fully reduced pyrrole and piperidine is a fully reduced pyridine. Now pyrrolidine has a five membered ring while piperidine has a six membered ring. Apparently pyrrolidine gains a touch more conformational stabilization after protonation due to its five membered ring and we know that a five membered ring is more stable than a six membered ring. Hence the conjugate acid of pyrrolidine is slightly more stabilized over piperidine and hence pyrrolidine has a slightly higher basicity over piperidine
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https://socratic.org/questions/basic-order#:~:text=Hardly%20any%20difference...%20but,a%20of%20piperidine%20is%2011.22%20. check this
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sir five membered ring stable kyin hota hai six membered se
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six membered Jada hona chahiye because strain less hota
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in case of heterocyclic 5 membered more stable...in general 6 membered more stable
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thanku sir
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five membered heterocyclic ring is more stable it has more aromatic property than six membered heterocyclic ring because of the heteroatom.
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