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Organic Chemistry

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27 Jan 2009 19:03:53 IST
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Order of acidic behaviour? benzoic acid,o-, m-, and p- methyl derivatives of benzoic acid.
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Order of acidic behaviour? benzoic acid,o-, m-, and p- methyl derivatives of benzoic acid.


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rafa in revival mode's Avatar

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27 Jan 2009 19:20:57 IST
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i think the order should be (1)p(2)m(3)p bcoz the ch3- group increases the electron on the benzene ring and ultimately electron density increases on the oxygen from which h is lost and carboxylate ion is destablised.as the + inductive effect decreases with increasing size so ortho one is most destablised.do correct me if i am wrong.

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27 Jan 2009 19:23:42 IST
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o>p>m
rafa in revival mode's Avatar

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27 Jan 2009 19:33:37 IST
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sorry there is a mistake p>m>o
rafa in revival mode's Avatar

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27 Jan 2009 19:34:17 IST
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prashant please send me the reason.
A$PIRing  HiGh - dEv aDitYa's Avatar

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27 Jan 2009 19:43:32 IST
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In TATA McGRAW-HILL'S Organic Chemistry, it is giveno>m>p.Please anyone explain...!!!!!
palli kartik's Avatar

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27 Jan 2009 19:46:43 IST
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i think the answer given is wrong...............

i referred arihant-it's given p>o>m

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27 Jan 2009 19:52:37 IST
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Ortho is the strongest due to Ortho effectthen para by obvious reasons of stable carbocationthen meta.
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27 Jan 2009 20:01:39 IST
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@10904him, In the TMH book, o- is given highest acidic due to ortho effect, but how is meta > para given?
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27 Jan 2009 21:29:27 IST
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the correct order is o- > m- > p- . Note that o- is stronger than benzoic acid, but rest two are weaker than it. o- group is stronger due to more stable carboxylate ion which is due to resonance aided by intramolecular H-bonding(ortho effect).

Now, when u draw the resonance structures of the carboxylate ion u will find that the o- and p- positions are electron deficient with respect to the p- position due to resonance. Presence of a methyl group will have +I effect and hence reduce the electropositivity of the carbon atom at the p- postion. This will hinder the process of resonance and the corresponding ion becomes less stable. in case of o- position this effect is more than neutralised by ortho-effect.

 

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debmalya choudhuri's Avatar

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27 Jan 2009 22:19:45 IST
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no it is o>m>p due to ortho effect im sure abt this
prashant's Avatar

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28 Jan 2009 19:27:11 IST
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the correct answer is o>m>p . the reason is that the ortho substituted benzoic acid are more acidic than meta and para due to steric factor and for meta and para form their conjugate acid and u will find the reason



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