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![[Post New]](/templates/default/images/icon_minipost_new.gif) 29 Apr 2008 07:21:04 IST
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Which of the following is the strongest acid?
(a) o methoxybenzoic
acid
(b) salicylic acid
(c) 2, 6 dihydroxy
benzoic acid
(d) benzoic acid
Giv reason with ur ans
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It is 2,6-dihydroxybenzoicacid.
It is because of ortho effect(Hope u know ortho effect!).
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"Nenenthedhavano naake teleedu"
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29 Apr 2008 16:33:59 IST
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@Harsha,
I think the ortho effect will not be much pronounced in case of 2,6-dihydroxybenzoic acid.
OH groups are not so bulky so as to rotate the C of COOH to break the resonance.
Its acidity can be explained by the stability of conjugate base. Remove H from COOH and form COO-.
Now due to resonance within the COO- group, this -ve charge will be shared by both Os of COOH and on both sides of COOH there are 2 OH groups means 2 WAY HYDROGEN BONDING. Means conjugate base will be very stable thus contributing to its acidity.
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29 Apr 2008 23:36:12 IST
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yes tarin is right it is indeed hydrogen bonding which is reason
for increased acidity !!!
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30 Apr 2008 10:29:50 IST
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no dude, OH will show considerable ortho effect...i go with harsha's explanation...
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30 Apr 2008 10:35:08 IST
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i belive extensive h bonding after d removal of a proton from -COOH group will stabilize the conjugate base thus it will make 2,6 dihydroxybenzoic acid most acidic
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30 Apr 2008 10:36:34 IST
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Tarin too is right.
Both Ortho effect and Intra molecular H-Bonding are accountable here.
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"Nenenthedhavano naake teleedu"
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30 Apr 2008 11:17:27 IST
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hey guys, are u sure H-bonding will increase acidity...???
I think it will decrease acidity because removable H atom of COOH group will also form H- bond with OH group , so it will be difficult to remove it ....making it less acidic...
pls xplain..
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30 Apr 2008 12:33:30 IST
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The left side ion is more stable and more symmetric than the one on the right.
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