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Reshav posted an Question
October 28, 2020 • 02:25 am 30 points
  • IIT JAM
  • Chemistry (CY)

Is it the correct order for acidity and if not then what will be the correct order of acidity explain with reason?

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  • Narayanarao gundoju

    it is correct order of acidity reason is -i effect of halogens more acidic when strong -i effect incase of C-F loan pair donate to ring C due to same energy level so here -i effect and +M effect also present

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    Dinesh khalmaniya 1 best-answer

    Acidity order of 4-halophenols parafluorophenol (9.92) parachlorophenol (9.41) parabromophenol (9.17) paraiodophenol (9.30) Experimental acidic strength order: parabromophenol > paraiodophenol > parachlorophenol > parafluorophenol

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    For 4-fluorophenol, the +R effect of FF is significant but weaker than -I effect. The electron pair on the 2p2p orbitals of FF can easily delocalise with the benzene ring because of the stronger 2pπ-2pπ2pπ-2pπ overlap, which makes +R+R effect significant . That's why it increases the electron density on the carbon near the −OH−OH group to such an extent which decreases its ability to donate protons, greatly decreasing its acidity. Considering intermolecular hydrogen bonding also, the acidity of the compound decreases further due to strongest intermolecular hydrogen bonding between the halogens. For 4-chlorophenol, the +R effect is negligible due to much weaker 3pπ-2pπ3pπ-2pπ overlap and thus the −I−I effect becomes more prominent. But ClCl is electronegative enough to form strong intermolecular hydrogen bonding(HO−C6H4−Cl⋅⋅⋅H−O−C6H4−Cl⋅⋅⋅)HO−CX6HX4−Cl⋅⋅⋅H−O−CX6HX4−Cl⋅⋅⋅). That's why, it becomes difficult to remove hydrogen atoms from −OH−OH group, decreasing its acidity. For 4-bromophenol and 4-iodophenol, there is no strong hydrogen bonding due to much less electronegative BrBr and II atoms, and also +R effect is ineffective due to very weak 4pπ-2pπ4pπ-2pπ and 5pπ-2pπ5pπ-2pπ overlap. Only -I effect is acing for these two compounds in favour of acidity. As -I effect of BrBr is larger than II, the acidity of p-bromophenol is greater than the p-iodophenol.

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    Priyanshu kumar best-answer

    check explanation reshav

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    parabromophenol > paraiodophenol > parachlorophenol > parafluorophenol

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    sir i think this is not the correct order

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    because fluorine ka +R lg to skta hai but yha kese lgega kisi ke bhi vacant orbital hoga hi nhi to kis bat ka +R

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    sir is question ke answers me bhut variations hai hr jgh

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    see pka value

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    teacher kuch aur order btate hai iska and books me kuch aur order likha hai iska

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    okk wait let me verify

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    reshav this is correct order

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    sir check my explanation is this correct

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    reshav acidity experimentally determined hote hai...or pka value ye suggest nhi kr rha hai

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    Br or iodine ke case me backbonding nhi hai isiliye only -I effect honge...or bromine ke -I jyada hote hai iodine se...so 3>4>2>1 honge

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