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Organic Chemistry

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2 Mar 2009 13:02:48 IST

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is chf3 more acidic than chcl3 ?

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is chf3 more acidic than chcl3 ?

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Anthurfa

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2 Mar 2009 14:52:17 IST

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I think chf3 will be more acidic coz the c-h bond is highly polar. This, in turn is bcoz f pulls most of the e density of the c-f bond towards itself makin the carbon e deficient.

arpit rathi

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2 Mar 2009 19:11:00 IST

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i also think it's corrct........he same rason ofcourse

Pallavi Singhal

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2 Mar 2009 19:17:44 IST

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Yup..it is b'coz fluorine is more e.negative than chlorine & hence exhibits more -ve inductive thus producing more +ve charge on carbon & making it electron deficient.......

vignesh the cooler version of newton

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2 Mar 2009 22:13:26 IST

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i think No..CHCl3 is more acidic than CHF3 .... firstly, C-Cl bond is more polar becoz polarization not onl depends on electronegetivity but also bond length

Polarization p = q*2l ( 2l = distance between the point charges)

also, (-):CCl3 anion is stabilised due to back bonding as Cl has vacant d orbital... hence, its hybridization is also sp2 and not sp3......

whereas (-):CF3 anion is not that stable.. plzz correct me if wrong..

Suraj

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2 Mar 2009 23:23:19 IST

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Basicity means the loss of electrons , Lewis bases are electron donors, the basicity of given organic compound is determined on the ability of the compound to loose electrons. Amongst CHCl3 & CHF3, i think the more strong base should be CHCl3 because the bond in it is highly polar & it can break easily than the bond present in CHF3, because F is small in size & has high electronegativity, and large polarising power so the bond can be strong,in the case of F.

Suraj

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2 Mar 2009 23:26:18 IST

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Sahil Gupta

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2 Mar 2009 23:37:45 IST

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CHCl3 in more acidic because the conjugate base is stabilized through back-bonding

rtrikha

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3 Mar 2009 07:32:51 IST

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CHCl3 is more acidic as compared to flouroform i.e. CHF3 this is because apart from the above explanations this can be proved theoretically too

The interaction between CHX₃ (X=F, Cl) and OH⁻ is investigated theoretically.Proton transfer complexes CX₃⁻H₂O are more stable by 1.1 kcal mol⁻¹ (X=F) and 7.1 kcal mol⁻¹ (X=Cl) than the X₃CHOH⁻ complexes. In the X₃CHOH⁻ complexes which are favourable in the separated reactants, strong CHOH⁻ hydrogen bonds, characterized by energies of 25.7 kcal mol⁻¹ (X=F) and 31.8 kcal mol⁻¹ (X=Cl) are formed

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