- #1
PFuser1232
- 479
- 20
According to my A level Chemistry textbook, the presence of the O atom in a C=O bond in any carboxylic acid (CH3COOH, for instance) pulls the electrons towards it causing the O-H bond to "weaken", thereby making the molecule more susceptible to dissociation, or in other words, accounts for the "acidity" of carboxylic acids.
If i am not wrong, the act of pulling electrons away from the O-H bond would give rise to an even more polar O-H bond. What eludes me is how this accounts for a decrease in bond energy. As a matter of fact, when I apply the somewhat simple (considering the number of variables involved in such a situation) case of Coulomb's law for two point charges, it appears to me this separation of charges would make the bond all the stronger.
Can someone please point out to me where I'm going wrong with this? Perhaps the O-H bond does become stronger as a result of the negative inductive effect mentioned earlier in the post, but becomes more prone to the tendency of H2O to separate cations and anions? So the bond doesn't become weaker per se, and just becomes more "prone to dissociation"? I am lost.
If i am not wrong, the act of pulling electrons away from the O-H bond would give rise to an even more polar O-H bond. What eludes me is how this accounts for a decrease in bond energy. As a matter of fact, when I apply the somewhat simple (considering the number of variables involved in such a situation) case of Coulomb's law for two point charges, it appears to me this separation of charges would make the bond all the stronger.
Can someone please point out to me where I'm going wrong with this? Perhaps the O-H bond does become stronger as a result of the negative inductive effect mentioned earlier in the post, but becomes more prone to the tendency of H2O to separate cations and anions? So the bond doesn't become weaker per se, and just becomes more "prone to dissociation"? I am lost.