Why is chloro acetic acid stronger than acetic acid?

Answer 1

Actually, benzoic acid is the stronger acid when compared to ethanoic acid.

This is due to the delocalisation of the lone pair of electrons on the oxygen atom into the benzene, increasing the polarity of the -OH bond and thus makes the cleaving of the H+ ion easier. The delocalisation of electrons into the benzene ring also stabilises the carboxylate ion. Therefore the position of equilibrium lies more to the right and this shows that benzoic is a more acidic acid.

The simplified version is that a benzene ring is electron withdrawing and a methyl group is electron releasing. The electron withdrawing power makes the releasing of the H+ ion easier.

Answer 2

As we know that acetic acid is CH3 substituted formic acid .since CH3 is an electron donating relative to hydrogen .so, it donates the electron to carboxyl group and makes it more negative.

this phenomenon makes acetic acid weaker acid than formic acid .Thus formic acid is stronger acid than acetic acid.

Written by Mayank shekhar

"student of ISc {PCM}

R.L.S.Y college ,Magadh university ,bodh gaya ,Bihar

Answer 3

the important factor effecting the acidity is inductive effect of substituents on the alpha carbon.

this can be represented by:

1-electron releasing alkylgroup decrease the acidity:-

this increase negative charge on carboxylic ion and destabilize it.the loss of proton becomes more difficult also the size of alkyl group increases,acidity decreases such as proponic acid because it contains 3 carbons atoms while in acetic acid there are 2 carbon atoms so it has more acidity

Answer 4

Due to - i effect of chlorine atom chloroacetic acid is stronger than acetic acid as conjugate base chloroacetate is much stable than acetate anion. For the presence of 3 chlorine atom trichloroacetic acid is stronger than chloroacetic acid

Answer 5

Propionic acid is slightly weaker than acetic acid because of the additional delocalization of electrons in the longer alkane chain on propionic acid, versus just the end methyl group adjacent to the carboxyl group on acetic acid.

Greater delocalization on the opposite side of the carbonyl group in propionic acid creates a weaker dipole moment on the C-O bond of the carbonyl group, which results in a slightly stronger O-H bond, resulting in less dissociation of the COOH proton.

The ratio of dissociated (propionate + proton) to propionic acid makes propionic acid slightly weaker than acetic acid.

Answer 6

Chloroacetic acid is stronger, because it contains (more electronegative) chlorine atoms in the place of (less electronegative) hydrogen atoms.

Answer 7

Short answer: b/c water allows easier hydrogen bonding while methanol does not.

Answer 8

Acetic acid will dissociate more in water than in methanol. Hence acetic acid is relatively more acidic in water than in methanol.