Question

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Answer 1

chlorine shows +R and -I effects. Due to ortho effect anything at ortho would be more acidic. Now +R pronounced at ortho and para position but due to special ortho effect, ortho one is most acidic now left with meta. In meta there is no R+ effect (see there resonance structures ) so only -I effect left so order is ortho>meta now effectively electrons are withdrawn so far so both of them have to be more acidic than benzoic acid but in case of para, +R is dominating over -I also because -I is distance dependent. so net effect being +R which will make even benzoic acid more acidic than para one.

so as far as i think
the order will be

ortho>meta>benzoic acid> para.


hope it helps you

Answer 2

HELLO THERE!

We have four compounds, whose acidic order is to be determined. Let's check them out, one by one:

(a) Meta-chloro benzoic acid.

(b) Ortho-chloro benzoic acid.

(c) Para-chloro benzoic acid.

(d) Benzoic acid.

Now, we know, that if any group is attached in the ortho-position, due to ortho effect, that very compound stands first if acidic order is to be determined. So, (b) Ortho-chloro benzoic acid is the most acidic among the four.

Also, in (d) Benzoic acid, there is no group attached in any position of the benzene ring, hence no factor to increase it's acidic strength. So, it stands last in the acidic order.

The competition, now is between m-chloro benzoic acid and p-chloro benzoic acid.

To determine this, we need to know what type of group is -COOH (ortho-para directing or meta directing). Check out the resonating structures of Benzoic acid, in the attachment! A meta-directing group is more acidic if a more eletronegative group is attached to its meta position, as the -I effect comes into play.

From the attachment, it is clear, that negative charge is developed on meta position, so COOH group is meta-directing for electrophilic substitution.

So, from here, we can say that meta-chloro benzoic acid is more acidic than para-chloro benzoic acid.

[Note: If, instead of COOH, OH group was attached and then the acidity order was asked, then the acidity of para-chloro phenol would have been greater than the acidity of meta-chloro phenol, as phenol is o-p directing for electrophilic substitution.]

So, the final order is:

O-chloro benzoic acid > M-chloro benzoic acid > P-chloro benzoic acid > Benzoic acid.

(b) > (a) > (c) > (d).

THANKS!