Answer:
See explanation below
Step-by-step explanation:
To do aflow diagram for extraction of these two components of a sample, we need to analize both reagents so we can make a great diagram and separate both reagents.
First, let's see the acid. The 2-chlorobenzoic acid is a relativel strong acid, so, in order to separate this from a sample we need to use a base to do so. However, it's very important the use of the base here, we cannot use any base to do it, for the main reason that the sample has other component, and this component may react too with the base and the separation will not be succesfull. So, as the chlorobenzoic acid is a relatively strong acid, if we use a strong base such as NaOH, this will react with the acid, but it will also react with the 1,4-dichlorobenzene forming a Sn2 product and a salt like this.
C₆H₄Cl₂ + NaOH ---------> C₆H₅OCl + NaCl
This is the reason which we cannot use NaOH, because it's a strong base that may react with other compounds in the sample.
To solve this, we can use a weak base such as NaHCO₃. This weak base has the strength enough to react with the benzoic acid, but not strong enough to react with the dichlorobenzene.
So, the first step is dissolve the sample in an organic solvent like ether. The next step is mixing the sample with NaHCO₃. This will cause the layer to divide into two layers. One aqueous layer that will have the product of the acid with the base, and an organic layer with the dichlobenzene. Afterward, we just need to use a strong acid like HCl, but dilluted in the aqueous layer to regenerate the acid, and in the organic layer, just heat the solution til the whole solvent evaporates completely.
The flow diagram is below in the attached picture.