Can you help me with this question from organic chemistry lab? Let me give you information about the lab.

separation of organic substances.

A mixture of three solid organic substances is to be separated by an acid$-$base extraction of a

organic solution. These substances must be used:

Benzoic acid $($acidic compound$)$

$4-$Nitroaniline $($basic compound$)$

Naphthalene $($neutral$)$

All the substances are easily soluble in organic solvents approximately in the middle of the polarity scale, but

not soluble in water. In this assignment, dichloromethane will be used as the organic phase.

Execution:

$$ Weigh out from a finished mixture, about $3$ grams of a $1$:$1$:$1$ mixture of the substances mentioned above.

Record the exact weight.

$$ Dissolve the mixture in approx. $50$ mL of dichloromethane in a beaker and transfer the solution to a

separatory funnel.

$$ Acidic and basic components are then extracted by extracting with basic and respectively

acidic water solution $($use $1$M NaOH or $1$M HCl$).$ Neutral component remains dissolved in organic

phase.

$$ All extractions are done $3$ times with $50$ mL portions each time. The portions are beaten

together in an a flask which is labeled with the substance it contains.

$$ To ensure purity of the water phases, these phases must also be extracted with a little organic

solvent: take the combined acidic water phase in the separatory funnel and extract once with approx

$15$ mL of dichloromethane. This residue is transferred to the organic phase. Do the same

with the overall basic water phase. Wash the combined organic phase with clean

water at the end. All substances are now available in $($hopefully$)$ pure solutions.

$$ The pH is measured in the water solutions and they are neutralized $($NOTE$!6$M NaOH or $6$M HCl$).$ Precipitated

substance is filtered off with suction filtration, dried with a desiccator and weighed.

$$ Yield must be determined by weighing the flask before and after evaporation.

$$ Organic solution is cleaned of water residues by adding a desiccant $($MgSO$4).$

let the solution dry with stirring for $15$ minutes. The desiccant is then filtered off I need help with these two questions:

Which reaction occurs during extraction with alkaline water solution? Please draw the reaction equation with structural formulas and use resonance arrows. $($ organic chemistry$)$

What reaction occurs during extraction with an acidic water solution? draw the reaction equation with structural formulas and use resonance arrows. please draw the way its done in organic chemistry. Thank you for the help.