Order of acidity of substituted benzoic acids and basicity of substituted Aniline

Question

Could you please provide me the reasons for the unusual order of acidity of the following compounds?

ACIDITY

1.HYDROXYPHENOL = m > o > p > Phenol

2. AMINOPHENOL = o > m > phenol > p

3. FLUROPHENOL = o > m > p > phenol ( Here, especially, how can ortho be most acidic when there will be high +M effect of fluorine ??)

4. AMINOBENZOIC ACID = Benzoic Acid > m > p > o ( Why is ortho effect not applicable here )?

and basicity...

BASICITY

1. PHENYLENE DIAMINE = p > m > Aniline > o

Answer 1

Acid base reactions are reversible and thus determined by the stability of the final product. Since the double bond would form on the Flourine, the ortho Hydrogen is the most acidic, as per the Zaitsev rule. There's an exception when using bases such as LDA, which is irreversible and thus kinetically (not thermodynamically) driven.