Free radical addition

Carbene addition

Electrophilic addition

Nucleophilic addition

9.2, 4.7, 16.0

4.8, 9.3, 10.8

7.2, 3.7, 3.2

2.2, 2.3, 3.8

RCOO⁻ > HS⁻ > RCOOH > ROH

HS⁻ > RCOO⁻ > RCOOH > ROH

HS⁻ > RCOO⁻ > ROH > RCOOH

RCOO⁻ > HS⁻ > ROH > RCOOH

Strong mesomeric effect

Hyperconjugative effect

Inductive effect only

Hydrogen bonding

Phenol

o−fluorophenol

m−fluorophenol

p−fluorophenol