Question

Arrange these compounds from most acidic through neutral to most basic. NH2 OH NH2 он OH OH a) b) d) e) f) g) < < Acidic Neutral Basic

Answer 1

As shown in the above figure

ortho flourine substituted benzoic acid is the most acidic of all as the ortho substitutions increase the proton abstraction

benzoic acid stands the second position

ortho substituted phenol is less acidic than but its acidity is contributed by the resonance which helps in the proton release

ortho substituted cyclohexanol is the least acidic of all the above

ortho substituted aniline is the least basic as the lone pair on nitrogen takes part in the resonance and not in the donation

phenylethylamine stands next as it has its lone pair of electrons for donation and does not take part in resonance

finally most basic is the methyl substituted cyclohexylamine as it has its lone pairs for donation as well as the +I effect of methyl; groups increases the electron density over nitrogen such that it can rapidly donate its electrons and become the strongest base of the list

these can be ordered as follows

6 of origo MOST ACIDIC LEAST ACIDIC LEAST BASIC MOST BASIC