Question

How will you distinguish between the following pair of compounds?

o-chlorotoluene and benzyl chloride

Answer 1

Property	o-Chlorotoluene	Benzyl chloride
Structure	Chlorine attached to a benzene ring at the ortho position with a methyl group on benzene.	Chlorine attached to a benzene ring at the ortho position with a methyl group on benzene.
Type of compound	Aromatic halide with chlorine directly on the benzene ring.	Benzylic alkyl halide (chlorine on side chain).
Reaction with aqueous NaOH.	No reaction or very slow reaction on heating.	Undergoes nucleophilic substitution, forming benzyl alcohol on heating.
Reaction with AgNO3 solution	No white precipitate is formed because no free Cl− ion is released.	White precipitate of AgCl is formed due to the release of Cl− ions.
Reactivity in nucleophilic substitution	Less reactive due to resonance stabilization of Cl on the aromatic ring.	Less reactive due to resonance stabilization of Cl on the aromatic ring.
Boiling point	The aromatic ring and the position of substitution contribute to its higher boiling point.	Lower boiling point compared to aromatic chlorides.
Combustion	Burns with a smoky flame due to its aromatic nature.	Burns with a clear flame.