Q16-18P - Organic Chemistry (Mcmurry)

Question

What aromatic products would you obtain from the ${\mathbf{KMnO}}_4$ oxidation of the following substances?

a.

b.

Step-by-Step Solution

Answer

a. 

b.

Step 1: Oxidation of Aromatic Compounds

The benzene ring is inert to oxidizing agents like ${\mathrm{KMnO}}_4$ and ${\mathrm{Na}}_2{\mathrm{Cr}}_2{\mathrm{O}}_7$ . The alkyl side chains comprising benzylic hydrogen are oxidized to carboxyl groups by these reagents. Compounds that do not possess benzylic hydrogen atoms are not oxidized.

Step 2: Aromatic compounds obtained from the oxidation of different compounds

(a)The given compound 1-isopropyl-3-nitrobenzene reacts with ${\mathrm{KMnO}}_4$ and ${\mathrm{H}}_2\mathrm{O}$ to form 3-nitrobenzoic acid. The reaction can be given as:

Reaction(a)

(b)The given compound, 1-(tert-butyl)-4-methylbenzene reacts with ${\mathrm{KMnO}}_4$ and ${\mathrm{H}}_2\mathrm{O}$to form 4-(tert-butyl)benzoic acid. The reaction can be given as:

Reaction(b)