Question

Given below are two statements:
Statement I: Aniline can be synthesized from using simpler reagents in the order 
i) Acidic KMnO4,
ii) Ammonia,
iii) Bromine and alkali
Statement II: Aniline can be converted into using reagents in the order
i) Bromine-H2O
ii) NaNO2/HCl (0 - 5 C)
(iii) H3PO2. 
In the light of the above statements, choose the correct answer from the options given below:

• A. Statement I is false but Statement II is true
• B. Both Statement I and Statement II are false
• C. Statement I is true but Statement II is false
• D. Both Statement I and Statement II are true

Hint:

Side chain oxidation of alkyl benzenes yields Benzoic acid. $H_3PO_2$ is a strong reducing agent for diazonium salts ($Ar-N_2^+ \to Ar-H$).

Answer 1

The Correct Option is D

Statement I: Propylbenzene is oxidized by acidic $KMnO_4$ to Benzoic Acid. Reaction with Ammonia and heat yields Benzamide. Hoffmann Bromamide degradation ($Br_2/NaOH$) converts Benzamide to Aniline. This is a valid sequence.
Statement II: Aniline reacts with Bromine water to form 2,4,6-tribromoaniline (white ppt). Diazotization ($NaNO_2/HCl$) converts $-NH_2$ to $-N_2^+ Cl^-$. Reduction with $H_3PO_2$ replaces the diazonium group with H, yielding 1,3,5-tribromobenzene. This is a valid sequence.
Both statements are correct.