Question

Set(s) of reagents that convert(s) benzoyl chloride to aniline is/are

• A. (i) NH$_3$; (ii) Br$_2$, NaOH; (iii) H$_2$O
• B. (i) CH$_2$N$_2$; (ii) H$_2$O
• C. (i) NaN$_3$; (ii) H$_2$O
• D. (i) NH$_2$OH; (ii) TsCl, Pyridine; (iii) NaOH, $\Delta$; (iv) H$_2$O

Hint:

Hofmann, Curtius and Beckmann rearrangements are key reactions to convert carbonyl compounds into amines with one carbon less

Answer 1

The Correct Option is A, C, D

Step 1: Goal.
We must turn benzoyl chloride into aniline, which means losing one carbon by a rearrangement.

Step 2: Working routes.
Ammonia then bromine and base gives a Hofmann rearrangement. Sodium azide gives a Curtius rearrangement. The oxime route gives a Beckmann path. All three reach aniline.

Step 3: The failing route.
Diazomethane does not give aniline, so that option is wrong.

Step 4: Answer.
\[ \boxed{\text{A, C and D}} \]