Identify the incorrect statements. Choose the correct answer from the options given below:
- A and D Only
- A and C Only
- B and C Only
- A and B Only
Answer
(3) B and C Only
Solution
A. Correct – in benzylamine the lone pair on N is not in conjugation with the ring (an sp³ CH2 separates them), while in aniline it is delocalised into the ring. So benzylamine (pKb 4.70) is a stronger base than aniline (pKb 9.38).
B. Incorrect – as per NCERT, aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis, because aryl halides do not undergo nucleophilic substitution with the phthalimide anion.
C. Incorrect – Hofmann bromamide degradation removes one carbon: C6H5CH2CONH2 + Br2 + 4NaOH C6H5CH2NH2 + Na2CO3 + 2NaBr + 2H2O. Benzylamine has NH2 on an sp³ carbon, so it is an aliphatic (aralkyl) amine, not an aromatic amine.
D. Correct – p-nitroaniline → (diazotisation) p-nitrobenzenediazonium chloride → (warming with water) p-nitrophenol, which is acidic and dissolves in NaOH as sodium p-nitrophenoxide.
∴ Incorrect statements: B and C
Answer: (3)