CBSE Class 12 Chemistry 2024: question 32
Set in the CBSE Class 12 board exam of 2024, paper 56/1/1, section E, question 32, for 5 marks. Try it first; the hints and our step-by-step solution are below.
Q32 · 5 marks · Long answerAmines
Answer any five questions of the following :
- (a)1 mark
N,N-diethyl-benzenesulphonamide is insoluble in alkali. Give reason.
- (b)1 mark
Aniline does not undergo Friedel-Crafts reaction. Why ?
- (c)1 mark
Write a simple chemical test to distinguish between methylamine and aniline.
- (d)1 mark
Write the chemical reaction involved in Gabriel phthalimide synthesis.
- (e)1 mark
How will you convert aniline to p-bromoaniline ?
- (f)1 mark
Complete the following reaction : benzenediazonium chloride ()
- (g)1 mark
Write the structures of A and B in the following reaction : benzoic acid A B
Source: official question paper from cbse.gov.in (PDF). See it in the full 2024 board paper, set 56/1/1.
Hints
Open one hint at a time and try again before the next.
Hint 1
Sulphonamides dissolve in alkali only if an H is left on N; amines are Lewis bases.
Hint 2
For aniline reactions, think of protecting –NH₂ by acetylation and of diazonium/azo chemistry; heating an ammonium salt of an acid gives an amide.
Step-by-step solution
Each step shows the marks it earns, as an examiner would award them. Checked by an independent re-solve from the question paper.
- 1 mark
(a) In N,N-diethylbenzenesulphonamide, , there is no hydrogen on the nitrogen atom, so it is not acidic and does not form a salt with alkali; hence it is insoluble.
- 1 mark
(b) Aniline, a Lewis base, reacts with the catalyst AlCl₃ (Lewis acid) to form a salt; the nitrogen acquires a positive charge, which strongly deactivates the ring, so the Friedel–Crafts reaction does not occur.
- 1 mark
(c) Azo dye test: treat each with NaNO₂ + dil. HCl at 273–278 K and then with alkaline β-naphthol (or phenol). Aniline forms benzenediazonium chloride which couples to give an orange/red dye; methylamine gives methanol with evolution of N₂ and no dye.
- 1 mark
(d) Gabriel phthalimide synthesis: phthalimide potassium phthalimide N-alkylphthalimide + sodium phthalate. i.e. ;
- 1 mark
(e) Protect –NH₂ by acetylation, brominate, then hydrolyse:
- 1 mark
(f) (nitrobenzene).
(g) (A, benzamide) (B, aniline, by Hoffmann bromamide degradation).
Answer: (a) No H on N, not acidic; (b) forms salt with AlCl₃, ring deactivated; (c) azo dye test – aniline gives orange dye; (d) phthalimide → K-phthalimide → N-alkylphthalimide → RNH₂; (e) acetylation, bromination, hydrolysis; (f) nitrobenzene; (g) A = benzamide, B = aniline
Where the marks are
- No acidic H on nitrogen (1 mark)
- Salt formation with Lewis acid AlCl₃ (1 mark)
- Correct distinguishing test with observation (1 mark)
- Gabriel synthesis reaction (1 mark)
- Three-step conversion of aniline to p-bromoaniline (1 mark)
- Nitrobenzene as product (1 mark)
- A = benzamide, B = aniline (1 mark) — any five parts counted
Revise the chapter
- Chapter: Amines (notes, formulas, where marks are lost and every past question)
- Topic: Diazonium Salts and Their Reactions
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The question is transcribed from the official paper; figures are described in words. The solution, hints and chapter tag are ours. Spotted an error? Write tosupport@questionbuddy.in.