Problem 1
Write IUPAC names of the following compounds and classify them into primary. secondary and tertiary amines. (i) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHNH}_{2}\) (ii) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{NH}_{2}\) (iii) \(\mathrm{CH}_{3} \mathrm{NHCH}\left(\mathrm{CH}_{3}\right)_{2}\) (iv) \(\left(\mathrm{ClI}_{3}\right)_{3} \mathrm{CNIL}_{2}\) (v) \(\mathrm{C}_{6} \mathrm{II}_{5} \mathrm{NHCH}_{3}\) (vi) \(\left(\mathrm{CH}_{3} \mathrm{ClI}_{2}\right)_{2} \mathrm{NCH}_{3}\) (vii) \(\mathrm{m}-\mathrm{BrC}_{6} \mathrm{H}_{4} \mathrm{NH}_{2}\)
Problem 2
Give one chemical test to distinguish between the following pairs of compounds. (i) Methylamine and dimethylamine (ii) Secondary and tertiary amines (iii) Ethylamine and aniline (iv) Aniline and benzylamine (v) Aniline and N-methylaniline.
Problem 5
How will you convert: (i) Ethanoic acid into methanamine (ii) Hexanenitrile into 1 -aminopentane (iii) Methanol to ethanoic acid (iv) Ethanamine into methanamine (v) Ethanoic acid into propanoic acid (vi) Methanamine into ethanamine (vii) Nitromethane into dimethylamine (viii) Propanoic acid into ethanoic acid?
Problem 7
Write short notes on the following: (i) Carbylamine reaction (ii) Diazotisation (iii) Hofmann's bromamide reaction (iv) Coupling reaction (v) Ammonolysis (vi) Acetylation (vii) Gabriel phthalimide synthesis.
Problem 11
Complete the following reactions: (i) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{CHCl}_{3}+\) alc. \(\mathrm{KOH} \rightarrow\) (ii) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}_{2} \mathrm{Cl}+\mathrm{H}_{3} \mathrm{PO}_{2}+\mathrm{H}_{2} \mathrm{O} \rightarrow\) (iii) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{H}_{2} \mathrm{SO}_{4}(\) conc. \() \rightarrow\) (iv) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}_{2} \mathrm{Cl}+\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH} \rightarrow\) (v) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{Br}_{2}(\mathrm{aq}) \rightarrow\) (vi) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O} \rightarrow\)
Problem 12
Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?
Problem 13
Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid.
Problem 14
Give plausible explanation for each of the following: (i) Why are amines less acidic than alcohols of comparable molecular masses? (ii) Why do primary amines have higher boiling point than tertiary amines? (iii) Why are aliphatic amines stronger bases than aromatic amines?
