Amines

(i) Write structures of different isomeric amines corresponding to the molecular formula, C₄H₁₁N. (ii) Write IUPAC names of all the isomers. (iii) What type of isomerism is exhibited by different pairs of amines?

Arrange the following in increasing order of their basic strength: (i) C₂H₅NH₂, C₆H₅NH₂, NH₃, C₆H₅CH₂NH₂ and (C₂H₅)₂NH (ii) C₂H₅NH₂, (C₂H₅)₂NH, (C₂H₅)₃N, C₆H₅NH₂ (iii) CH₃NH₂, (CH₃)₂NH, (CH₃)₃N, C₆H₅NH₂, C₆H₅CH₂NH₂.

Complete the following acid-base reactions and name the products: (i) CH₃CH₂CH₂NH₂ + HCl → (ii) (C₂H₅)₃N + HCl →

Write reactions of the final alkylation product of aniline with excess of methyl iodide in the presence of sodium carbonate solution.

Write chemical reaction of aniline with benzoyl chloride and write the name of the product obtained.

Write structures of different isomers corresponding to the molecular formula, C₃H₉N. Write IUPAC names of the isomers which will liberate nitrogen gas on treatment with nitrous acid.

Convert (i) 3-Methylaniline into 3-nitrotoluene. (ii) Aniline into 1,3,5 - tribromobenzene.

Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (i) (CH₃)₂CHNH₂ (ii) CH₃(CH₂)₂NH₂ (iii) CH₃NHCH(CH₃)₂ (iv) (CH₃)₃CNH₂ (v) C₆H₅NHCH₃ (vi) (CH₃CH₂)₂NCH₃ (vii) m-BrC₆H₄NH₂

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.

Account for the following: (i) pKb of aniline is more than that of methylamine. (ii) Ethylamine is soluble in water whereas aniline is not. (iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide. (iv) Although amino group is o- and p- directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline. (v) Aniline does not undergo Friedel-Crafts reaction. (vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines. (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.

Arrange the following: (i) In decreasing order of the pKb values: C₂H₅NH₂, C₆H₅NHCH₃, (C₂H₅)₂NH and C₆H₅NH₂ (ii) In increasing order of basic strength: C₆H₅NH₂, C₆H₅N(CH₃)₂, (C₂H₅)₂NH and CH₃NH₂ (iii) In increasing order of basic strength: (a) Aniline, p-nitroaniline and p-toluidine (b) C₆H₅NH₂, C₆H₅NHCH₃, C₆H₅CH₂NH₂. (iv) In decreasing order of basic strength in gas phase: C₂H₅NH₂, (C₂H₅)₂NH, (C₂H₅)₃N and NH₃ (v) In increasing order of boiling point: C₂H₅OH, (CH₃)₂NH, C₂H₅NH₂ (vi) In increasing order of solubility in water: C₆H₅NH₂, (C₂H₅)₂NH, C₂H₅NH₂.

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?

Describe a method for the identification of primary, secondary and tertiary amines. Also write chemical equations of the reactions involved.

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.

Accomplish the following conversions: (i) Nitrobenzene to benzoic acid (ii) Benzene to m-bromophenol (iii) Benzoic acid to aniline (iv) Aniline to 2,4,6-tribromofluorobenzene (v) Benzyl chloride to 2-phenylethanamine (vi) Chlorobenzene to p-chloroaniline (vii) Aniline to p-bromoaniline (viii) Benzamide to toluene (ix) Aniline to benzyl alcohol.

Give the structures of A, B and C in the following reactions: (i) CH₃CH₂I →[NaCN] A →[OH⁻] B →[NaOH+Br₂] C (ii) C₆H₅N₂Cl →[CuCN] A →[H₂O/H⁺] B →[NH₃/Δ] C (iii) CH₃CH₂Br →[KCN] A →[LiAlH₄] B →[HNO₂/0°C] C (iv) C₆H₅NO₂ →[Fe/HCl] A →[NaNO₂+HCl] B →[H₂O/H⁺] C (v) CH₃COOH →[NH₃/Δ] A →[NaOBr] B →[NaNO₂/HCl] C (vi) C₆H₅NO₂ →[Fe/HCl] A →[HNO₂/273K] B →[C₆H₅OH] C

An aromatic compound 'A' on treatment with aqueous ammonia and heating forms compound 'B' which on heating with Br₂ and KOH forms a compound 'C' of molecular formula C₆H₇N. Write the structures and IUPAC names of compounds A, B and C.

Complete the following reactions: (i) C₆H₅NH₂ + CHCl₃ + alc.KOH → (ii) C₆H₅N₂Cl + H₃PO₂ + H₂O → (iii) C₆H₅NH₂ + H₂SO₄ (conc.) → (iv) C₆H₅N₂Cl + C₂H₅OH → (v) C₆H₅NH₂ + Br₂ (aq) → (vi) C₆H₅NH₂ + (CH₃CO)₂ O → (vii) C₆H₅N₂Cl →[(i)HBF₄] [(ii) NaNO₂/Cu, Δ]

Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?

Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid.