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Amines Exercises Solutions
- Q9.1 (i): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (i) \((CH_{3})_{2}CHNH_{2}\)
- Q9.1 (ii): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (ii) \(CH_{3}(CH_{2})_{2}NH_{2}\)
- Q9.1 (iii): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (iii) \(CH_{3}NHCH(CH_{3})_{2}\)
- Q9.1 (iv): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (iv) \((CH_{3})_{3}CNH_{2}\)
- Q9.1 (v): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (v) \(C_{6}H_{5}NHCH_{3}\)
- Q9.1 (vi): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (vi) \((CH_{3}CH_{2})_{2}NCH_{3}\)
- Q9.1 (vii): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (vii) \(m–BrC_{6}H_{4}NH_{2}\)
- Q9.1(i): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (i) (( (CH_{3})_{2}CHNH_{2} ))
- Q9.1(ii): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (ii) (( CH_{3}(CH_{2})_{2}NH_{2} ))
- Q9.1(iii): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (iii) (( CH_{3}NHCH(CH_{3})_{2} ))
- Q9.1(iv): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (iv) (( (CH_{3})_{3}CNH_{2} ))
- Q9.1(v): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (v) (( C_{6}H_{5}NHCH_{3} ))
- Q9.1(vi): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (vi) (( (CH_{3}CH_{2})_{2}NCH_{3} ))
- Q9.1(vii): Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. (vii) (( m–BrC_{6}H_{4}NH_{2} ))
- Q9.10: An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms compound ‘B’ which on heating with \(Br_{2}\) and \(KOH\) forms a compound ‘C’ of molecular formula \(C_{6}H_{7}N\). Write the structures and IUPAC names of compounds A, B and C.
- Q9.10: An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms compound ‘B’ which on heating with (( Br_{2} )) and KOH forms a compound ‘C’ of molecular formula (( C_{6}H_{7}N )). Write the structures and IUPAC names of compounds A, B and C.
- Q9.11: Complete the following reactions:
- Q9.11 (i): Complete the following reactions: (i) \(C_{6}H_{5}NH_{2} + CHCl_{3} + \text{alc.}KOH \rightarrow\)
- Q9.11 (ii): Complete the following reactions: (ii) \(C_{6}H_{5}N_{2}^{+}Cl^{-} + H_{3}PO_{2} + H_{2}O \rightarrow\)
- Q9.11 (iii): Complete the following reactions: (iii) \(C_{6}H_{5}NH_{2} + H_{2}SO_{4} (\text{conc.}) \rightarrow\)
- Q9.11 (iv): Complete the following reactions: (iv) \(C_{6}H_{5}N_{2}^{+}Cl^{-} + C_{2}H_{5}OH \rightarrow\)
- Q9.11 (v): Complete the following reactions: (v) \(C_{6}H_{5}NH_{2} + Br_{2} (aq) \rightarrow\)
- Q9.11 (vi): Complete the following reactions: (vi) \(C_{6}H_{5}NH_{2} + (CH_{3}CO)_{2}O \rightarrow\)
- Q9.11(i): Complete the following reactions: (i) (( C_{6}H_{5}NH_{2} + CHCl_{3} + \text{alc.KOH} \rightarrow ))
- Q9.11(ii): Complete the following reactions: (ii) (( C_{6}H_{5}N_{2}^{+}Cl^{-} + H_{3}PO_{2} + H_{2}O \rightarrow ))
- Q9.11(iii): Complete the following reactions: (iii) (( C_{6}H_{5}NH_{2} + H_{2}SO_{4}(\text{conc.}) \rightarrow ))
- Q9.11(iv): Complete the following reactions: (iv) (( C_{6}H_{5}N_{2}^{+}Cl^{-} + C_{2}H_{5}OH \rightarrow ))
- Q9.11(v): Complete the following reactions: (v) (( C_{6}H_{5}NH_{2} + Br_{2}(aq) \rightarrow ))
- Q9.11(vi): Complete the following reactions: (vi) (( C_{6}H_{5}NH_{2} + (CH_{3}CO)_{2}O \rightarrow ))
- Q9.11(vii): Complete the following reactions: (vii) (( C_{6}H_{5}N_{2}^{+}Cl^{-} \xrightarrow{(i)HBF_{4} (ii)NaNO_{2}/Cu, \Delta} ))
- Q9.12: Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?
- Q9.12: Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?
- Q9.13 (i): Write the reactions of (i) aromatic primary amines with nitrous acid.
- Q9.13 (ii): Write the reactions of (ii) aliphatic primary amines with nitrous acid.
- Q9.13(i): Write the reactions of aromatic primary amines with nitrous acid.
- Q9.13(ii): Write the reactions of aliphatic primary amines with nitrous acid.
- Q9.14 (i): Give plausible explanation for each of the following: (i) Why are amines less acidic than alcohols of comparable molecular masses?
- Q9.14 (ii): Give plausible explanation for each of the following: (ii) Why do primary amines have higher boiling point than tertiary amines?
- Q9.14 (iii): Give plausible explanation for each of the following: (iii) Why are aliphatic amines stronger bases than aromatic amines?
- Q9.14(i): Give plausible explanation for each of the following: (i) Why are amines less acidic than alcohols of comparable molecular masses?
- Q9.14(ii): Give plausible explanation for each of the following: (ii) Why do primary amines have higher boiling point than tertiary amines?
- Q9.14(iii): Give plausible explanation for each of the following: (iii) Why are aliphatic amines stronger bases than aromatic amines?
- Q9.2 (i): Give one chemical test to distinguish between the following pairs of compounds. (i) Methylamine and dimethylamine
- Q9.2 (ii): Give one chemical test to distinguish between the following pairs of compounds. (ii) Secondary and tertiary amines
- Q9.2 (iii): Give one chemical test to distinguish between the following pairs of compounds. (iii) Ethylamine and aniline
- Q9.2 (iv): Give one chemical test to distinguish between the following pairs of compounds. (iv) Aniline and benzylamine
- Q9.2 (v): Give one chemical test to distinguish between the following pairs of compounds. (v) Aniline and N-methylaniline.
- Q9.2(i): Give one chemical test to distinguish between the following pairs of compounds. (i) Methylamine and dimethylamine
- Q9.2(ii): Give one chemical test to distinguish between the following pairs of compounds. (ii) Secondary and tertiary amines
- Q9.2(iii): Give one chemical test to distinguish between the following pairs of compounds. (iii) Ethylamine and aniline
- Q9.2(iv): Give one chemical test to distinguish between the following pairs of compounds. (iv) Aniline and benzylamine
- Q9.2(v): Give one chemical test to distinguish between the following pairs of compounds. (v) Aniline and N-methylaniline.
- Q9.3 (i): Account for the following: (i) \(pK_{b}\) of aniline is more than that of methylamine.
- Q9.3 (ii): Account for the following: (ii) Ethylamine is soluble in water whereas aniline is not.
- Q9.3 (iii): Account for the following: (iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
- Q9.3 (iv): Account for the following: (iv) Although amino group is \(o–\) and \(p–\) directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of \(m\)-nitroaniline.
- Q9.3 (v): Account for the following: (v) Aniline does not undergo Friedel-Crafts reaction.
- Q9.3 (vi): Account for the following: (vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines.
- Q9.3 (vii): Account for the following: (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.
- Q9.3(i): Account for the following: (i) (( pK_{b} )) of aniline is more than that of methylamine.
- Q9.3(ii): Account for the following: (ii) Ethylamine is soluble in water whereas aniline is not.
- Q9.3(iii): Account for the following: (iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
- Q9.3(iv): Account for the following: (iv) Although amino group is (( o– )) and (( p– )) directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of (( m ))-nitroaniline.
- Q9.3(v): Account for the following: (v) Aniline does not undergo Friedel-Crafts reaction.
- Q9.3(vi): Account for the following: (vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines.
- Q9.3(vii): Account for the following: (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.
- Q9.4 (i): Arrange the following: (i) In decreasing order of the \(pK_{b}\) values: \(C_{2}H_{5}NH_{2}\), \(C_{6}H_{5}NHCH_{3}\), \((C_{2}H_{5})_{2}NH\) and \(C_{6}H_{5}NH_{2}\)
- Q9.4 (ii): Arrange the following: (ii) In increasing order of basic strength: \(C_{6}H_{5}NH_{2}\), \(C_{6}H_{5}N(CH_{3})_{2}\), \((C_{2}H_{5})_{2}NH\) and \(CH_{3}NH_{2}\)
- Q9.4 (iii)(a): Arrange the following: (iii) In increasing order of basic strength: (a) Aniline, \(p\)-nitroaniline and \(p\)-toluidine
- Q9.4 (iii)(b): Arrange the following: (iii) In increasing order of basic strength: (b) \(C_{6}H_{5}NH_{2}\), \(C_{6}H_{5}NHCH_{3}\), \(C_{6}H_{5}CH_{2}NH_{2}\).
- Q9.4 (iv): Arrange the following: (iv) In decreasing order of basic strength in gas phase: \(C_{2}H_{5}NH_{2}\), \((C_{2}H_{5})_{2}NH\), \((C_{2}H_{5})_{3}N\) and \(NH_{3}\)
- Q9.4 (v): Arrange the following: (v) In increasing order of boiling point: \(C_{2}H_{5}OH\), \((CH_{3})_{2}NH\), \(C_{2}H_{5}NH_{2}\)
- Q9.4 (vi): Arrange the following: (vi) In increasing order of solubility in water: \(C_{6}H_{5}NH_{2}\), \((C_{2}H_{5})_{2}NH\), \(C_{2}H_{5}NH_{2}\).
- Q9.4(i): Arrange the following: (i) In decreasing order of the (( pK_{b} )) values: (( C_{2}H_{5}NH_{2} )), (( C_{6}H_{5}NHCH_{3} )), (( (C_{2}H_{5})_{2}NH )) and (( C_{6}H_{5}NH_{2} ))
- Q9.4(ii): Arrange the following: (ii) In increasing order of basic strength: (( C_{6}H_{5}NH_{2} )), (( C_{6}H_{5}N(CH_{3})_{2} )), (( (C_{2}H_{5})_{2}NH )) and (( CH_{3}NH_{2} ))
- Q9.4(iii)(a): Arrange the following: (iii) In increasing order of basic strength: (a) Aniline, (( p ))-nitroaniline and (( p ))-toluidine
- Q9.4(iii)(b): Arrange the following: (iii) In increasing order of basic strength: (b) (( C_{6}H_{5}NH_{2} )), (( C_{6}H_{5}NHCH_{3} )), (( C_{6}H_{5}CH_{2}NH_{2} )).
- Q9.4(iv): Arrange the following: (iv) In decreasing order of basic strength in gas phase: (( C_{2}H_{5}NH_{2} )), (( (C_{2}H_{5})_{2}NH )), (( (C_{2}H_{5})_{3}N )) and (( NH_{3} ))
- Q9.4(v): Arrange the following: (v) In increasing order of boiling point: (( C_{2}H_{5}OH )), (( (CH_{3})_{2}NH )), (( C_{2}H_{5}NH_{2} ))
- Q9.4(vi): Arrange the following: (vi) In increasing order of solubility in water: (( C_{6}H_{5}NH_{2} )), (( (C_{2}H_{5})_{2}NH )), (( C_{2}H_{5}NH_{2} )).
- Q9.5 (i): How will you convert: (i) Ethanoic acid into methanamine
- Q9.5 (ii): How will you convert: (ii) Hexanenitrile into 1-aminopentane
- Q9.5 (iii): How will you convert: (iii) Methanol to ethanoic acid
- Q9.5 (iv): How will you convert: (iv) Ethanamine into methanamine
- Q9.5 (v): How will you convert: (v) Ethanoic acid into propanoic acid
- Q9.5 (vi): How will you convert: (vi) Methanamine into ethanamine
- Q9.5 (vii): How will you convert: (vii) Nitromethane into dimethylamine
- Q9.5 (viii): How will you convert: (viii) Propanoic acid into ethanoic acid?
- Q9.5(i): How will you convert: (i) Ethanoic acid into methanamine
- Q9.5(ii): How will you convert: (ii) Hexanenitrile into 1-aminopentane
- Q9.5(iii): How will you convert: (iii) Methanol to ethanoic acid
- Q9.5(iv): How will you convert: (iv) Ethanamine into methanamine
- Q9.5(v): How will you convert: (v) Ethanoic acid into propanoic acid
- Q9.5(vi): How will you convert: (vi) Methanamine into ethanamine
- Q9.5(vii): How will you convert: (vii) Nitromethane into dimethylamine
- Q9.5(viii): How will you convert: (viii) Propanoic acid into ethanoic acid?
- Q9.6: Describe a method for the identification of primary, secondary and tertiary amines. Also write chemical equations of the reactions involved.
- Q9.6: Describe a method for the identification of primary, secondary and tertiary amines. Also write chemical equations of the reactions involved.
- Q9.7 (i): Write short notes on the following: (i) Carbylamine reaction
- Q9.7 (ii): Write short notes on the following: (ii) Diazotisation
- Q9.7 (iii): Write short notes on the following: (iii) Hofmann’s bromamide reaction
- Q9.7 (iv): Write short notes on the following: (iv) Coupling reaction
- Q9.7 (v): Write short notes on the following: (v) Ammonolysis
- Q9.7 (vi): Write short notes on the following: (vi) Acetylation
- Q9.7 (vii): Write short notes on the following: (vii) Gabriel phthalimide synthesis.
- Q9.7(i): Write short notes on the following: (i) Carbylamine reaction
- Q9.7(ii): Write short notes on the following: (ii) Diazotisation
- Q9.7(iii): Write short notes on the following: (iii) Hofmann’s bromamide reaction
- Q9.7(iv): Write short notes on the following: (iv) Coupling reaction
- Q9.7(v): Write short notes on the following: (v) Ammonolysis
- Q9.7(vi): Write short notes on the following: (vi) Acetylation
- Q9.7(vii): Write short notes on the following: (vii) Gabriel phthalimide synthesis.
- Q9.8 (i): Accomplish the following conversions: (i) Nitrobenzene to benzoic acid
- Q9.8 (ii): Accomplish the following conversions: (ii) Benzene to \(m\)-bromophenol
- Q9.8 (iii): Accomplish the following conversions: (iii) Benzoic acid to aniline
- Q9.8 (iv): Accomplish the following conversions: (iv) Aniline to 2,4,6-tribromofluorobenzene
- Q9.8 (ix): Accomplish the following conversions: (ix) Aniline to benzyl alcohol.
- Q9.8 (v): Accomplish the following conversions: (v) Benzyl chloride to 2-phenylethanamine
- Q9.8 (vi): Accomplish the following conversions: (vi) Chlorobenzene to \(p\)-chloroaniline
- Q9.8 (vii): Accomplish the following conversions: (vii) Aniline to \(p\)-bromoaniline
- Q9.8 (viii): Accomplish the following conversions: (viii) Benzamide to toluene
- Q9.8(i): Accomplish the following conversions: (i) Nitrobenzene to benzoic acid
- Q9.8(ii): Accomplish the following conversions: (ii) Benzene to m-bromophenol
- Q9.8(iii): Accomplish the following conversions: (iii) Benzoic acid to aniline
- Q9.8(iv): Accomplish the following conversions: (iv) Aniline to 2,4,6-tribromofluorobenzene
- Q9.8(ix): Accomplish the following conversions: (ix) Aniline to benzyl alcohol.
- Q9.8(v): Accomplish the following conversions: (v) Benzyl chloride to 2-phenylethanamine
- Q9.8(vi): Accomplish the following conversions: (vi) Chlorobenzene to p-chloroaniline
- Q9.8(vii): Accomplish the following conversions: (vii) Aniline to p-bromoaniline
- Q9.8(viii): Accomplish the following conversions: (viii) Benzamide to toluene
- Q9.9: Give the structures of A, B and C in the following reactions:
- Q9.9: Give the structures of A, B and C in the following reactions:
- Q9.9: Give the structures of A, B and C in the following reactions:
- Q9.9: Give the structures of A, B and C in the following reactions:
- Q9.9: Give the structures of A, B and C in the following reactions:
- Q9.9: Give the structures of A, B and C in the following reactions:
- Q9.9(i): Give the structures of A, B and C in the following reactions: (i) (( CH_{3}CH_{2}I \xrightarrow{NaCN} A \xrightarrow{OH^{-}/ \text{Partial hydrolysis}} B \xrightarrow{NaOH + Br_{2}} C ))
- Q9.9(ii): Give the structures of A, B and C in the following reactions: (ii) (( C_{6}H_{5}N_{2}^{+}Cl^{-} \xrightarrow{CuCN} A \xrightarrow{H_{2}O/H^{+}} B \xrightarrow{NH_{3}, \Delta} C ))
- Q9.9(iii): Give the structures of A, B and C in the following reactions: (iii) (( CH_{3}CH_{2}Br \xrightarrow{KCN} A \xrightarrow{LiAlH_{4}} B \xrightarrow{HNO_{2}, 0^{\circ}C} C ))
- Q9.9(iv): Give the structures of A, B and C in the following reactions: (iv) (( C_{6}H_{5}NO_{2} \xrightarrow{Fe/HCl} A \xrightarrow{NaNO_{2} + HCl, 273 K} B \xrightarrow{H_{2}O/H^{+}, \Delta} C ))
- Q9.9(v): Give the structures of A, B and C in the following reactions: (v) (( CH_{3}COOH \xrightarrow{NH_{3}, \Delta} A \xrightarrow{NaOBr} B \xrightarrow{NaNO_{2}/HCl} C ))
- Q9.9(vi): Give the structures of A, B and C in the following reactions: (vi) (( C_{6}H_{5}NO_{2} \xrightarrow{Fe/HCl} A \xrightarrow{HNO_{2}, 273K} B \xrightarrow{C_{6}H_{5}OH} C ))
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