UNIT-IX AMINES

1. Why is an alkylamine more basic than ammonia?

Ans: Due to electron releasing inductive effect (+I) of alkyl group, the electron density on the
nitrogen atom increases and thus, it can donate the lone pair of electrons more easily than
ammonia.

2. Arrange the following compounds in an increasing order of basic strengths in their aqueous
solutions: NH3, CH3NH2, (CH3)2NH, (CH3)3N

Ans: Basicity order (due to stability of ammonium cation) (CH3)2 NH > CH3NH2 > (CH3)3
N > NH3

3. What are Amines derived from?

Ans: Amines are made from ammonia that is formed when hydrogen is replaced with aryl or
alkyl groups.

4. Give the IUPAC name of H2N — CH2—CH2—CH = CH2.

Ans: IUPAC name : But-3-ene-1-amine

5. Arrange the following compounds in an increasing order of their solubility in water:

C6H5NH2, (C2H5)2NH, C2H5NH2

Ans: C6H5NH2 < (C2H5)2NH < C2H5NH2

6. Give a chemical test to distinguish between ethylamine and aniline.

Ans: By Azo dye test: It involves the reaction of any aromatic primary amine with HNO2
(NaNO2 + dil. HCl) at 273-278 K followed by treatment with an alkaline solution of
naphthol when a brilliant yellow, orange or red coloured dye is obtained.

7. Arrange the following in the decreasing order of their basic strength in aqueous solutions:
CH3NH2, (CH3)2 NH, (CH3)3N and NH3

Ans: (CH3)2 NH > CH3NH2 > (CH3)3 N > NH3

8. Arrange the following in increasing order of their basic strength in aqueous solution:
CH3.NH2, (CH3)3N, (CH3)2NH

Ans:

9. Write the structure of 2-aminotoluene.

Ans:

10. Write the structure of N-methylethanamine.

Ans.: Structure of n-methylethanamine : H3C—H2C—NH—CH2

11. Write the structure of prop-2-en-l-amine. Ans: H2C=CH—H2C—NH2

12. How may methyl bromide be preferentially converted to methyl isocyanide?

Ans

13. Arrange the following compounds in increasing order of solubility in water : C6H5NH2,
(C2H5)2NH, C2H5NH2

Ans: C6H5NH2 < (C2H5)2NH < C2H5NH2,

14. Arrange the following in increasing order of basic strength : C6H5NH2, C6H5NHCH3,
C6H5CH2NH2

Ans: C6H5NH2 < C6H5NHCH3 < C6H5CH2NH2

15. Arrange the following in increasing order of basic strength : C6H5NH2, C6H5NHCH3,
C6H5N(CH3)2

Ans: C6H5N(CH3)2 > C6H5NHCH3 > C6H5NH2

16. The conversion of primary aromatic amines into diazonium salts is known as

Ans: Diazotization.

17. N-ethylethanamine boils at 329.3K and butanamine boils at 350.8K, although both are
isomeric in nature Give reason.

Ans: Due to the presence of two hydrogen atoms, the intermolecular association is more in
primary amines than in secondary amines.

18. Out of CH3—NH2 and (CH3)3N, which one has higher boiling point?

Ans: CH3—NH2 has higher boiling point than (CH3)3N.

19. Write chemical equations for the Reaction of ethanolic NH3 with C2H5Cl.

Ans:

20. Arrange the following in increasing order of basic strength Aniline, p-Nitroaniline and p-
Toluidine

Ans:

21. Write the IUPAC name of the given compound:

Ans: 2, 4, 6-Tribromoaniline

22. Write IUPAC name of the following compound: (CH3CH2)2NCH3

Ans: N-Ethyl-N-methylethanamine

23. Write the IUPAC name of the following compound:

CH3NHCH(CH3)2

Ans: IUPAC name: N-Methylpropan-2-amine

24. Write the IUPAC name of the following compound: (CH3)2N-CH2CH3

Ans: IUPAC name: N, N Dimethylamine

25. Aniline cannot be prepared by the ammonolysis of chlorobenzene under normal

conditions. Give reason.

Ans: In case of chlorobenzene, the C—Cl bond is quite difficult to break as it acquires a
partial double bond character due to conjugation.

26. Write the structure of p-toluidene.

Ans:

27. Name two alkaloids present in neurotransmitters.

Ans: Dopamine , Epinephrine

28. Write the structure of N-methyl ethanamine.

Ans: H3C—H2C—NH—CH3

29. Which diazonium salt is insoluble in water?

Ans: C6H5N2+BF4 – (Benzene diazonium fluoro borate) Benzene diazonium flouroborate is

slable at room temperature and is insoluble in water due to its high lattice enthalpy.

30. Why are aliphatic diazonium salts unstable?

Ans: Since there is no resonance in aliphatic diazonium salts, so these are highly unstable and
readily convert to corresponding alcohols.

31. Aniline does not undergoes Friedel-Crafts reaction. Why?

Ans: due to salt formation with aluminium chloride, the Lewis acid, which is used as a
catalyst

32. Aniline is less basic than cyclohexylamine.Give reason.

Ans: Due to +I effect of cyclohexyl group electron density increases on N-atom of -NH2
group, which increases basic strength of cyclohexylamine

33. Aromatic amines cannot be synthesized by Gabriel phthalimide synthesis.why?

Ans: Because aryl halides do not undergo nucleophilic substitution with the phthalimide-
formed anion, which restricts further reaction.

34. Write IUPAC name of the following compound :

Ans: IUPAC name : N, N-Dimethylbutanamine.

35. Give the chemical tests to distinguish between Ethyl amine and Aniline.

Ans: By Azo dye test: It involves the reaction of any aromatic primary amine with
HNO2(NaNO2 + dil. HCl) at 273-278 K followed by treatment with an alkaline solution of
2-naphthol when a brilliant yellow, orange or red coloured dye is obtained.

36. What is the role of HNO3 in the nitrating mixture used for the nitration of benzene?

Ans: HNO3 acts as a base in the nitrating mixture and provides the electrophile NO2+ ion for
the nitration of benzene.

37. Why is the NH2 group of aniline acetylated before carrying out nitration?

Ans: NH2 group of aniline is acetylated first so that controlled nitration can occur at the para
position. If the NH2 group of aniline is not acetylated, then a mixture of ortho, meta and para
products will form.

38. What is the best reagent to convert nitrile to primary amine?

Ans: LiAlH4 and Sodium/Alcohol are the best reagents

39. What is Hinsberg reagent?

Ans: Hinsberg reagent is an alternative name for benzene sulfonyl chloride (C6H5SO2Cl). It
is used to detect and distinguish primary, secondary, and tertiary amines in a given sample.

40. Under what reaction conditions (acidic/basic) the coupling reaction of aryl diazonium
chloride with aniline is carried out?

Ans: Coupling reaction of aryl diazonium chloride with aniline is carried out in mildly acidic
conditions, i.e. pH=4−5.

41. Arrange the following compounds in increasing order of dipole moment. CH3CH2CH3,
CH3CH2NH2, CH3CH2OH. Ans: CH3CH2CH3 < CH3CH2NH2 < CH3CH2OH

42. How can you distinguish between Methylamine and Dimethylamine

Ans: By Carbylamine test: Methylamine being a primary amine gives this test but
Dimethylamine being a secondary amine does not.

43. How can you distinguish between Aniline and N-methylaniline

Ans: By Carbylamine test : Aniline is a 1° aromatic amine while N-methylaniline is a

secondary aromatic amine. Therefore only 1° aromatic amine gives this test.
44. Describe Carbylamine reaction giving the relevant chemical equation.

Ans: Carbylamine reaction : Aliphatic and aromatic primary amines on heating with
chloroform and ethanolic KOH form isocyanides or carbylamines which are foul smelling
substances. This reaction is known as carbylamines reaction.

45. Describe Hofmann’s bromamide reaction with relevant chemical equation

Ans: Hofmann’s bromamide reaction : Primary amines can be prepared by treating an amide
with Br2 in an aqueous or alcoholic soln of NaOH.

46. Complete the reaction : C6H5N2Cl + H3PO2 + H2O →

Ans: C6H5N2Cl + H3PO2 + H2O →C6H6 + N2 + H3PO3 + HCl

47. Give IUPAC names of the following compounds :

Ans: (a) IUPAC name : Methyl prop-2-en-1-amine (b) IUPAC name : Phenyl acetamide

48. Electrophilic susbstitution in case of aromatic amines takes place more readily than
benzene.

Ans: Aniline exists as a resonance hybrid of five structures. The electron density is maximum
at ortho and para positions to the – NH2 group.

49. Illustrate Sandmeyer’s reaction

Ans:

50. Ethanamide is a weaker base than ethanamine.Give reason.

Ans: In ethanamide the lone pair of electron of N-atom is not available due to resonance
structure.

51. Explain why MeNH2 is a stronger base than MeOH?

Ans: Nitrogen is less electronegative than oxygen; therefore lone pairs of electrons on
nitrogen are readily available for donation. Hence, MeNH2 is more basic than MeOH.

52. What is the role of pyridine in the acylation reaction of amines?

Ans: Pyridine acts as an acceptor for the acid by-product formed in the reaction. Thus, it
removes the side product, i.e. HCl, from the reaction mixture

53. Under what reaction conditions (acidic/basic) the coupling reaction of aryl diazonium
chloride with aniline is carried out.

Ans: Coupling reaction of aryl diazonium chloride with aniline is carried out in mildly acidic
conditions, i.e. pH=4−5.