CLASS XII CHEMISTRY ASSIGNMENT UNIT : AMINES

1. Arrange the following in decreasing order of solubility in water:

a)(CH3)3N, (CH3)2H, CH3NH2 
b)C6H5NH2, (C2H5)2NH, C2H5NH2 
2. Why do amines act as nucleophiles? Give example of a reaction in which methylamine acts as a
nucleophile.
3. Three isomeric amines A, B and C have the molecular formula C3H9N. Compound A on reaction
with benzene sulphonyl chloride forms a product which is soluble in NaOH . Compound B on reaction
with benzene sulphonyl chloride forms a product which is insoluble in NaOH  and compound C does
not react with benzene sulphonyl chloride. Identify A, B and C.
4. Write the structure of i)n-methylhexanamine. Ii)2-amino toluene.
5.Write the IUPAC name of the given compound:

6.Arrange the following in increasing order of their basic strength in an aqueous solution:
i) CH3NH2, (CH3)3N, (CH3)2NH
ii)C6H5NH2, C6H5N(CH3)2, (C6H5)2NH, and CH3NH2 
7.Write the IUPAC name of the compound .

8.Arrange the following in increasing order of base strength in the gas phase:
(C2H5)3N, C2H5NH2, (C2H5)2NH
9.Arrange the following in increasing order of boiling points:
(CH3)3N, C2H5OH, C2H5NH2 
10.Arrange the following in the increasing order of their pKb values.
C6H5NH2, C2H5NH2, C6H5NHCH3 
11.Write IUPAC name of the following compound: CH 3NHCH(CH3)2 , (CH3CH2)2NCH3 

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

13.Give the structures of A, B, and C in the following reactions:

14.Complete the following reaction equations:

(i) C6H5N2CI + H3PO2 + H20 →
(ii) C6H5NH2 + Br2(aq) →
15.Give the structures of products A, B, and C in the following reactions:
16.Write the structures of A, B, and C In the following:)

17.Give a chemical test to distinguish between (i) Aniline and benzylamine (ii)ethylamine and aniline.
(iii) Aniline and N-methylaniline.
18. 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 C 6H7N. Write the
structures and IUPAC names of compounds A, B, and C.
19.Account for the following:
(a) Gabriel phthalimide synthesis is not preferred for preparing aromatic primary amines.
(b) On reaction with benzene sulphonyl chloride, primary amine yields product soluble in alkali
whereas secondary amine yields product insoluble in alkali. Answer:
20.Write equations of the following reactions:
(i) Acetylation of Aniline
(ii) Coupling reaction:
(iii) Carbylamine reaction:
21.An aromatic compound ‘A’ on heating with Br 2 and KOH forms a compound ‘B’ of molecular
formula C6H7N which on reacting with CHCl3 and alcoholic KOH produces a foul-smelling compound
‘C’. Write the structures and IUPAC names of compounds A, B, and C.

22.(a) Write the product formed when

(i) 2-chioropropane is treated with aic. KOH.
(ii) Aniline reacts with conc. H2SO4 at 453 – 473 K.
(b) When aniline is heated with CHCl3 and aic. KOH, a foul-smelling compound is formed. What is this
compound?
23.a) Identify ‘A’ and ‘B’ In the following reaction:

(b) Why does aniline not undergo Friedel-Crafts reaction?

24.Complete the following reactions: (i) CH3CH2NH2 + CHCl3 + ale. KOH → (ii) C6H5N2+Cl– →
25.Write the main products of the following reactions:

26.Account for the following:

(i) Primary amines (R-NH2) have a higher boiling point than tertiary amines (R 3N).
(ii) Aniline does not undergo Friedel — Crafts reaction.
(iii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
27.Give the structures of A, B, and C in the following reactions:

28.Give the structures of A, B, and C in the following reactions:

29.How will you convert the following:

(i) Nitrobenzene into aniline
(ii) Ethanoic acid into methanamine
(iii) Aniline into N-phenylethylamine
(Write the chemical equations involved.)
30.Write chemical equations for the following conversions:
(i) Nitrobenzene to benzoic acid.
(ii) Benzyl chloride to 2-phenytethanamine.
(iii) Aniline to benzyl alcohol.
31.Why is ethylamine soluble in water whereas aniline is not?
32. (i) Illustrate the following reactions giving a suitable example in each case:
(a) Hoffmann bromamide degradation reaction
(b) Diazotisation
(c) Gabriel phthalimide synthesis
(ii) Distinguish between the following pairs of compounds:
(a) Aniline and N-methylaniline
(b) (CH3)2NH and (CH3)3N
32.Complete the following reactions:
33.An organic compound A’ with molecular formula C 7H7NO reacts with Br2/aq KOH to give
compound B’, which upon reaction with NaNO 2 and HCI at OC gives C’. Compound C’ on heating with
CH3CH2OH gives a hydrocarbon D’. Compound B’ on further reaction with Br 2 water gives a white
precipitate of compound E’. Identify the compounds A, B, C, D, and E; also justify your answer by
giving relevant chemical equations.:

34. Carry out the following conversions

i)Ethanoic acid to ethanamine  ii)p-toluidine to 2-bromo-4-methylaniline  iii)Benzene to sulphanilic
acid
35.Explain why
(i) The C−N− bond angle in trimethyl amine is 108∘108∘ 
ii) The quaternary ammonium salts having four different alkyl groups are optically active.
(iii) Alkylamines are more basic than ammonia.
(iv) Aniline cannot be prepared by Gabriel phthalimide synthesis.
(v) Garbriel phthalimide synthesis is preferably used for synthesising primary amines.
(vi) Ethylamine is soluble in water but aniline is not.
(vii) Amines are soluble in dilute Acids.
(viii) Amines have lower boiling point than alcohols of comparable molecular masses.
(ix) 1° amines have higher boiling points than 2° amines which in turn, are higher boiling than 3°
amines.
(x)The pK value of benzeneamine is 9.33 while that of ammonia is 4.75.
(xi) Aniline does not undergo Friedel-Crafts reaction.
(xiv)Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide. 
(xv)Diazonium salt of aromatic amines are more stable than the diazonium salts of aliphatic amines.
(xvi)Although amino group is o, p-directing in aromatic electrophilic substitution reactions, aniline
on nitration gives a substantial amount of m-nitroaniline.
36. An organic compound A (C2H3N) is used as a solvent of choice for many organic reactions
because it is not reactive in mild acidic and basic conditions. Compound A on treatment with Ni/H2
forms B. When B is treated with nitrous acid at 273 K, ethanol is obtained. When B is warmed with
chloroform and NaOH , a foul smelling compound C formed. Identify A, B and C.
37. An organic compound AA C3H6O2  on reaction with ammonia followed by heating yield B.
Compound B on reaction with Br2  and alc. NaOH  gives compound C (C2H7N). Compound C forms a
foul smelling compound D on reaction with chloroform and NaOH . Identify A, B, C, D and the write
the equations of reactions involved.