HB Classes:

DPS –4 (ORGANIC) AMINES CLASS: 10+2 DATE: AUGUST 2024

Q1. 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

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Q2. 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 hydrates 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

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 (vii) Gabriel phthalimide synthesis is preferred for synthesizing primary amines.

Q3. 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

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 (vi) In increasing order of solubility in water:
C6H5NH2, (C2H5)2NH, C2H5NH2

Q4. 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

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 (vii) Nitromethane into dimethylamine

(viii) Propanoic acid into ethanoic acid?

Q5. Describe a method for the identification of primary, secondary and tertiary amines. Also write chemical equations of the
reactions involved.

Q6. Write short notes on the following:

(i) Carbylamine reaction

(ii) Diazotisation

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 (iii) Hoffmann’s bromamide reaction

(iv) Coupling reaction

(v) Ammonolysis

(vi) Acetylation

Q7. Accomplish the following conversions:

(i) Nitrobenzene to benzoic acid

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(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

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 (vii) Aniline to p-bromoaniline

(viii) Benzamide to toluene

(ix) Aniline to benzyl alcohol

Q8. Give the structures of A, B and C in the following reactions:

−
(i) CH3CH2I ⎯NaCN
⎯⎯→ A ⎯⎯ ⎯OH⎯ ⎯ ⎯ ⎯+Br
⎯→ B ⎯NaOH ⎯2→ C
Partial hydrolysis

+
(ii) ⎯ ⎯→ A ⎯H⎯
C6H5N2Cl ⎯CuCN ⎯ ⎯→ B ⎯NH
2O / H
⎯→
⎯3


(iii) ⎯→ ⎯⎯4→ B ⎯HNO

⎯ A ⎯LiAlH
CH3CH2Br ⎯KCN ⎯o⎯2→ C
0 C

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 +
(iv) C6H5NO2 ⎯Fe⎯/ HCl ⎯⎯2 +⎯
⎯→ A ⎯NaNO HCl
⎯→ B ⎯H⎯
2O / H
⎯ ⎯→ C
273K 

(v) CH3COOH ⎯NH

⎯→ ⎯⎯→ B ⎯NaNO
⎯3 A ⎯NaOBr ⎯ ⎯2 /⎯
HCl
⎯→ C


⎯→ A ⎯HNO
C6H5OH
(vi) C6H5NO2 ⎯Fe⎯/ HCl ⎯⎯2→ B ⎯⎯ ⎯⎯→
273K

Q9. 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 C5H7N. Write the structures and IUPAC names of compounds A, B and C.

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Q10. 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)2O →

( i ) HBF4
(vii) C6H5N2Cl ⎯⎯ ⎯ ⎯ ⎯ ⎯⎯→
( ii ) NaNO3 / Cu , 

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Q11. Why cannot aromatic primary amines be preprared by Gabriel phthalimide synthesis?

Q12. Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid.

Q13. Give plausible explanation for each of the following:

(i) Why are amines less acidic than alcohols of comparable molecular masses?

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 (ii) Why do primary amines have higher boiling points than tertiary amines?

(iii) Why are aliphatic amines stronger bases than aromatic amines?

Q14. Identify A and B in the following sequence:

CH3COOC 2H5 ⎯NH
⎯3 A ⎯Br
⎯→ ⎯ 2 / KOH
⎯⎯→ B

Q15. Write the chemical reaction occurring in the preparation of fluorobenzene from aniline.

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Q16. Complete the following equation:
C6H5NH2 + Br2(aq) ⎯
⎯→

Q17. Convert aniline to phenylisocyanide.

Q18. Convert aniline to sulphanilic acid.

Q19. Give the chemical tests to distinguish between the following pairs of compounds:
(i) Ethylamine and Aniline

(ii) Aniline and Benzylamine

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Q20. Show the mechanism of acetylation of ethanamine and write the IUPAC name of the product formed.

Q21. Write a chemical equation each to represent

(i) Gatterman reaction

(ii) Carbylamine reaction

Q22. Write the names associated with the following reactions:

(a) RCONH2 + Br2 + 4NaOH ⎯
⎯→ RNH2 + Na2CO3 + 2NaBr + 2H2O

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 (b) ArN2+X− ⎯CuCN
⎯⎯ / KCN
⎯⎯→ ArCN + N2

(c) R – NH2 + CHCl3 + 3KOH ⎯Heat

⎯⎯→ R – NC + 3KCl + 3H2O

(d) ArN2+X− ⎯Cu

⎯/ ⎯
HCl
⎯→ ArCl + N2 + CuX

Q23. How will you distinguish between:

NH2

(a) and CH3NH2

(b) CH3 − N− H and (CH3 )3 N

|
CH3

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Q24. (a) How can you convert an amide into an amine having one carbon less than the starting compound?

(b) Name the reaction.

(c) Give the IUPAC name the structure of the amine obtained by the above method if the amide is 3-chlorobutanamide.

Q25. Account for the following:

(a) Aniline does not undergo Friedel Crafts alkylation.

(b) Although −NH2 group is an ortho and para-directing group, nitration of aniline gives along with ortho and para-derivatives,
meta-derivative also.

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