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Chapter 13

Amines

Solutions

SECTION - A
Objective Type Questions
(Classification and Nomenclature of Amines)

CH3
H
1. CH3 C N is a
H
CH3

(1) Primary amine (2) Secondary amine (3) Tertiary amine (4) Ammonium salt
Sol. Answer (1)

NH2

This is primary amine.

2. The correct IUPAC name for


CH2 CH CH2 NH CH3 is
(1) Allyl methylamine (2) 2-Amino4-pentene
(3) 4-Aminopent-I -ene (4) N-Methylprop-2-en-1-amine
Sol. Answer (4)

NH
CH3
N-methyl prop-2-ene 1-amine

3. The compound having the molecular formula C3H9N can represent


(1) Trimethylamine (2) n-propylamine (3) Isopropylamine (4) All of these
Sol. Answer (4)
C3H9N may be trimethylamine or n-propylamine or may be isopropylamine.
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4. A secondary amine is
(1) A compound with two –NH2 group
(2) A compound with two carbon atoms and a –NH2 group
(3) A compound with a –NH2 group on the carbon atom in number two position
(4) A compound in which two of the hydrogens of NH3 have been replaced by alkyl or aryl groups
Sol. Answer (4)

CH 3 – N – CH 3  is secondary amine.
H
(Preparation of Amines)

5. Hoffmann bromamide degradation reaction is shown by


(1) Ar – NH2 (2) Ar – CONH2 (3) Ar – NO2 (4) Ar – CH2NH2
Sol. Answer (2)

O
C – NH2 will show Hoffmann degradation reaction.

6. Best method for preparing primary amines from alkyl halides without changing the number of carbon atoms
in the chain is
(1) Hoffmann bromamide reaction (2) Gabriel phthalimide synthesis
(3) Sandmeyer reaction (4) Reaction with NH3
Sol. Answer (2)
1° amine can be prepared by Gabriel phthalimide reaction

7. Gabriel phthalimide reaction is used for the preparation of


(1) Primary aromatic amines (2) Secondary amines
(3) Aliphatic primary amines (4) Tertiary amines
Sol. Answer (3)
Gabreil pathalmide reaction  1° primary amine

8. When acetamide is treated with Br2 and caustic soda, then we get
(1) Bromoacetic acid (2) Acetic acid (3) Methylamine (4) Ethane
Sol. Answer (3)
O

Br21OH
CH 3 – C – NH 2 CH 3 – NH 2

Reduction
9. CONH2   CH2NH2
In above reaction hybridisation state of carbon changes from
2 3
(1) sp sp (2) sp sp (3) sp2 sp
3
(4) sp2 sp
Sol. Answer (3)
O
Reduction
– C – NH2 – CH2NH2
2 2
sp sp

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Solutions of Assignment (Set-2) Amines 229
10. A compound ‘A’ when treated with HNO3 (in presence of H2SO4) gives compound B, which is then reduced
with Sn and HCl to aniline. The compound is
(1) Toluene (2) Benzene (3) Ethane (4) Acetamide
Sol. Answer (2)

Nitration Sn/4HCl
NO2 NH2
(Benzene) (Aniline)

(Physical and Chemical Properties)

11. Amines are basic in character because they have


(1) A lone pair of electrons on the nitrogen atom (2) A hydroxyl group in the molecule
(3) Replaceable hydrogen atom (4) Saturated C atom
Sol. Answer (1)
:

R – NH2 because of low pair of electron amines are basic

12. Which is most basic?


(1) Benzylamine (2) Aniline (3) Acetamide (4) o-methyl aniline
Sol. Answer (1)

most basic, no conjugation (lone pair not in conjugation)


:

NH2

13. Aliphatic amines are ______ basic than NH3 but aromatic amines are ______ basic than NH3.
(1) More, less (2) Less, more (3) More, more (4) None of these
Sol. Answer (1)
Because in aromatic amine lone pair is in conjugation with benzene ring.

14. Amongst the following, the strongest base in aqueous medium is


(1) CH3NH2 (2) (CH3)3N (3) (CH3)2NH (4) C6H5NHCH3
Sol. Answer (3)
(Me)2NH > MeNH3 > (Me)3N > Ph(Me)2N (Me = methyl)

15. Which of the following is the weakest Bronsted base?


NH2 NH2

(1) (2) (3) (4) CH3NH2


N
Sol. Answer (1) H
+ + +
:

NH2 NH2 NH2 NH2 NH2

one pair on nitrogen in conjugation.

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16. The correct increasing order of basic strength for the following compounds is
NH2 NH2 NH2

NO2 CH3
(I) (II) (III)
(1) II < III < I (2) III < I < II (3) III < II < I (4) II < I < III
Sol. Answer (4)
NH2 NH2 NH2

CH3 NO2
(+H) (–M)
Basic strength

17. Which of the following is the least basic?

NH2 NH2 NH2

(1) (2) (3) (4) All are equally basic

NO2 OCH3 C6H5


Sol. Answer (1)
NH2

is least basic because of presence of –I & –R (–NO2) group.

NO2

18. The decreasing order of the basic character of NH3, CH3NH2, C2H5NH2 and C6H5NH2 is
(1) NH3 > CH3NH2 > C2H5NH2 > C6H5NH2 (2) C2H5NH2 > CH3NH2 > NH3 > C6H5NH2
(3) C6H5NH2 > C2H5NH2 > CH3NH2 > NH3 (4) CH3NH2 > C2H5NH2 > C6H5NH2 > NH3
Sol. Answer (2)

NH2 CH3 NH2 NH3 NH2

19. The one which is the least basic


(1) NH3 (2) C6H5NH2 (3) (C6H5)3N (4) (C6H5)2NH
Sol. Answer (3)
:

N
is least basic

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20. Strongest base is
(1) CH2 = CH – CH2 – NH2 (2) CH  C – CH2 – NH2
NH2

(3) CH3CH2CH2NH2 (4)

Sol. Answer (3)

NH2 is the strongest base among the other shown bases because of max e– density over N-atom.

21. CH3CH2NH2 is more basic than CH3CONH2 because


(1) Acetamide is amphoteric in character
(2) In CH3CH2NH2 the electron pair on N-atom is delocalised by resonance
(3) In CH3CH2NH2 there is no resonance, while in acetamide the lone pair of electrons on N-atom is
delocalised and therefore less available for protonation
(4) Acetamide is derivative of acid
Sol. Answer (3)
Lone pair of nitrogen in conjugation with  bond i.e., ( –LP conjugation)
O O
+
:

NH2 NH2
NH2
resonance

22. Which one is the most volatile?

CH2
(1) CH3CH2CH2NH2 (2) (CH3)3N (3) NH (4) CH3OH
CH 3

Sol. Answer (2)

CH3
N is most volatile in above choices
CH3 CH3

23. Aniline on reaction with acetyl chloride gives


(1) Phenol (2) Acetamide (3) Acetanilide (4) Benzene
Sol. Answer (3)

O O
NH2+ NH–C–CH3
Cl acetanilide

24. The compound obtained by heating a mixture of a primary amine and chloroform with ethanolic potassium
hydroxide is
(1) An alkyl isocyanide (2) An alkyl halide
(3) An amide (4) An amide and nitro compound

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Sol. Answer (1)

OH−

R – NH2 + CHCl3 ⎯⎯⎯ → R − N= C

alkyl isocyanide
25. A compound X has the molecular formula C7H7NO. On treatment with Br2 and KOH, X gives an amine Y.
The latter gives carbylamine test. Y upon diazotisation and coupling with phenol gives an azo dye. Thus X
is
(1) C6H5CONH2 (2) C6H5CH2NO (3) C6H5COONH4 (4) All of these
Sol. Answer (1)
O
C – NH2 – Br2, OH– NH2
Y

N= C CHCl3, OH

26. An organic compound (A) on reduction gave a compound (B). Upon treatment with HNO2, (B) gave ethyl
alcohol and on warming with CHCl3 and alcoholic KOH, (B) gave an offensive smell. The compound (A) is
(1) CH3NH2 (2) CH3NC (3) CH3CN (4) C2H5CN
Sol. Answer (3)
[H] HONO
CH3CN NH2 OH

CHCl3, OH

CH3–CH2–N =C

27. An amine reacts with C6H5SO2Cl and the product is soluble in alkali, amine is
(1) 1° amine (2) 2° amine (3) 3° amine (4) All of these
Sol. Answer (1)
O O
R–NH2 + Cl–S– R–N–S–
(1°)
O H O
Base
Soluble

28. Which would not react with benzene sulphonyl chloride in aqueous NaOH?
(1) Aniline (2) N, N-dimethylaniline (3) p-toluidine (4) N-ethyl aniline
Sol. Answer (2)

Me O
N + Cl–S Because of lack of H on nitrogen.
Me
O
No reaction

29. A mixture of 1°, 2° and 3° amines can be separated by Hinsberg’s reagent which is
(1) Benzoyl chloride (2) Acetyl chloride
(3) Benzene sulphonyl chloride (4) Benzyl chloride

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Sol. Answer (3)
Hinsberg's reagent
O
–S–Cl
O
Benzene sulphonyl chloride

30. Bromine water reacts with aniline to give


(1) o-Bromoaniline (2) m-Bromoaniline
(3) p-Bromoaniline (4) 2, 4, 6-Tribromoaniline
Sol. Answer (4)
Br
H2O
–NH2 + Br2  Br – NH2
Br
(2, 4,6 Tribromo anilne)
31. Identify X in the series.

NHCOCH3

HNO3 H2O
Intermediate X
H2SO4 

NH2 NH2 NHCOCH3 NH2


NO2
(1) (2) (3) (4)

NH2 NO2 NO2 NO2

Sol. Answer (2)

O
NH–C–CH3 NH–C–CH3 NH2
O Nitration H2O

NO2

32. 2, 4, 6-tribromo aniline is a product of

(1) Electrophilic addition on C6H5NH2 (2) Electrophilic substitution on C6H5NH2

(3) Nucleophilic addition on C6H5NH2 (4) Nucleophilic substitution on C6H5NH2

Sol. Answer (2)

Br
H2O
–NH2 + Br2  Br – NH2
Br

(2, 4,6 Tribromo aniline)


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33. Amines are highly soluble in


(1) CCl4 (2) Diethyl ether (3) Benzene (4) Water
Sol. Answer (4)
Amines are highly soluble in H2O because of hydrogen bonding.
34. Which one of the following compounds gives dye test?
(1) Aniline (2) Methylamine (3) Diphenylamine (4) Ethylamine
Sol. Answer (1)
Aniline gives a dye test.

35. The strongest ortho-para and strongest meta directing groups are respectively
(1) –NO2 and –NH2 (2) –CONH2 and –NH2 (3) –NH2 and –NO2 (4) –NH2 and CONH2
Sol. Answer (3)
– NH2  Strongest o/p directing because of + R nature
– NO2  Strongest m directing because of – R nature
(Diazonium Salts, Cyanides and Isocyanides)

36. Which of the following forms a stable diazonium salt at 273 - 278 K?
(1) Ethylamine (2) Aniline (3) Dimethylamine (4) Benzylamine
Sol. Answer (2)
NaNO2 , dil HCl
NH2 N2+Cl–
O–5°C

37. Reaction of nitrous acid with aliphatic primary amine in the cold gives
(1) A diazonium salt (2) An alcohol (3) A nitrite (4) A dye
Sol. Answer (2)
R–NH2 + HONO  R–OH
(Alcohol)

38. The gas evolved when methylamine reacts with nitrous acid is
(1) NH3 (2) N2 (3) H2 (4) C2H6
Sol. Answer (2)
CH3NH2 + 2HNO2  C-H3–O–N =O + N2 + H2O
Methyl nitrite
2CH3NH2 + 2HNO2  CH3–O–CH3 + 2N2 + 3 H2O
Methoxy methane
1° Amine reacts with nitrous acid to form alcohol except methyl amine at ordinary temperature.

39. Tautomerism is shown by

(1) CH3 – O – NO (2) CH3 – CH2 – NO2 (3) CH3CH2CN (4) CH3 – CH – CH
CH3
Sol. Answer (2)
O OH
CH3 – CH2 – N CH3 – CH = N
O O
Nitro form Aci form
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40. Benzenediazonium chloride on reaction with water gives
(1) Phenol (2) Aniline (3) Benzylamine (4) Benzaldehyde
Sol. Answer (1)

N2+Cl– + H2O OH

41. Benzenediazonium chloride on reaction with phenol in weakly basic medium gives
(1) Diphenyl ether (2) p-Hydroxyazobenzene (3) Chlorobenzene (4) Benzene
Sol. Answer (2)
OH

+ – OH
N2 Cl + OH

N
N

42. When benzenediazonium chloride is heated with fluoro boric acid, fluorobenzene is formed. This reaction is
called
(1) Balz Schiemann reaction (2) Gattermann reaction
(3) Sandmeyer reaction (4) Hofmann bromamide reaction
Sol. Answer (1)

+ – + – 
N2 Cl + H BF4 F

This is Balz Schiemann reaction.

43. Benzenediazonium chloride is reduced to benzene by


(1) Water (2) Hypophosphorous acid (3) Hypophosphoric acid (4) Phosphine
Sol. Answer (2)

+
N2 Cl– + H3PO2

(Benzene)

44. Diazotisation can be carried out by the action of NaNO2 and dilute HCI at ice cold temperature
(1) Aromatic secondary amine
(2) Aromatic primary amine
(3) Aromatic nitro compound
(4) Aliphatic amine
Sol. Answer (2)

O–5°C
NH2 + HONO NH2+ C–

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45. When benzene diazonium chloride is treated with cuprous chloride and HCI the product formed is
(1) Chlorobenzene (2) Benzene

(3) Phenol (4) Chloroazobenzene

Sol. Answer (1)

HCl
N2+Cl– + Cu2Cl2 Cl (Sandmeyr's reaction)

46. The end product (Z) of the following reaction is

+ –
N2 Cl

CuCN Complete hydrolysis NaOH


(X) (Y) CaO, 
(Z)

(1) A cyanide (2) A carboxylic acid (3) An amine (4) An arene


Sol. Answer (4)

N2+Cl– CN COOH
+
CuCN H NaOH
H2O Cao, 

(X) (Y) (An arene)

SECTION - B
Objective Type Questions
(Preparation of Amines)

1. Which one of the following on reduction with lithium aluminium hydride yields a secondary amine?

(1) Methyl isocyanide (2) Acetamide (3) Methyl cyanide (4) Nitroethane
Sol. Answer (1)
Me
CH3N = C + LiAlH4 NH
Me
(2°) amine

2. The reaction of the benzyl chloride with sodium cyanide followed by reduction with hydrogen in the presence of
nickel gives
(1) -phenyl ethylamine (2) N-isobutylaniline (3) Benzyl amine (4) Aniline
Sol. Answer (1)

– [H] 
+ CN
Cl CN  NH2
(-phenyl
ethylamine)

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3. Amine is obtained as major product in

CH3
NH3 NaNH2
(1) Cl (2) CH3 CH2 CH CH3 NH3

O Cl
LiAlH4
(3) CH 3 C NH CH3 (4) All of these

Sol. Answer (3)


O
LiA/H4
CH3 – C – NH – CH3 CH3– CH2 – NH – CH3
(port)

4. N-phenyl hydroxylamine is obtained when nitro benzene is reacted with

(1) Sn/HCl (2) Zn/NH4Cl/H2O (3) As2O3/NaOH (4) Zn/NaOH

Sol. Answer (2)

NO2 Zn/NH4 Cl N-phenyl


hydroxylamine

KOH R—X NH2NH 2/ethanol


5. NH (A) (B) (C) + R—NH2 .

The product (C) is

O O
COOH CO C
NH O
(1) (2) NH (3) (4)
COOH CO C NH NH

O O

Sol. Answer (3)


O O

OH
NH N–R
R-X

O O
+ NH2NH2, EtOH

O
NH
R – NH2 +
NH
O

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6. When methyl iodide treated with ammonia, the product obtained is


(1) Methyl amine (2) Dimethyl amine (3) Trimethyl amine (4) All of these
Sol. Answer (4)
+ +
CH3I + NH3  CH3NH2 + NH (CH3)2 + I N (CH3)4 + N (CH3)3

7. C7H9N has how many isomeric forms that contain a benzene ring?
(1) 4 (2) 5 (3) 6 (4) 7
Sol. Answer (2)
NH2
NH2 NH2

CH3
CH3 CH3
NH – CH3 CH2 – NH2

Hence, there are '5' possible ways.


(Physical and Chemical Properties)

8. R–NH 2 + CH 3COCl A.
(excess)

The product (A) will be

(1) RNHCOCH3 (2) RN(COCH3)2 (3) RN(COCH3)3Cl– (4) R–CONH2

Sol. Answer (1)

O O
R–NH2+CH3–C–Cl R–NH–C–CH3

9. Arrange the following compound in decreasing order of boiling point


(1) (CH3)3N < CH3NHC2H5 < C3H7NH2 < C3H7OH (2) (CH3)3N < C3H7NH2 < C3H7OH < CH3NHC2H5
(3) C3H7NH2 < CH3NHC2H5 < (CH3)3N < C3H7OH (4) (CH3)3N < CH3NHC2H5 < C3H7OH < CH3H7NH2
Sol. Answer (1)

(CH3 )3 N < CH3NHC2H5 < C3H7NH2 < C3H7OH


Boiling point order

10. Alanine, the amino acid the respective structure at pH = 2 and pH = 10 will be

CH3 CH 3 CH3 CH3


+ + –
+

(1) NH2– CH – COO , H 3 N – CH – COOH (2) H3 N – CH – COO , H3 N – CH – COOH

CH3 CH3 CH3 CH3


+ +
(3) H3 N – CH – COOH , NH2 – CH – COO (4) NH 2 – CH – COO , H3N – CH – COO

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Sol. Answer (3)

CH3
+
At PH = 2 : H3N – CH – COOH

CH3
At PH = 10 : NH2 – CH – COO–

11. Which product is formed, when acetonitrile is hydrolysed partially with cold concentrated HCl?
(1) Methyl cyanide (2) Acetic anhydrides
(3) Acetic acid (4) Acetamide
Sol. Answer (4)
O
partially
CH3CN + H2O CH3 – C – NH2

12. Which of the following pair make fastest coupling reaction in acidic medium?

OH N2Cl NH2 N2Cl OH N2Cl OCH3 N2Cl

(1) , (2) , (3) , (4) ,

NH2 NO2 NO2 NH2

Sol. Answer (2)


NH2 NH2

NO2 N2+Cl– +

N
N

NO2

13. Which of the following statements about primary amines is ‘False’?


(1) Alkyl amines are stronger bases than ammonia
(2) Alkyl amines are stronger bases than aryl amines
(3) Alkyl amines react with nitrous acid to produce alcohols
(4) Aryl amines react with nitrous acid to produce phenols
Sol. Answer (4)

+ –
NH2 + HONO N2 Cl
(Stable)

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14. The most reactive compound towards Hofmann bromamide degradation is

CONH2 CONH2

(1) (2)

NO2 OCH3

CONH2 CONH2

(3) (4)

CH3 Cl

Sol. Answer (2)

COCH3

is most reactive because the Migration step is RDS step and assisted by (+M) of –OCH3 at p-
OCH3
position.

NO2
+
KCN H2O/H
A B
15. .

Br

The major product (B) is

NO2 COOH
NO2 COOH

(1) (2) (3) (4)

COOH COOH Br Br

Sol. Answer (3)

NO2
+
KCN H2O/H
A B

COOH

COOH

B is
Br

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Mechanism

16. Benzylamine and aniline can be distinguish by

(1) HNO2 acid (2) CHCl3 /KOH (3) Br2 water (4) Schiff ’s reagent

Sol. Answer (3)

NH2
NH2

Distinguished by Br2, H2O

17. 4-Nitro-N, N-dimethyl benzenamine is

N(CH 3)2 NH2 N(CH3)2 N(C2H5)2

(1) (2) (3) (4)


NO2 CH3
NO2 NO2 NO2

Sol. Answer (3)

CH3 CH3
N
1
2

3 4-Nitro-N, N-dimethyl benzene amine


4
NO2
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NO2
(NH4)2S NaNO2 /
18. (A) (B)
HCl, 0ºC
NO2
H3O+ CuCN/
(D) (C)
HCN
The above reaction sequence (D) is

CN COOH COOH COOH

(1) (2) (3) (4)

NO2 NO2 NH2 COOH


Sol. Answer (2)
COOH

NO2

N(CH3)2

HNO2
19. A . The product A will be

N(CH3)2 N(CH3)2
NO2 O=N–NCH3

(1) (2) (3) (4)


NO2 N=O
Sol. Answer (4)
CH3 CH 3
N HONO O=N N
CH3 CH 3
(A )

20. Write the correct order of the following diazonium cations for the coupling with phenol
N2+ N2+ N2+ N2+

OCH3
CH3 NO2
I II III IV
(1) III > IV > I > II (2) II > I > IV > III (3) III > I > II > IV (4) II > IV > I > III
Sol. Answer (1)
The order of reactivity for coupling with phenol is
+ + + +
N2 N2 N2 N2

OCH3
NO2 CH3
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SECTION - C

Previous Years Questions

1. Nitration of aniline in strong acidic medium also gives m-nitroaniline because [NEET-2018]
(1) Inspite of substituents nitro group always goes to only m-position.
(2) In electrophilic substitution reactions amino group is meta directive.
(3) In acidic (strong) medium aniline is present as anilinium ion.
(4) In absence of substituents nitro group always goes to m-position.
Sol. Answer (3)

NH2 NH3

Anilinium ion

–NH3 is m-directing, hence besides para (51%) and ortho (2%), meta product (47%) is also formed in
significant yield.
2. The correct increasing order of basic strength for the following compounds is [NEET-2017]

NH2 NH2 NH2

NO2 CH3
(I) (II) (III)

(1) II < III < I (2) III < I < II (3) III < II < I (4) II < I < III
Sol. Answer (4)
–NO2 has strong –R effect and –CH3 shows +R effect.
 Order of basic strength is

NH2 NH2 NH2

< <

NO2 CH3

3. Which of the following reactions is appropriate for converting acetamide to methanamine? [NEET-2017]
(1) Carbylamine reaction (2) Hoffmann hypobromamide reaction
(3) Stephens reaction (4) Gabriels phthalimide synthesis
Sol. Answer (2)
O

CH3 – C – NH2 + Br2 + 4NaOH CH3 – NH2 + 2NaBr + Na2CO3 + 3H2O
This is Hoffmann Bromamide reaction.
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4. Which one of the following nitro-compounds does not react with nitrous acid? [NEET-(Phase-2)-2016]

H2 H2 CH3
H3C C H3C C H3C
(1) C NO2 (2) CH NO2 (3) H3C C NO2 (4) H3C C
H2 H3C H NO2
H3C
O
Sol. Answer (3)

CH3
H3C C NO2
CH3
No acidic H-atom on the carbon atom having NO2-group.
5. A given nitrogen-containing aromatic compound A reacts with Sn/HCl, followed by HNO2 to give an unstable
compound B. B, on treatment with phenol, forms a beautiful coloured compound C with the molecular formula
C12H10N2O. The structure of compound A is [NEET-(Phase-2)-2016]

NH2 NO2 CN CONH2


(1) (2) (3) (4)

Sol. Answer (2)

OH

NO2 NH2 N2Cl


Sn/HCl HNO2
N=N OH

6. The product formed by the reaction of an aldehyde with a primary amine is [NEET-2016]
(1) Aromatic acid (2) Schiff base (3) Ketone (4) Carboxylic acid
Sol. Answer (2)

O H
R C H + RNH2 R C N R+ H2O
schiff base

7. The correct statement regarding the basicity of arylamines is [NEET-2016]


(1) Arylamines are generally more basic than alkylamines, because the nitrogen atom in arylamines is sp-
hybridized
(2) Arylamines are generally less basic than alkylamines because the nitrogen lone-pair electrons are
delocalized by interaction with the aromatic ring  electron system
(3) Arylamines are generally more basic than alkylamines because the nitrogen lone-pair electrons are not
delocalized by interaction with the aromatic ring  electron system
(4) Arylamines are generally more basic than alkylamines because of aryl group
Sol. Answer (2)

NH2

R NH2

Arylamine Alkyl amine


(less basic) (more basic)
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8. The following reaction
H
NH2 N
NaOH
+ Cl
O
O
is known by the name [Re-AIPMT -2015]
(1) Acetylation reaction (2) Schotten-Baumen reaction
(3) Friedel-Craft’s reaction (4) Perkin’s reaction
Sol. Answer (2)
The synthesis of amides from amines with acyl halides or anhydrides in the presence of aqueous base is known
as the Schotten-Baumann reaction.

9. Method by which Aniline cannot be prepared is [Re-AIPMT-2015]


(1) Reduction of nitrobenzene with H2/Pd in ethanol
(2) Potassium salt of phthalimide treated with chlorobenzene followed by hydrolysis with aqueous NaOH
solution
(3) Hydrolysis of phenylisocyanide with acidic solution
(4) Degradation of benzamide with bromine in alkaline solution
Sol. Answer (2)

Cl

Does not undergo nucleophilic substitution under normal conditions.

10. The electrolytic reduction of nitrobenzene in strongly acidic medium produces [AIPMT-2015]
(1) Aniline (2) p-Aminophenol (3) Azoxybenzene (4) Azobenzene
Sol. Answer (2)
OH

Strongly acidic Rearrangement


NO2 medium
NH OH

NH2
(p-Aminophenol)

11. In the following reaction, the product (A)


+
NNCl

NH2
+
H (A) is [AIPMT-2014]
+
yellow dye

NH 2
(1) N=N–NH (2) N=N

NH2
(3) N=N (4) N=N NH2

Sol. Answer (4)


+
H
N  NCl + H
+
NH2 –HCl NH = N NH2

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246 Amines Solutions of Assignment (Set-2)

 –
12. Which of the following will be most stable diazonium salt RN2 X ? [AIPMT-2014]
 –
(1) CH3N2 X (2) C6H5N2 X– (3) CH3 CH2 N2 X– (4) C H CH N2 X–
6 5 2

Sol. Answer (2)


Aliphatic diazonium salts decompose on room temperature to form carbocations. Aromatic diazonium salt are
stable. So answer is (2).

13. Nitrobenzene on reaction with conc. HNO3/H2SO4 at 80–100°C forms which one of the following products?
[NEET-2013]
(1) 1,3-Dinitrobenzene (2) 1,4-Dinitrobenzene (3) 1,2,4-Trinitrobenzene (4) 1,2-Dinitrobenzene
Sol. Answer (1)
NO2
NO 2
A
14. In the reaction Br 
+ Br
N2Cl
A is [NEET-2013]
+
(1) Cu2Cl2 (2) H3PO2 and H2O (3) H /H2O (4) HgSO4/H2SO4
Sol. Answer (2)

15. An organic compound (C3H9N) (A), when treated with nitrous acid, gave an alcohol and N2 gas was evolved.
(A) on warming with CHCl3 and caustic potash gave (C) which on reduction gave isopropylmethylamine. Predict
the structure of (A) [AIPMT (Mains)-2012]
CH 3
(1) CH–NH2 (2) CH3CH2–NH–CH3 (3) CH 3–N–CH 3 (4) CH3CH2CH2–NH2
CH3
Sol. Answer (1) CH3

CH3
CH – NH2
CH3

NO2
Zn
16. What is the product obtained in the following reaction: 
NH Cl
 ...........?
4

[AIPMT (Prelims)-2011]
NH2 NHOH
(1) (2)


N O

(3) N (4) N=N


+

Sol. Answer (2)


Zn
NO2 NH4Cl
NH OH

N-phenylhydroxylamine

17. Which of the following compounds is most basic ? [AIPMT (Mains)-2011]

(1) N COCH 3(2) NH2 (3) O 2N NH2 (4) CH2NH2


H
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Solutions of Assignment (Set-2) Amines 247
Sol. Answer (4)
Lone pair of N does not involve in resonance with benzene ring.

18. Acetamide is treated with the following reagents separately. Which one of these would yield methylamine?
[AIPMT (Prelims)-2010]
(1) NaOH – Br2 (2) Sodalime (3) Hot conc. H2SO4 (4) PCl5
Sol. Answer (1)
O
Br2/OH
CH3 NH2 CH3 – NH2

19. Which of the following statements about primary amines is 'False'? [AIPMT (Prelims) -2010]
(1) Alkyl amines are stronger bases than aryl amines
(2) Alkyl amines react with nitrous acid to produce alcohols
(3) Aryl amines react with nitrous acid to produce phenols
(4) Alkyl amines are stronger bases than ammonia
Sol. Answer (3)
Aryl amines react with nitrous acid to form diazonium salt.

20. Aniline in a set of the following reactions yielded a coloured product 'Y'
NH2

NaNO2/HCl N, N-dimethylaniline
X Y
(273 – 278K)
The structure of 'Y' would be [AIPMT (Prelims)-2010]
CH3 CH3
CH3
(1) N=N N (2) HN NH NH
CH3
CH3 CH3

(3) H 3C N=N NH2 (4) HN N=N NH


Sol. Answer (1)
Ml
Y is a pot of coupling reaction i.e., N=N N
Ml

21. Match the compounds given in Column-I with their characteristic reactions given in Column-II. Select the correct
option
Column-I Column-II
(Compounds) (Reactions)
a. CH3CH2CH2CH2NH2 (i) Alkaline hydrolysis
b. CH3C  CH (ii) With KOH (alcohol) and CHCl3 produces bad smell
c. CH3CH2COOCH3 (iii) Gives white ppt. with ammoniacal AgNO3
d. CH3CH(OH)CH3 (iv) With Lucas reagent cloudiness appears after 5 minutes
[AIPMT (Mains)-2010]
(1) a(ii), b(i), c(iv), d(iii) (2) a(iii), b(ii), c(i), d(iv) (3) a(ii), b(iii), c(i), d(iv) (4) a(iv), b(ii), c(iii), d(i)

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248 Amines Solutions of Assignment (Set-2)

Sol. Answer (3)


a  (ii)

KOH CHCl
H3C  CH2  CH2  CH2  NH2 
3

 H3C  CH2  CH2  CH2  NC

It reacts with KOH (alcohol) and CHCl3 produces (1° R – NH2) bad smell (isocyanide)
b  (iii)

AgNO
H3C  C  C  H 3
 H3C  C  C  Ag  HNO3
  White ppt.
acidic‘H’

c  (i)

NaOH(aq.)
H3C CH2 C OCH3 H3C CH2 C OH + H3COH
d  (iv)

H3C CH CH3 gives test with Lucas reagent cloudiness appears after 5 minutes.

22. Predict the product

NHCH 3 + NaNO2+HCl Product [AIPMT (Prelims)-2009]

CH3 NHCH3 NHCH3 OH CH3


N – NO2 NO N– CH3 N– N = O
(1) (2) + (3) (4)
NO

Sol. Answer (4)

H CH 3
N + HONO N
CH3 N=O

23. In a reaction of aniline a coloured product C was obtained


CH3
NH2 N
NaNO2 CH3
B C
HCl Cold
A
The structure of C would be [AIPMT (Prelims)-2008]

CH3
(1) N=N N (2) N=N CH2–N
CH3
CH2

CH3 CH3
CH3
N=N NH=NH N
(3) (4) CH3

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Solutions of Assignment (Set-2) Amines 249
Sol. Answer (1)
CH3 CH3

CH3 N
N
CH3
HONO +
NH2 N2

24. Which one of the following on reduction with lithium aluminium hydride yields a secondary amine ?
[AIPMT (Prelims)-2007]
(1) Methyl cyanide (2) Nitroethane (3) Methylisocyanide (4) Acetamide
Sol. Answer (3)

25. Which of the following is more basic than aniline ? [AIPMT (Prelims)-2006]
(1) Diphenylamine (2) Triphenylamine (3) p-Nitroaniline (4) Benzylamine
Sol. Answer (4)

26. Aniline in a set of reactions yielded a product D.


NH2 NaNO CuCN H HNO

HCl
2
 A   B 
2
Ni
 C 
2
D

The structure of the product D would be [AIPMT (Prelims)-2005]

(1) C6H5CH2NH2 (2) C6H5NHCH2CH3 (3) C6H5NHOH (4) C6H5CH2OH


Sol. Answer (4)
Br
NH2 HONO
N2+ CuCN CN H2 CH2N2 HONO
OH
(A) (B) (C) (D)

27. The major organic product formed from the following reaction
O
(i) CH3NH2

(ii) LiAIH (iii) H O
 ......... is [AIPMT (Prelims)-2005]
4 2

CH3 O–NHCH3 NHCH3


(1) (2) (3) (4)
OH NHCH3 OH OH

Sol. Answer (2)


CH3 O CH3 N – CH3 CH3 NHCH3
C CH3, NH2 C LiAlH4,H2O C
CH3 CH3 CH3 CH3 CH3 CH3

28. Electrolytic reduction of Nitrobenzene in weakly acidic medium gives [AIPMT (Prelims)-2005]
(1) Aniline (2) Nitrosobenzene
(3) N-phenylhydroxylamine (4) p-Hydroxyaniline

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250 Amines Solutions of Assignment (Set-2)

Sol. Answer (1)


SN/HCl
NO2 NH2

29. Which of the following is most basic in a solution of carbon tetrachloride?


(1) NH3 (2) CH3CH2NH2 (3) (CH3CH2)2NH (4) (CH3CH2)3N
Sol. Answer (4)
N(Et)3
Triethylamine must be most basic in CCl4 solution.

30. What will be the final product in the following reaction sequence?
 NH
H /H2O
 A   B 
3 NaOBr
CH3CH2CN   C

(1) CH3CH2CONH2 (2) CH3CH2COBr (3) CH3CH2NH2 (4) CH3CH2CH2NH2


Sol. Answer (3)
H +, H2O NH3 NaOBr
CN COOH 
CONH2 NH2

31. The action of nitrous acid on an aliphatic primary amine, gives


(1) Secondary amine (2) Nitroalkane (3) Alcohol (4) Alkyl nitrite
Sol. Answer (3)
(aq)
R – NH2 + HONO  R – N2  R – OH + N2
+

32. The compound obtained by heating a mixture of ethyl amine and chloroform with ethanolic potassium hydroxide
(KOH) is
(1) An amide (2) An amide and nitro compound
(3) An ethyl isocyanide (4) An alkyl halide
Sol. Answer (3)

NH2 + CHCl3 OH N=C (Carbylamine reaction)


(Isocyanide)

33. In the reaction,


HCl Boiling H O
 X   2 Y;
CH3CN + 2H Ether

the term Y is
(1) Acetaldehyde (2) Ethanamine (3) Acetone (4) Dimethylamine
Sol. Answer (1)
O
[H] Boiling
CH3CN CH3CH = NH CH3 H
H2O
X Y
34. Amides may be converted into amines by a reaction named after
(1) Hofmann (2) Claisen (3) Perkin (4) Kekule
Sol. Answer (1)
O –
Br2,OH
R – C – NH2 Hoffman
R–NH2
(amide) reaction amines

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35. Diazo-coupling is useful to prepare some
(1) Dyes (2) Vitamins (3) Pesticides (4) Proteins
Sol. Answer (1)
Diazo coupling gives Dyes.

36. Aniline on nitration gives


NH2 NH2 NH2
NO2
(1) (2) (3) (4) All of these
NO2
NO2
Sol. Answer (4)
conc NH2 NH2 NH2
HNO3/
H2SO4 NO2
NH2 + +
NO2 NO2
51% 47% 2%
37. Aniline is reacted with bromine water and the resulting product is treated with an aqueous solution of sodium
nitrite in presence of dilute hydrochloric acid. The compound so formed is converted into a tetrafluoroborate
which is subsequently heated dry. The final product is
(1) p-bromoaniline (2) p-bromofluorobenzene
(3) 1, 3, 5-tribromobenzene (4) 2, 4, 6-tribromofluorobenzene
Sol. Answer (4)
Br Br Br
+ –
NH2 Br2 HONO + – H BF4
Br NH2 Br N2 Cl Br F
H2O
Br Br Br

38. Phenyl isocyanides are prepared by which the following reaction?


(1) Reimer-Tiemann reaction (2) Carbylamine reaction
(3) Rosenmund’s reaction (4) Wurtz reaction
Sol. Answer (2)

NH2 + CHCl3 + OH– N C

This is carbylamine reaction.

CHCl3 /KOH
39. A 
Reduction
 B   C 
Reduction

N– methyl aniline.
Then A is
NH2 NO2 NC

(1) (2) (3) CH3NH2 (4)

Sol. Answer (2)


NO2 NH2 N C
NH – CH3
reduction CHCl3 [H]

OH
(N - methyl aniline)
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252 Amines Solutions of Assignment (Set-2)

40. The final product C, obtained in this reaction


NH2

Ac2O Br2 H2O


A B C
CH3COOH H+

CH3
would be

NH2 COCH3 NH2 NHCOCH3


Br Br Br
COCH3
(1) (2) (3) (4)

CH3 CH3 CH3 CH3

Sol. Answer (3)

O O
NH2 NH–C–CH3 NH–C–CH3 NH2
Br Br
Br2, AlOH H2O
+ Al2O
H+

CH3 CH3 CH3 CH3


(A) (B) (C)

41. Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO3 and conc. H2SO4. In the
mixture, nitric acid acts as a/an
(1) Catalyst (2) Reducing agent (3) Acid (4) Base
Sol. Answer (4)
+ +
HNO3 + H2SO4 H – O – NO2 NO2
(Nitronium
H
ion)
HNO3 is acts as a base.

42. How many isomers of molecular formula C3H9N will liberate N2 gas on treatment with HNO2?
(1) One (2) Three (3) Two (4) Five
Sol. Answer (3)
NH2 HONO
N2
(10)
NH2
HONO
N2
(1°)

NO2
(NH4)2S Br2
43. (A) CH3COOH
(B) .
NO2

The product (B) is


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Solutions of Assignment (Set-2) Amines 253

NH2 NO2 NH2


NO2

(1) (2) (3) (4)


NH2 NH2 Br
Br NH2
Br Br NH2

Sol. Answer (3)

NO2 NH2 NH2


Br
S
(NH4)2 Br21

NO2 AlOH
NO2 NO2

44. The compound which can show tautomerism


(1) CH3CH2 – NO2 (2) CH3 – C – NH2 (3) CH3 – C – CH3 (4) All of these
O O
Sol. Answer (4)

O OH
CH3 – CH – N CH3 – CH = N
O O
CH3 – C – NH2 CH2 = C – NH2
O OH
O OH

CH3 CH3 CH2 CH3

45. In the given reaction

N2Cl

NaNO2/HCl H3PO4
(A) (B) – (C)
OH
NH2

The product (C) is

OH

(1) (2)
NH OH

N=N N=N
(3) (4)
OH HO NH2
Sol. Answer (3)

N2+
HONO H2O
+ Boiling
N=N OH
NH2 NH2 OH

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254 Amines Solutions of Assignment (Set-2)

SECTION - D
Assertion-Reason Type Questions

1. A : Arene diazonium salts are more stable than alkane diazonium salts.

R : Positive charge is dispersed on ring in arene diazonium salts.

Sol. Answer (1)

Correct positive charge is in conjugation with -electrons of benzene ring.

2. A : Aniline does not undergo Friedel Craft's reaction.

R : NH2 group of Aniline is deactivating group for all reactions.

Sol. Answer (3)

In NH2 NH2 is highly ring activating group. (Powerful ortho and para director).

3. A : When R3C–NH2 is oxidised with KMnO4 R3C–NO2 is formed in good yield.


R : KMnO4, always oxidises Amines to Nitro compounds.
Sol. Answer (3 )
KMnO4 oxidise 1° amine to aldehydes and ketones.
KMnO H O /H 
R  CH 2  NH 2   H4
 R  CH  NH  2   R  CHO
2

R R R
+
KMnO4 H2O/H
CH NH2 CH NH CH O
–H2
R H R
2° amine to Tetraalkylhydrazine
R R R
KMnO4
2 NH N N
–H2
R R R

4. A : Lower Aliphatic amines are soluble in water.


R : Lower Aliphatic amines are gases.
Sol. Answer (2)
A : Because of tendency of forming H-bonding in H2O.
R : Fact. but not explanation for A.

5. A : Intermolecular Association is more in Primary amines than 2° & 3° amines.


R : More number of hydrogen atoms are available in Primary amines for hydrogen bonding.
Sol. Answer (1)
H ----- OH R R
+ N – H ----- OH
R– R – N – H ----- OH2 R – N – H ----- OH2
2

H ----- OH2 H ----- OH2 R


I° amine

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Solutions of Assignment (Set-2) Amines 255
6. A : Aniline is not prepared by Gabriel phthalimide synthesis.
R : Due to partial double bond character in haloarene because of resonance.
Sol. Answer (1)

Yes further V.V. less reactantly of Cl towards SN2.

7. A : Phthalimide is less basic than acetamide.


R : Acetamide is more basic than ethyl amine.
Sol. Answer (3)
O
In acid amide lone pair is in conjugation which is not in case of C2H3 – NH2 R C NH2 -pm conjugation.
CH3

8. A : Primary aliphatic amines react with CS2 and HgCl2, give precipitate of HgS.
R : Secondary amine does not give precipitate of HgS in this reaction.
Sol. Answer (2)
– + – S
   HgCl2
R NH H + C S R NH C SH R N C S + HgS + 2HCl
Alkyl isothiocyanate Mustard oil smell.

R S R S
NH + C S N C SH
R R
2° amine N2N dialkyldithiocarbamic acid

9. A : In Hofmann's bromamide degradation amines formed containing one carbon atom less than carbon atoms
present in amide.
R : This reaction occurs through the formation of nitrine intermediate.
Sol. Answer (3)
The reaction takes place high high formation of Alkyl Isocyanate which on hydrolysis yield 1° amine with one C
less.

10. A : Reaction of carboxylic acid with hydrazoic acid in the presence of conc. H2SO4 to form primary amine is
called Schmidt reaction.
R : In this reaction isocyanate intermediate is formed.
Sol. Answer (2)
O
+
H HN3 –N2
Ar COOH Ar C O Ar C NH N N +
H2O –H
Hydrolysis
Ar N C O Ar NH2

11. A : Due to ortho effect basic nature of substitued aniline decreases.


R : It is due to steric hinderance because of solvation of cation.
Sol. Answer (1)
Fact.

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256 Amines Solutions of Assignment (Set-2)

OH OH N2Cl
OH
12. A : is less reactive than in coupling reaction with .
OH
OH

R : In both —OH group activate the same carbon.


OH
Sol. Answer (1)
Fact

13. A : Urethane on reaction with ammonia gives urea.

O
R : Formula of urethane is NH2 C NH OCH2CH3 .

Sol. Answer (3).

A : It is correct as

O O
NH2 C OC2H5 + NH3 NH2 C NH2 + C2H5OH
(Urethane) (Urea)

Here NH2– replaces C2H5O–.

It is nucleophilic substitution.
O
R : It is wrong as Urethane is NH2 – C – O – C2H5 .

N2Cl

14. A : on reaction with HI/CuI form iodobenzene.

R : It is Sandmeyer's reaction.

Sol. Answer (4)


X

CuX/HCl
N2Cl (Sandmeyer's reaction)

X  Cl, for CN

15. A : Pyrrole is less basic than pyridine.


R : Lone pair electron of nitrogen in pyrrole participate in conjugation to gain aromatic character.

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Solutions of Assignment (Set-2) Amines 257
Sol. Answer (1)
H

N
A and R both are correct. In pyrrole , the lone pair is in conjugation with double bond and makes it aromatric.

N
In pyridine , lone pair is available as the does not undergo in resonance.

 Pyridine is stronger base than pyrrole.

NH2
16. A : on reaction with HNO2 gives CH2 OH as major product.

+ +
R: CH2 carbocation is more stable than carbocation.

Sol. Answer (1)

The reaction is known as Demjanov rearrangement.

+
In CH2 s-character is 17% and is highly stable due to sigma resonance.

17. A : 1°, 2° and 3° amines are separated by Hinsberg's method.

R : Hinsberg's reagent is C6H5SO2Cl.

Sol. Answer (2)


Mixture of 1°, 2° & 3° amines
(i) SO2Cl
(ii) KCH
(iii) Distillation

Distillate 3° amine Mother liquor contain


No reaction with +
[ SO2 N R]K
Ph – SO2 – Cl
R
&
N SO2 Ph
R
Filtered

Filtrate Residue
+ R
[R N Ph SO2]K
N SO2 Ph
R
70% H2SO4
70% H2SO4
R NH2
R2 NH
1° amine
2° amine

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258 Amines Solutions of Assignment (Set-2)

18. A : Nitrobenzene on reduction with Zn/NaOH/ gives hydrazobenzene.


R : Nitrobenzene on reduction with Sn/HCl gives aniline.
Sol. Answer (2)

Zn dust/NaOH/
A. Ph  NO2 
 Ph  NH  NH  Ph
Hydrazobenzene

NO2 NH2
Sn/HCI/
R. (Reduction)

19. A : Coupling reaction is used for the identification of aliphatic primary amine.
R : It is called dye test.
Sol. Answer (4)
1° aime can be identified by treating then with CS2 (Hoffman mustard oil reaction)

20. A : Urea is a diamide of carbonic acid.


R : Aqueous solution of urea is neutral.
Sol. Answer (2)

A correct exchange { } exchange


H 2N C NH2
NH2 NH2

  

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