1378 Nitrogen Containing Compounds

2. Compounds containing both amino and COOH

groups are known as
(a) Diamines (b) Unknown
(c) Amino acids (d) Enzymes
3. Which of the following is 1 o amine
(a) Ethylene diamine (b) Dimethyl amine
(c) Trimethyl amine (d) N-methyl aniline
 Alkyl nitrites are the esters of nitrous acid. 4. C3 H9 N represents [AMU 1988]
 Nitroparaffins are used as solvents for oils, fats, (a) Primary amine (b) Secondary amine
resins, esters, rubbers and cellulose etc. nitromethane (c) Tertiary amine (d) All of these
is used as high power fuel in racing automobiles. 5. (CH 3 )2 C.CH 2 . CO .CH 3 is [MP PET/PMT 1988]
 Nitrobenzene is good solvent in friedel crafts |
NH 2
reaction because it dissolves AlCl3
(a) Diacetone (b) Acetoneamine
 All amines have basic properties. The basic (c) Diacetoneamine (d) Aminoacetone
property, that is, the tendency of primary, secondary 6. A secondary amine is [KCET 1992]
and tertiary amines to bind a proton, is due to the (a) An organic compound with two  NH 2 groups
unshared pair of electrons on the nitrogen. When a
(b) A compound with two carbon atoms and an
proton is bound, positive ion is formed and originally
 NH 2 group
electrically neutral amine takes on the charge of the
(c) A compound with an  NH 2 group on the
proton. When ions are formed in this way, they are
called onium ions. The ion formed in case of amines carbon atom in number 2 position
are substituted ammonium ions. The hydronium ion, (d) A compound in which two of the hydrogens of
NH 3 have been replaced by organic groups
H3O+ is also the onium ion, which belongs to the class
of oxonium ions. 7. The structural formula of methyl aminomethane
is
 Some derivatives of ammonia arranged in order [MP PMT 1991]
of deecreasing basicity are (CH3)4N+OH–, (CH3)2NH, (a) (CH 3 )2 CHNH 2 (b) (CH 3 )3 N
CH3NH2, (CH3)3N, NH3, C6H5NH2, C6H5NHCH3,
(c) (CH 3 )2 NH (d) CH 3 NH 2
C6H5NH2, (C6H5)2NH, CH3CONH2.
8. Allyl isocyanide has [IIT 1995]
 In water the basicity follows the order : Primary (a) 9 sigma bonds and 4 pi bonds
< Tertiary < Secondary amine, with reference to (b) 8 sigma bonds and 5 pi bonds
hydronium ion, H3O+. In this case solvation factor (c) 8 sigma bonds, 3 pi bonds and 4 non-bonding
and steric effect alter, to some extent, the order of electrons
basicity because of inductive effect alone. (d) 9 sigma bonds, 3 pi bonds and 2 non-bonding
 In a non-polar solvent such as benzene, using electrons
trichloroacetic acid as the reference acid, the basicity 9. Triaminobenzene is a [BHU 1996]
o o
follows the order Tertiary < Secondary < Primary (a) 2 amine (b) 3 amine
amines. The solvation factor is absent but steric (c) 1 o amine (d) Quarternary salt
effect upsets the inductive effect of alkyl groups. 10. CH 2  CH  CH 2  NH  CH 3 is a [RPET 2000]
 Carylamine test is specific for primary amines. (a) Secondary amine (b) Primary amine
(c) Tertiary amine (d) None of these
11. Leakage of which gas was responsible for the
Bhopal tragedy in 1984 [MP PET 2001]
(a) CH 3  N  C  O (b) CH 3  C  N  S
(c) CHCl 3 (d) C6 H 5 COCl
12. Which of the following is not a nitro-derivative
[DCE 2004]
Introduction of Nitrogen Containing Compounds (a) C6 H5 NO 2 (b) CH 3CH 2ONO
O
1. Cyanide ion is (c) CH 3 CH  N (d) C6 H4 (OH )NO2
|
(a) Nucleophilic (b) Electrophilic CH 3 O
(c) Strongly acidic (d) Non-reactive and
13. Acetonitrile is: [MP PMT 2004]
neutral
(a) C2 H 5 CN (b) CH 3 CN
 Nitrogen Containing Compounds 1379
(c) CH 3COCN (d) C6 H5 CH 2CN 9.
Reduction of nitroalkanes yields
14. In alkyl cyanide alkyl group attached with [BCECE 2005] (a) Acid (b) Alcohol
(a) C of CN group (c) Amine (d) Diazo compounds
(b) N of CN group 10. Acetamide changes into methylamine by
(c) Either C or N of CN group (a) Hofmann bromamide reaction
(d) Both C and N of CN group (b) Hofmann reaction
15. Number of isomeric primary amines obtained from (c) Friedel-Craft's reaction
C4 H11 N are (d) Hinsberg
[DPMT 2005] reaction
(a) 3 (b) 4 11. When methyl iodide is heated with ammonia, the
(c) 5 (d) 6 product obtained is
(a) Methylamine
Preparation of Nitrogen Containing Compounds (b) Dimethylamine
(c) Trimethylamine
(d) A mixture of the above three amines
1. Amides may be converted into amines by reaction
12. Acetanilide can be prepared from aniline and
named after [CPMT 1974; MP PET 1992; CBSE PMT 1999]
which of the following
(a) Perkin (b) Claisen
(a) Ethanol (b) Acetaldehyde
(c) Hoffmann (d) Kolbe
(c) Acetone (d) Acetic anhydride
2. Reaction CH 3 CONH 2   gives
NaOBr
13. Reduction of nitroalkanes in neutral medium (e.g.
[CPMT 1983, 93, 97] Zn / NH 4 Cl ) forms mainly
(a) CH 3 Br (b) CH 4 (a) R  NH (b) R  NHOH
2
(c) CH 3COBr (d) CH 3 NH 2 (c) R  N  N  Cl (d) All of these
3. Acetamide is treated separately with the 14. Nitrosobenzene can be prepared by oxidizing
following reagents. Which would give methyl aniline from
amine (a) H 2 SO 4 (b) H 2 SO 5
[IIT 1983; CPMT 1988, 94; MP PET 1993;
(c) H 2 SO 3 (d) K 2 Cr2 O7
MP PMT 1996; AIIMS 1998]
(a) PCl5 (b) NaOH  Br2 15. The Hinsberg's method is used for
(a) Preparation of primary amines
(c) Sodalime (d) Hot conc. H 2SO 4
(b) Preparation of secondary amines
4. The amine formed from an amide by means of (c) Preparation of tertiary amines
bromine and alkali has
(d) Separation of amine mixtures
(a) Same number of C atoms as that of amide
16. Which one of the following compound gives a
(b) One less C atom than that of amide secondary amine on reduction
(c) One more C atom than that of amide (a) Nitromethane (b) Nitrobenzene
(d) Two more C atoms than that of amide (c) Methyl isocyanide (d) Methyl cyanide
Na  C 2 H 5 OH
5. CH 3CN    X 17. Chloropicrin is manufactured by the reaction
The compound X is [MP PMT 1983; BHU 1984] between Cl2 , NaOH and
(a) CH 3CONH 2 (b) CH 3CH 2 NH 2 (a) Nitromethane (b) Nitroethane
(c) C2 H6 (d) CH 3 NHCH 3 (c) Nitrophenol (d) Nitrostyrene
18. In the reaction
6. Ethylamine can be prepared by the action of
bromine and caustic potash on [CPMT 1994]
O
|| 
(a) Acetamide (b) Propionamide R  C  OH    X 
H 3O
 RCH 2 NH 2 ; 'X' is
[H ]

(c) Formamide (d) Methyl cyanide [MP PMT 1990]

7. Ethylamine can be obtained by the [CPMT 1985] (a) Isonitrile (b) Nitrile
(a) Action of NH 3 on ethyl iodide (c) Nitrite (d) Oxime
(b) Action of NH 3 on ethyl alcohol 19. When ethanol is mixed with ammonia and passed
over alumina the compound formed is[CBSE PMT 1990]
(c) Both (a) and (b)
(a) C2 H5 NH 2 (b) C2 H4
(d) None of the above
8. Aniline is usually purified by (c) C2 H5 OC2 H5 (d) CH 3 OCH 3
[CPMT 1983, 93; JIPMER 1997] 20. Which of the following reactions does not yield an
(a) Steam distillation (b) Simple distillation amine
(c) Vacuum distillation (d) Extraction with a [CPMT 1989, 93]
solvent (a) RX  NH 3 
 1380 Nitrogen Containing Compounds
(b) RCH  NOH  [H ] 

Na 29. Which of the following reactions will not give
C 2 H 5 OH
primary amine

(c) RCN  H 2O 
H
 [CPMT 1999]
(a) CH 3CONH 2   
KOH . Br2
(d) RCONH 2  4 H   
LiAlH 4

21. Identify 'B' in the reaction (b) CH 3CN   

LiAlH 4

Acetamide   A 
P2 O5
 B
4H
[MP PET 1995] (c) CH 3 NC   
LiAlH 4


(a) CH 3 NH 2 (b) CH 3CH 2 NH 2 (d) CH 3CONH 2   

LiAlH 4

(c) CH 3 CN (d) CH 3COONH 4 30. Carbylamine reaction is given by

[BHU 1996; EAMCET 1990]
22. Which of the following gives primary amine on
reduction (a) 1 o amine (b) 3 o amine
[MP PMT 1995] (c) 2 o amine (d) Quarternary salts
O 31. The reaction
||
(a) CH 3  CH 2  N  O C6 H5 NH 2  CHCl 3  3 KOH  C6 H5 NC  3 KCl  2 H 2O
(b) CH 3  CH 2  O  N  O is known as [BHU 1996]

(c) CH 3CH 2 NO3 (a) Carbylamine reaction

(b) Reimer-Tiemann reaction
(d) None of these
(c) Kolbe reaction
23. Which of the following is converted into an
(d) Hofmann's degradation
alcohol on treatment with HNO2 [MP PET 1996; MP PMT 1999] Na  ROH
32. CH 3 CONH 2    Z  H 2 O.
(a) Methyl amine (b) Aniline
(c) Dimethyl amine (d) Triethyl amine What is Z ? [CPMT 1996]

24. Which of the following gives RNC, when reacted (a) CH 3 CH 2 NH 2 (b) CH 3 CH 2 NC
with CHCl 3 and KOH [MP PET 1996] (c) CH 3CH 2CH 3 (d) NH 2CONH 2
(a) RNH 2 (b) R2 NH 33. Which of the following reacts with chloroform
  and a base to form phenyl isocyanide [AFMC 1997]
(c) R3 N (d) R 4 N Cl
(a) Aniline (b) Phenol
25. When aniline reacts with NaNO 2 and dil. HCl at (c) Benzene (d) Nitrobenzene
0 o  5 o C, the product formed is [MP PMT 1996; AIIMS 1996]
34. Aromatic primary amine when treated with cold
(a) Nitroaniline HNO2 gives [Pb. CET 2002; DCE 1999]
(b) Benzene diazonium chloride (a) Benzyl alcohol (b) Nitro benzene
(c) Benzene (c) Benzene (d) Diazonium salt
(d) Trinitroaniline 35. Which of the following compound is the strongest
26. Starting from propanoic acid, the following base
reactions were carried out [BHU 1999]

Propanoic acid 

 X  Y 
SOCl 2
 Z NH 3 Br2  KOH (a) Ammonia (b) Aniline
(c) Methylamine (d) N-methyl aniline
What is the compound Z
36. Nitrobenzene combines with hydrogen in the
(a) CH 3  CH 2  Br
presence of platinum to produce [BHU 1999]
(b) CH 3  CH 2  NH 2 (a) Toluene (b) Benzene
O (c) Aniline (d) Azobenzene
(c) CH 3  CH 2  C 
Br N2
(d) CH 3  CH 2  CH 2  NH 2
27. In the reaction 37.   Product
CuCN

CH 3COOH ( A) (B) 

PCl 5
(C). NH 3 NaBrO

the final product (C) is CH 3

(a) Ammonium acetate (b) Acetamide
(c) Amino methane (d) Ethanal The product is [RPET 2000]

28. In the following reaction, X is NH 2 CN

NaNO 2  HCl
X   Y 
Brominatio n
  Z    Tribromobe nzene
Boiling
C 2 H 5 OH
(a) (b)
[CPMT 1999]
(a) Benzoic acid (b) Salicylic acid
CH 3 CH 3
(c) Phenol (d) Aniline
CN NH 2
 Nitrogen Containing Compounds 1381
[Orissa JEE 2002]
(a) LiAlH 4 (b) Sn/HCl
(c) (d) (c) Na/alcohol (d) H 2 /Ni
47. When aniline is treated with sodium nitrite and
38. Ethyl amine on heating with CS 2 in presence of hydrochloric acid at 0oC, it gives [Orissa JEE 2003]
(a) Phenol and N 2 (b) Diazonium salt
HgCl 2 forms [MP PET 2000]
(c) Hydrazo compound (d) No reaction takes
(a) C 2 H 5 NCS (b) (C 2 H 5 )2 S place
Sn  HCl
(c) (C 2 H 5 )2 CS (d) C 2 H 5 (CS )2 48. CH 3 NO 2   CH 3 X , the ‘X’ contain
[CPMT 2003]
39. Which of the following reacts with NaNO 2  HCl
(a)  NH 2 (b)  COOH
to give phenol [MP PMT 2000]
(c)  CHO (d) (CH 3 CO)2 O
(a) C6 H 5 CH 2 NHCH 3 (b) (CH 3 )2 NH
49. In the series of reaction
(c) CH 3 NH 2 (d) C 6 H 5 NH 2
C 6 H 5 NH 2    X 
NaNO 2 / HCl
 Y  N 2  HCl X and
HNO 2
0  5 C CH 2 O
40. Which of the following reactions give RCONH 2
Y are respectively [EAMCET 2003]
[Roorkee 2000]
(a) C 6 H 5  N  N  C 6 H 5 , C 6 H 5 N 2 Cl 
(a) R  C  N  H 2 O 
HCl

(b) C 6 H 5 N 2 Cl  , C 6 H 5  N  N  C 6 H 5
(b) RCOONH 4 heat

(c) C 6 H 5 N 2 Cl  , C 6 H 5 NO 2
(c) R  COCl  NH 3 
(d) C6 H 5 NO 2 , C6 H 6
(d) (RCO ) 2 O  NH 3 

50. Aromatic nitriles (ArCN) are not prepared by
41. When chlorobenzene is treated with NH 3 in reaction
presence of Cu 2 O in xylene at 570 K. The product [AIIMS 2004]
obtained is (a) ArX + KCN (b) ArN 2  CuCN
[Pb. PMT 2000]
(c) ArCONH 2  P2O5 (d) ArCONH 2  SOCl 2
(a) Benzylamine (b) Diazonium salt
(c) Schiff’s base (d) Aniline 51. An organic amino compound reacts with aqueous
42. Nitrobenzene can be prepared from benzene by nitrous acid at low temperature to produce an oily
using a mixture of conc. HNO 3 and conc. H 2 SO 4 . nitroso amine. The compound is :
In the nitrating mixture, HNO 3 acts as a [BHU 2001] (a) CH 3 NH 2 (b) CH 3CH 2 NH 2
(a) Base (b) Acid (c) CH 3CH 2 NH .CH 2CH 3 (d) (CH 3CH 2 )3
(c) Catalyst (d) Reducing agent 52. Azo-dyes are prepared from :[BHU 2004; Pb. CET 2001]
43. The rate determining step for the preparation of (a) Aniline (b) Salicylic acid
nitrobenzene from benzene is [AIIMS 2001] (c) Benzaldehyde (d) Chlorobenzene
  53. Gabriel's phthalimide synthesis is used for the
(a) Removal of NO 2 (b) Removal of NO 3 preparation of
  [CPMT 1982; DPMT 1983]
(c) Formation of NO 2 (d) Formation of NO 3 (a) Primary aromatic amine (b) Secondary amine
44. In this reaction (c) Primary aliphatic amine (d) Tertiary amine
C6 H 5 NH 2  HCl  NaNO 2  X . Product X is 54. For the preparation of p-nitroiodobenzene from p-
[RPMT 2002; AFMC 2002] nitroaniline, the best method is [Orissa JEE 2005]
(a) Aniline hydrochloride (a) NaNO 2 / HCl followed by KI
(b) Nitro aniline (b) NaNO 2 / HCl followed by CuCN
(c) Benzenediazonium chloride
(c) LiAlH 4 followed by I 2
(d) None of these
45. The diazonium salts are the reaction products in (d) NaBH 4 followed by I 2
presence of excess of mineral acid with nitrous 55. KCN reacts readily to give a cyanide with [J & K 2005]
acid and [MP PET 2002] (a) Ethyl alcohol (b) Ethyl bromide
(a) Primary aliphatic amine (c) Bromobenzene (d) Chlorobenzene
(b) Secondary aromatic amine
(c) Primary aromatic amine
(d) Tertiary aliphatic amine
Properties of Nitrogen Containing Compounds
46. In acid medium nitrobenzene is reduced to aniline
1. Which of the following amine will not react with
as shown in the reaction
nitrous acid to give nitrogen
C6 H 5  NO 2  6[H]  C6 H 5  NH 2  2 H 2 O
(a) CH 3 NH 2 (b) CH 3  CH 2  NH 2
The reducing agent used in this reaction is …….
 1382 Nitrogen Containing Compounds
(c) CH 3  CH  NH 2 (d) (CH 3 )3 N (c) An aldehyde (d) A nitrogen oxide
| 12. Which of the following amines would undergo
CH 3 diazotisation
2. Which of the following compound is expected to (a) Primary aliphatic amines (b) P
be most basic [NCERT 1982] (c) Both (a) and (b) (d) None of these
(a) Aniline (b) Methylamine 13. Reaction of primary amines with aldehyde yields
(c) Hydroxylamine (d) Ethylamine [NCERT 1984; Manipal MEE 1995]
3. Which of the following compounds is an amino
(a) Amides (b) Aldimines
acid
[Manipal MEE 1995]
(c) Nitriles (d) Nitro compounds
O 14. When acetamide is treated with HNO 2 , the gas is
||
(a) CH 3  CH 2  C  O  NH 4 evolved
[CPMT 1993]
O
|| (a) H 2 (b) O 2
(b) CH 3  CH  C  OH
| (c) N 2 (d) CH 4
NH 2
15. Nitrobenzene on nitration gives
O
|| [NCERT 1978; CPMT 1989]
(c) CH 3  CH 2  C  NH 2 (a) o-dinitrobenzene (b) p-dinitrobenzene
O (c) m-dinitrobenzene (d) o- and p-
||
(d) CH 3  CH  C  Cl nitrobenzene
|
NH 2 16. Reduction of alkyl nitrites yields
4. Nitro group in nitrobenzene is a [MNR 1986] (a) Alcohol (b) Base
(a) Ortho director (b) Meta director (c) Amine (d) Acid
(c) Para director (d) Ortho and para 17. When primary amines are treated with HCl, the
director product obtained is
5. The alkyl cyanides are (a) An alcohol (b) A cyanide
(a) Acidic (b) Basic (c) An amide (d) Ammonium salt
(c) Neutral (d) Amphoteric 18. Which one is weakest base [BHU 1982; RPMT 2000]
6. The alkyl cyanides when hydrolysed to the
(a) Ammonia (b) Methylamine
corresponding acid, the gas evolved is
(a) N 2 (b) O 2 (c) Dimethylamine (d) Trimethylamine
19. Chloroform when treated with aniline and
(c) NH 3 (d) CO 2
alcoholic KOH gives [CPMT 1986; EAMCET 1992;
7. Aniline when treated with HNO2 and HCl at 0 o C MP PMT 1997; Pb. PMT 1999]
gives (a) Phenyl cyanide (b) Phenyl isocyanide
[CPMT 1982, 89; RPMT 2000] (c) Chlorobenzene (d) Phenol
(a) Phenol (b) Nitrobenzene 20. Which of following do not react with HNO2
(c) A diazo compound (d) None of these
(a) Primary nitroalkanes (b) Secondary
8. Nitrosobenzene can be isolated from nitrobenzene nitroalkanes
under
(c) Tertiary nitroalkanes(d) All of these
[DPMT 1982]
21. Primary amines can be distinguished from
(a) Metal and acid
secondary and tertiary amines by reacting with[CPMT 1983
(b) Zn dust and NH 4 Cl
(a) Chloroform and alcoholic KOH
(c) Alkaline sodium arsenite (b) Methyl iodide
(d) Cannot be isolated
(c) Chloroform alone
9. Alkyl cyanides when react with Grignard reagent,
(d) Zinc dust
the product on hydrolysis found, is [MP PMT 1980]
22. Which of following is not an usual method for
(a) Aldehyde (b) Ketone
preparation of primary amine
(c) Alcohol (d) Acid
(a) Hofmann's method (b) Curtius reaction
10. The product formed when benzene is nitrated by
fuming nitric acid is [MP PMT 1979]
(c) Schmidt reaction (d) Friedel-Craft's
reaction
(a) m-dinitrobenzene (b) Nitrobenzene
23. A solution of methyl amine
(c) sym-trinitrobenzene (d) None of these
11. Ethyl amine undergoes oxidation in the presence (a) Turns blue litmus red
of KMnO 4 to form [CPMT 1985] (b) Turns red litmus blue
(c) Does not affect red or blue litmus
(a) An acid (b) An alcohol
(d) Bleaches litmus
 Nitrogen Containing Compounds 1383
24. Mark the correct statement (c) Alkyl isothiocyanates (d) Alkyl thiocyanates
[CPMT 1974; DPMT 1983; MP PMT 1994] 37. On heating acetamide in presence of P2O5 , which
(a) Methyl amine is slightly acidic of the following is formed[MP PMT 1992; MP PET 1994;
(b) Methyl amine is less basic than NH 3 Kurukshetra CEE 1998]
(c) Methyl amine is stronger base than NH 3 (a) Ammonium acetate (b) Acetonitrile
(d) Methyl amine forms salts with alkalies (c) NH 3 (d) Methylamines
25. The product of mustard oil reaction is 38. When chloroform reacts with ethyl amine in
(a) Alkyl isothiocyanate (b) Dithio carbonamide presence of alcoholic KOH, the compound formed
is
(c) Dithio ethylacetate (d) Thioether
[CPMT 1983; MP PMT 1993;
26. Which of the following is azo- group
CBSE PMT 1997; BHU 1999; AIEEE 2002]
(a) N  (b)  N  N 
(a) Ethyl cyanide (b) Ethyl isocyanide
(c) NH  (d) CO  NH 
(c) Formic acid (d) An amide
27. 'Oil of mirbane' is
39. When methyl cyanide is hydrolysed in presence of
(a) Aniline (b) Nitrobenzene alkali, the product is [MP PMT 1993; BCECE 2005]
(c) p-nitroaniline (d) p-aminoazobenzene (a) Acetamide (b) Methane
28. The maximum number of  NO 2 groups that can be (c) CO 2  H 2O (d) Acetic acid
introduced by nitration in benzene is usually
40. Hofmann's hypobromite reaction affords a
(a) 4 (b) 2 method of
(c) 3 (d) 6 [MP PMT 1993]
29. Nitrobenzene at room temperature is (a) Preparing a tertiary amine
(a) Gas (b) Liquid (b) Preparing a mixture of amines
(c) Solid (d) Solution (c) Stepping down a series
30. In the explosive amatol, TNT is mixed with[CPMT 1988] (d) Stepping up a series
(a) Ammonium citrate (b) Ammonium nitrate 41. The compound which on reaction with aqueous
(c) Ammonium oxalate (d) Ammonium sulphate nitrous acid on HNO2 at low temperature
31. By reduction of nitrosobenzene which of the produces an oily nitrosoamine is[IIT 1981; CPMT 1989; MP P
following is not obtained Kurukshetra CEE 1998; MP PMT 2001]
(a) Diethylamine (b) Ethylamine
(a) NH2 (b) N=N (c) Aniline (d) Methylamine
42. Identify the product Z in the series
Na  C 2 H 5 OH
CH 3 CN    X   Y 2 2 
 Z
HNO 2 K Cr O
(c) NH.OH (d) NO2 7
H 2 SO 4

[AIIMS 1983; JIPMER 2001]

32. By the presence of a halogen atom in the ring,
basic properties of aniline is (a) CH 3CHO (b) CH 3CONH 2
(a) Increased (b) Decreased (c) CH 3COOH (d) CH 3CH 2 NHOH
(c) Unchanged (d) Doubled 43. The end product of the reactions is
33. In the mustard oil reaction, an amine is treated
C2 H5 NH 2   A 
HNO 2
 B 
PCl 5
 C
H . NH 2
with
(a) Na / C2 H5 OH (b) Sn / HCl [CPMT 1988, 89, 93; DCE 1999; JIPMER 2000]
(a) Ethyl cyanide (b) Ethyl amine
(c) CS 2 (d) K2Cr2O7 / H2SO 4
(c) Methyl amine (d) Acetamide
34. Primary nitro compounds when react with HNO2
44. Primary and secondary amines are distinguished
forms crystalline solids which on treatment with by
NaOH gives [AMU 1988; MP PMT 1996]
(a) Red solution (b) Blue solution (a) Br2 / KOH (b) HClO4
(c) White precipitate (d) Yellow colouration
(c) HNO2 (d) NH 3
35. Secondary nitro compounds when react with
HNO2 forms crystalline solids which one on 45. Which one of the following will give a primary
amine on hydrolysis [BHU 1982]
treatment with NaOH gives
(a) Nitroparaffin (b) Alkyl cyanide
(a) Red solution (b) Blue solution
(c) Oxime (d) Alkyl isocyanide
(c) White precipitate (d) Yellow colouration 46. Methyl amine reacts with HNO2 giving[RPMT 1997]
36. Which of the following possess powerful mustard
(a) CH 3O  N  O (b) CH 3  O  CH 3
smell (and are called mustard oils)
(a) Alkyl isocyanates (b) Alkyl cyanates (c) CH 3 OH (d) (a) and (b) both
 1384 Nitrogen Containing Compounds
47. Nitrobenzene on reduction by zinc and NH 4 Cl (d) Dimethyl amine is less basic than methyl
gives amine
[CPMT 1989, 94; BHU 1996; Pb. PMT 1999] 57. Which of the following is not used as an explosive
(a) Aniline (b) Nitrosobenzene [MP PET 1996]
(c) Hydrazobenzene (d) Phenylhydroxyl (a) Trinitrotoluene (b) Trinitrobenzene
amine (c) Picric acid (d) Nitrobenzene
48. The decreasing order of the basic character of the
58. Primary amines react with nitrous acid to yield
three amines and ammonia is[MP PET/PMT 1988; KCET 1990]
(a) NH 3  CH 3 NH 2  C2 H5 NH 2  C6 H5 NH 2 (a) Insoluble nitrite salts (b) Yellow oily layer
(c) Nitrogen gas (d) Azo dye
(b) C2 H5 NH 2  CH 3 NH 2  NH 3  C6 H5 NH 2
59. Which of the following has the smell of bitter
(c) C6 H5 NH 2  C2 H5 NH 2  CH 3 NH 2  NH 3 almonds
(d) CH 3 NH 2  C2 H 5 NH 2  C6 H 5 NH 2  NH 3 (a) Nitromethane (b) Nitroethane
49. Correct order of increasing basicity is[CBSE PMT 1992] (c) Nitrobenzene (d) Aniline
(a) NH 3  C6 H5 NH 2  (C2 H5 )2 NH  C2 H5 NH 2  (C2 H5 )3 N 60. The reaction of HNO2 with 'A' gives quaternary
(b) C6 H5 NH 2  NH 3  (C2 H5 )3 N  (C2 H5 )2 NH  C2 H5 NH 2 ammonium salt. A is [MP PMT 1997]
(c) C6 H5 NH 2  NH 3  C2 H5 NH 2  (C2 H5 )3 N  (C2 H5 )2 NH (a) Methyl amine (b) Dimethyl amine
(d) C6 H5 NH 2  (C2 H5 )3 N  NH 3  C2 H5 NH 2  (C2 H5 )2 NH (c) Trimethyl amine (d) Aniline
50. Among the following compounds nitrobenzene, 61. Reaction of nitrous acid with aliphatic primary
benzene, aniline and phenol, the strongest basic amine in the cold gives[MP PET/PMT 1998; CBSE PMT 1994]
behaviour in acid medium is exhibited by[KCET 1993] (a) A diazonium salt (b) An alcohol
(a) Phenol (b) Aniline (c) A nitrite (d) A dye
(c) Nitrobenzene (d) Benzene 62. In presence of acid, hydrolysis of methyl cyanide
51. Aniline on treatment with excess of bromine gives
water gives [MP PET/PMT 1998]
[AFMC 1990; MP PMT 1991; RPMT 1997]
(a) Acetic acid (b) Methylamine
(a) Aniline bromide (b) o-bromoaniline
(c) p-bromoaniline (d) 2, 4, 6- (c) Methyl alcohol (d) Formic acid
tribromoaniline 63. The amine which does not react with acetyl
52. Unpleasant smelling carbylamines are formed by chloride is or Which of the following cannot be
heating alkali and chloroform with[KCET 1987, 2000, 01] acetylated
(a) Any amine (b) Any aliphatic amine [MP PET 1999; MP PMT 1999]
(c) Any aromatic amine (d) Any primary amine (a) CH 3 NH 2 (b) (CH 3 )2 NH
53. When an organic compound was treated with (c) (CH 3 )3 N (d) None of these
sodium nitrite and hydrochloric acid in the ice
cold, nitrogen gas was evolved copiously. The 64. The fusion of sodium with amine gives mainly
compound is [KCET 1986] [MP PMT 1999; CPMT 2002]
(a) A nitro compound (a) NaCN (b) NaN 3
(b) A primary amine (c) NaSCN (d) NaNO 2
(c) An aliphatic primary amine
(d) An aromatic primary amine 65. Which of the following is most basic[MP PMT 1999]
54. Aniline reacts with alkyl halide to give [KCET 1984] (a) C6 H5 NH 2 (b) (CH 3 )2 NH
(a) Amino compound (c) (CH 3 )3 N (d) NH 3
(b) Tertiary compound
66. In reaction
(c) Quaternary ammonium compound
(d) Azomethane CH 3 CN  2 H  X 
HCl
 Y ; the term Y is
Boiling H 2 O
Ether
55. Aniline on treatment with conc. HNO 3  conc.
[CBSE PMT 1999]
H 2SO 4 mixture yields [AIIMS 1992]
(a) Acetone (b) Ethylamine
(a) o- and p-nitroanilines (b) m-nitroanilines (c) Acetaldehyde (d) Dimethylamine
(c) A black tarry matter (d) No reaction 67. The following compound can be classified as N-N
56. Which statement is not correct [MP PMT 1995] dimethyl propanamine, N-methyl aniline and
(a) Amines form hydrogen bond aniline
(b) Ethyl amine has higher boiling point than [Bihar MEE 1996]
propane (a) Primary, secondary, tertiary
(c) Methyl amine is more basic than ammonia (b) Primary, tertiary, secondary
(c) Secondary, tertiary, primary
 Nitrogen Containing Compounds 1385
(d) Tertiary, primary, secondary
(e) None of these (c) (d)
68. Which of the following compounds does not react
with NaNO 2 and HCl [KCET 1996]

(a) C6 H5 OH (b) C6 H5 NH 2 76. Which one is less alkaline [CPMT 1997]

(c) (CH 3 )3 CNO 2 (d) (CH 3 )3 CHNO 2 (a) NO 2 NH 2 (b) CH 3 O NH 2

69. In the reduction of nitrobenzene, which of the
following is the intermediate (c) C[CPMT
6 H5
1999]NH 2 (d) All of these
(a) C6 H5 N  O
77. In the diazotisation of aniline with sodium nitrite
(b) C6 H5 NH  NH  C6 H5
and hydrochloric acid, an excess of hydrochloric
(c) C6 H5  N  N  C6 H5 acid is used primarily to [Pb. PMT 1998]
O (a) Suppress the concentration of free aniline
 available for coupling
(d) C6 H 5 N  N  C6 H 5
(b) Suppress hydrolysis of phenol
70. Aniline when treated with conc. HNO3 gives (c) Insure a stoichiometric amount of nitrous acid
[KCET 1996] (d) Neutralize the base liberated
NH2 NH2 NH2
NO2 NO2
78. A primary amine can be converted to an alcohol
(a) (b) by the action of [CET Pune 1998]
(a) Alkali (b) Nitrous acid
NH2 (c) Reducing agent (d) Oxidising agent
O NO2 79. Arrange the following in increasing order of
basicity CH 3 NH 2 , (CH 3 )2 NH , C6 H 5 NH 2 , (CH 3 )3 N [AFMC 1997]
(c) (d) (a) (CH 3 )3 N  (CH 3 )2 NH  CH 3 NH 2  C6 H 5 NH 2
(b) (CH 3 )3 N  (CH 3 )2 NH  CH 3 NH 2  C6 H 5 NH 2
O
(c) C6 H 5 NH 2  (CH 3 )3 N  CH 3 NH 2  (CH 3 )2 NH
71. Which one of the following is not a base[EAMCET 1997]
(a) N 2 H 4 (b) NH 2OH (d) C6 H5 NH 2  (CH 3 )3 N  CH 3 NH 2  (CH 3 )2 NH
(c) (CH 3 )3 N (d) HN 3 80. In the reaction

72. p-Nitrobromobenzene can be converted to p- CH 3 CN  CH 3 MgI  A   B
H 2 O/H

nitroaniline by using NaNH 2 . The reaction

The compound B is [KCET 1999]
proceeds through the intermediate named[Orissa JEE 2005] (a) Acetic acid (b) Acetone
(a) Carbocation (b) Carbanion (c) Acetaldehyde (d) Ethyl alcohol
(c) Benzyne (d) Dianion
81. CH 3 CN is known as acetonitrile because [AMU 1999]
73. If methyl is alkyl group, then which order of
basicity is correct [RPMT 1997] (a) It contains an aceto group
(a) R 2 NH  RNH 2  R 3 N  NH 3 (b) On hydrolysis it gives acetic acid
(b) R 2 NH  R 3 N  RNH 2  NH 3 (c) Both (a) and (b)
(c) RNH 2  NH 3  R 2 NH  R 3 N (d) None of these
82. What is formed, when nitrobenzene is reduced
(d) NH 3  RNH 2  R 2 NH  R 3 N
using zinc and alkali
74. Which of the following has the minimum heat of [BHU 2000; AIIMS 2000; CBSE PMT 2000; MH CET 2003]
dissociation (a) Phenol (b) Aniline
[Roorkee Qualifying 1998]
(c) Nitrosobenzene (d) Hydrazobenzene
(a) (CH 3 )3 N  BF3 
(b) (CH 3 )3 N  B(CH 3 )F2 83. RCOCl  2 Me 2 NH  A  Me 2 NH 2 Cl 
(c) (CH 3 )3 N  B(CH 3 )2 F Here A is [RPET 2000]
(d) (CH 3 )3 N  B(CH 3 )3 Me
(a) RCON (b) RCONH 2
75. The major product (70% to 80%) of the reaction Me
between m-dinitrobenzene with NH 4 HS is (c) RCONHMe (d) (RCO )2 NH
NO2 NH2 [AIIMS 1997] 84. Decreasing order of basicity is [RPET 2000]
(1) CH 3 CONH 2 (2) CH 3 CH 2 NH 2
(a) (b) (3) Ph– CH 2 CONH 2
NO2 NO2
NH2 (a) 1 > 2 > 3 (b) 2 > 1 > 3
NH2

NO2 HS NH2
HS
 1386 Nitrogen Containing Compounds
(c) 3 > 2 > 1 (d) None of these 95. Reduction of methyl isocyanide gives [RPMT 2002]
85. Among the following, the strongest base is (a) Ethylamine (b) Methylamine
[UPSEAT 2000; IIT-JEE (Screening) 2000] (c) Dimethylamine (d) Trimethylamine
(a) C6 H 5 NH 2 (b) p  NO 2 C6 H 4 NH 2 96. Reaction of aniline with benzaldehyde is[RPMT 2002]
(c) m  NO 2  C6 H 4 NH 2 (d) C6 H 5 CH 2 NH 2 (a) Polymerisation (b) Condensation
86. Aniline and methyl amine can be differentiated by (c) Addition (d) Substitution
[DPMT 2000] 97. In the reaction C6 H 5 CHO  C6 H 5 NH 2 
(a) Reaction with chloroform and aqueous C6 H 5 N  HCC 6 H 5  H 2 O, the compound
solution of KOH C6 H 5 N  CHC 6 H 5 is known as
(b) Diazotisation followed by coupling with phenol [RPMT 2000; AIIMS 2002; AMU 2001]
(c) Reaction with HNO 2 (a) Aldol (b) Schiff’s reagent
(d) None of these (c) Schiff’s base (d) Benedict reagent
87. The amine which can react with C6 H5  SO 2  Cl to 98. The unshared pair of electrons on a cyanide ion
form a product insoluble in alkali shall be[AMU 2000] can acts as
(a) Primary amine [Kerala (Med.) 2002]
(b) Secondary amine (a) Isocyanide centre (b) Amido centre
(c) Tertiary amine (c) Cationic centre (d) Nucleophilic centre
(d) Both primary and secondary amines NH 2
88. A mixture of benzene and aniline can be separated
by 99. Electrophilic substitution of with
[KCET (Engg.) 2001]
bromine gives
(a) Hot water (b) dil. HCl
[Kerala (Med.) 2002]
(c) dil. NaOH (d) Alcohol
(a) 1, 4, 6-tribromo aniline
89. Nitrobenzene on further excessive nitration gives
(b) 2, 4, 6-tribromo aniline
[AFMC 2001]
(c) 4-bromo aniline
(a) Trinitrobenzene (b) m-dinitrobenzene
(d) 3-bromo aniline
(c) p-dinitrobenzene (d) All of these
100. Mustard gas is obtained by [MP PET 2002]
90. The compound A with following sequence of
reaction gave benzoic acid (a) The action of dilute acids on mustard seeds
 (b) Treating ethylene with mustard oil
A    B 
NaNO 2 / HCl
 C 
KCN

 benzoic acid. The
H 3O

compound A is [AMU 2001] (c) Treating sulphur chloride with ethylene

(a) Nitrobenzene (b) Aniline (d) None of these
(c) Benzaldehyde (d) Amides 101. Which of the following is capable of forming a
91. Which of the following chemicals are used to zwitter ion
manufacture methyl isocyanate that caused [JIPMER 2002]
“Bhopal Tragedy” (a) C6 H 5  OH (b) C6 H 4 (NH 2 )2
(i) Methylamine (ii) Phosgene
(c) CH 2 OH (d) H 2 N  CH 2  COOH
(iii) Phosphine (iv) |
Dimethylamine CH 2 OH
[AIIMS 2005]
102. Which one of the following reducing agents is
(a) (i) and (iii) (b) (iii) and (iv) likely to be the most effective in bringing about
(c) (i) and (ii) (d) (ii) and (iv) the following change
92. An isocyanide on hydrolysis gives [AMU 2001]
O
(a) An amide ||

(b) A carboxylic acid and ammonia R  C NH 2  RCH 2 NH 2 [AMU 2002]

(c) A N-substituted amide (a) H 2  Ni (b) NaBH 4

(d) A 1o-amine and formic acid
(c) LiAlH 4 (d) Na-alcohol
93. Methyl isocyanide on hydrolysis gives[UPSEAT 2001]
(a) CH 3 NH 2 (b) HCOOH 103. During acetylation of amines what is replaced by
acetyl groups [UPSEAT 2002]
(c) CH 3 COOH (d) Both (a) and (b)
(a) Hydrogen atom attached to nitrogen atom
94. Pure aniline is a [UPSEAT 2001]
(b) One or more hydrogen atoms attached to
(a) Colourless solid carbon atom
(b) Brown coloured solid
(c) One or more hydrogen atoms attached to
(c) Colourless liquid
nitrogen atom
(d) Brown coloured liquid
 Nitrogen Containing Compounds 1387
(d) Hydrogen atoms attached to either carbon The product ‘B’ is [RPMT 2003]
atom or nitrogen atom
104. Hydrolysis of acetonitrile in acidic medium (a) (b)
produces OH
[CPMT 2003; RPMT 2003] O O
(a) CH 3 CH 2 OH (b) CH 3 COOH
(c) NH (d) O
(c) CH 3 NC (d) CH 3 COOCH 3
105. Which has a pyramidal structure [UPSEAT 2003]
112. Identify the product Z in the following reaction
(a) Trimethylamine (b) Methanol
C 6 H 5 NH 2   X 
( AC )2 O
  Y 
Br2 / CCl 4
 Z
HOH
(c) Acetylene (d) Water
106. Ethyl amine on acetylation gives [BHU 2002; BVP 2003] [Kerala (Med.) 2003]

(a) N-ethyl acetamide (a) p-Bromoaniline (b) p -

(b) Acetamide Bromoacetophenone
(c) Methyl acetamide (c) o-Bromoacetophenone (d)o-Bromoacetonilide
(d) None 113. Benzaldehyde condenses with N, N-
107. The refluxing of (CH 3 )2 NCOCH 3 with acid gives dimethylaniline in presence of anhydrous ZnCl 2
[BHU 2002; BVP 2003] to give [Kerala (Med.) 2003]
(a) (CH 3 )2 NH  CH 3 COOH (a) Michler’s ketone (b) Azo dye
(b) (CH 3 )2 NCOOH  CH 4 (c) Malachite green (d) Buffer yellow
(c) 2CH 3 OH  CH 3 CONH 2 114. The correct order of reactivity towards the
electrophilic substitution of the compounds
(d) 2CH 3 NH 2  CH 3 COOH
aniline (I) benzene (II) and nitrobenzene (III) is [CBSE PM
108. p-chloro aniline and anilinium hydrogen chloride
(a) I > II > III (b) III > II > I
can be distinguished by [UPSEAT 2003]
(c) II > III > I (d) I < II > III
(a) Sandmaeyer reaction
115. The final product C, obtained in this reaction
(b) Carbyl amine reaction
NH2
(c) Hinsberg’s reaction
  A 
Ac 2 O
 B 
Br2
 C would be
H 2O
(d) AgNO 3 CH 3 COOH H

[CBSE PMT 2003]

NO2
CH3
Conc. H 2 SO 4
109.   A

NHCOCH3 NH2
Product ‘A’ in above reaction is [RPMT 2003] Br COCH3
NO2 NO2 (a) (b)
SO3H
(a) (b) CH3 CH3
SO3H
NO2 COCH3 NH2
Br Br
(c) (d)
(c) (d) None of these

SO3H CH3 CH3

116. The correct order of increasing basic nature for
110. Product obtained by electrolytic reduction of the bases NH 3 , CH 3 NH 2 and (CH 3 )2 NH is [AIEEE 2003]
nitrobenzene in presence of H 2 SO 4 is [RPMT 2003]
(a) CH 3 NH 2  NH 3  (CH 3 )2 NH
(a) o-amino phenol (b) m-amino phenol
(b) (CH 3 )2 NH  NH 3  CH 3 NH 2
(c) p-amino phenol (d) None of these
(c) NH 3  CH 3 NH 2  (CH 3 )2 NH
O
(d) CH 3 NH 2  (CH 3 )2 NH  NH 3
111.  NH 2 OH  A  B .
PPA
H 3O 
117. Nitrobenzene gives N-phenylhydroxylamine by
 1388 Nitrogen Containing Compounds
[AIIMS 2003] (e) None of these
(a) Sn/HCl (b) H 2 /Pd  C 128. Which one of the following compound is most
(c) Zn/NaOH (d) Zn/NH 4 Cl basic ?
[UPSEAT 2004]
118. Among the following the weakest base is [AIIMS 2003]
H H
(a) C6 H 5 CH 2 NH 2 (b) C6 H 5 CH 2 NHCH 3 | |
N N
(c) O 2 N CH 2 NH 2 (d) CH 3 NH CHO N
| O
119. The correct order of basicity of amines in water is H
: (A) (B) (C)
[Pb. CET 2003] (a) (A) (b) (B)
(a) (CH 3 )2 NH  (CH 3 )3 N  CH 3 NH 2 (c) (C) (d) All are equally basic
(b) CH 3 NH 2  (CH 3 )2 NH  (CH 3 )3 N 129. Which one of the following methods is neither
meant for the synthesis nor for separation of
(c) (CH 3 )3 N  (CH 3 )2 NH  CH 3 NH 2
amines [AIEEE 2005]
(d) (CH 3 )3 N  CH 3 NH 2  (CH 3 )2 NH (a) Hinsberg method (b) Hofmann method
120. Complete the following reaction : (c) Wurtz
[MHCET 2004] reaction (d) Curtius reaction
R NH 2  H2SO 4  130. Aniline in a set of reactions yielded a product D.
NH 2
(a) [R NH 3 ] HSO 4 (b) [R NH 3 ]2 SO 42 
  A 
NaNO 2
 B 
CuCN
 C 
H2
 D
HNO 2

(c) R NH 2 .H2SO 4 (d) No reaction HCl Ni

121. Which of the following compound reacts with The structure of product D would be [CBSE PMT 2005]
(a) C6 H5 CH 2 NH 2
chloroform and a base to form phenyl isocyanide ?[MHCET 2003] (b) C6 H 5 NH CH 2 CH 3
(a) Phenol (b) Aniline (c) C6 H5 NHOH (d) C6 H5 CH 2OH
(c) Benzene (d) Nitro benzene 131. Electrolytic reduction of nitrobenzene in weakly
122. Which one doesn't liberate NH 3 when undergoes acidic medium gives [CBSE PMT 2005]
hydrolysis [Orissa JEE 2005] (a) Aniline (b) Nitrosobenzene
(a) Acetanilide (b) Acetonitrile (c) N-Phenylhydroxylamine (d) p-Hydroxylaniline
(c) Acetamide (d) Phenyl isocyanide 132. Among the following compounds C3 H7 NH 2 ,
123. A nitrogen containing organic compound gave an NH 3 , CH 3 NH 2 , C2 H5 NH 2 and C6 H5 NH 2 , the least
oily liquid on heating with bromine and basic compound is
potassium hydroxide solution. On shaking the (a) C3 H7 NH 2 (b) NH 3
product with acetic anhydride, an antipyretic
(c) CH 3 NH 2 (d) C 6 H 5 NH 2
drug was obtained. The reactions indicate that the
starting compound is [KCET 2004] (e) C2 H5 NH 2
(a) Aniline (b) Benzamide 133.
The reduction of which of the following compound
(c) Acetamide (d) Nitrobenzene would yield secondary amine ?
124. Benzamide on reaction with POCl 3 gives[IIT-JEE 2004] (a) Alkyl nitrite
(a) Aniline (b) Chlorobenzene (b) Carbylamine
(c) Benzyl amine (d) Benzonitrile (c) Primary amine
125. Among the following which one does not act as an (d) Secondary nitro compound
intermediate in Hofmann rearrangement [AIIMS 2005] 134. Azo dye is prepared by the coupling of phenol and
.. :
(a) RNCO (b) RCO N
[Pb. CET 2000]
..
(c) RCO N HBr (d) RNC (a) Diazonium chloride
126. Aniline reacts with which of these to form Schiff (b) o-nitro aniline
base (c) Benzoic acid
[AFMC 2004] (d) Chlorobenzene
(a) Acetic acid (b) Benzaldehyde 
135. C6 H 5 NH 2   X 
NaNO 2 HCl
  Y 
Cu 2 (CN )2

H 2O / H
 Z
(c) Acetone (d) NH 3
Z is identified as : [Pb. PMT 2004]
127. Which of the following does not reduce Tollen’s
reagent (a) C6 H5  NH  CH 3
[Kerala PMT 2004] (b) C6 H5  COOH
(a) CH 3 CHO (b) C6 H5 NHOH (c) C6 H5  CH 2  NH 2
(c) HCOOH (d) C6 H5 NO 2
 Nitrogen Containing Compounds 1389
(d) C6 H5  CH 2  COOH
136. When acetamide reacts with Br2 and caustic soda, Tests for Nitrogen Containing Compounds
then we get : [CPMT 2004]
1. When acetamide reacts with Br2 and caustic soda,
(a) Acetic acid (b) Bromoacetic acid
(c) Methyl amine (d) Ethyl amine then we get
137. In the reaction [DPMT 1983; BHU 1997; Orissa JEE 2002;
CPMT 1971, 78, 79, 81, 85, 2000, 03;
CH 3 CN  2 H  X 
 Y ;
HCl Boiling
Ether H 2O MP PMT 1989; MP PET 1995, 2002]
the term Y is: [BHU 2004] (a) Acetic acid (b) Bromoacetic acid
(a) Acetone (b) Ethyl amine (c) Methyl amine (d) Ethane
(c) Acetaldehyde (d) Dimethyl amine 2. In organic compounds, nitrogen is tested in
138. Reaction of cyclohexanone with dimethylamine in Lassaigne's test as
the presence of catalytic amount of an acid forms (a) NaNH 2 (b) NaCN
a compounds if water during the reaction is (c) NaNO 2 (d) NaNO3
continuously removed. The compound formed is
generally known as [AIEEE 2005] 3. Liebermann's nitroso reaction is used for testing
(a) A Schiff’s base (b) An enamine (a) Primary amines (b) Secondary amines
(c) An imine (d) An amine (c) Tertiary amines (d) All the above
4. A nauseating smell in the carbylamine test for
139. R  NH  COH 
  product
3 POCl
pyridine primary amines is due to the formation of[MP PET 1993]
In the given reaction what will be the product [BHU 2005] (a) Isocyanide (b) Chloroform
 (c) Cyanide (d) DDT
(a) R – N = C = O (b) R  N  C 
5. A positive carbylamine test is given by[IIT-JEE 1999]
(c) R  C  N (d) None of these.
(a) N, N-dimethylaniline
140. Which of the following is secondary pollulant.
(b) 2, 4-dimethylaniline
[BHU 2005]
(a) CO2 (b) N2O (c) N-methyl-o-methylaniline
(c) PAN (d) SO2 (d) p-methylbenzylamine
141. Nitration of aniline also gives m-nitro aniline, in 6. The colour of p-amino azobenzene is [BHU 1997]
strong acidic medium because (a) Orange
[Kerala CET 2005] (b) Congo red
(a) In electrophilic substitution reaction amino (c) Bismark brown (d) Indigo
group is meta directive 7. When primary amine is heated with CS 2 in
(b) Inspite of substituents nitro group always
presence of excess mercuric chloride, it gives
goes to m- position
isothiocyanate. This reaction is called[KCET 1998; CPMT 19
(c) In strong acidic medium, nitration of aniline
is a nucleophic substitution reaction (a) Hofmann bromide reaction
(d) In strong acidic medium aniline present as (b) Hofmann mustard oil reaction
anilinium ion (c) Carbylamine reaction
(e) Strong acid, gives nitrate anion, which attacks (d) Perkin reaction
at m-position
8. Diazo-coupling is useful to prepare some[CPMT 1999]
142. Identify the product in following order
(a) Dyes (b) Proteins
3,4,5-Tribromoaniline    ? [Kerala CET 2005]
(i) diazotizat ion
(ii) H 3 PO 2 (c) Pesticides (d) Vitamins
(a) 3, 4,5 –Tribromobenzene 9. Carbylamine test is used in the detection of [DCE 1999]
(b) 1, 2, 3 – Tribromobenzene (a) Aliphatic 2o amine
(c) 2, 4, 6 – Tribromobenzene
(b) Aromatic 1o amine
(d) 3, 4, 5 – Tribromo nitro benzene
(e) 3, 4, 5 – Tribromo phenol (c) Aliphatic 1o amine
143. The correct order of basicity in amines (d) Both aliphatic and aromatic 1o amines
(i) C4 H5 NH 2 (ii) CH 3 NH 2 10. Which of the following substance does not give
(iii) (CH 3 )2 NH (iv) (CH 3 )3 N iodoform test [

[Kerala CET 2005] (a) C6 H 5 CN (b) RNH 2

(a) (i) < (iv) < (ii) < (iii) (b) (iv) < (iii) < (ii) < (i) (c) CH 3 OH (d) All
(c) (i) < (ii) < (iii) < (iv) (d) (ii) < (iii) < (iv) < (i)
(e) (iv) < (iii) < (ii) < (i)
 1390 Nitrogen Containing Compounds
11. Which one of the following compounds when O O
|| ||
heated with KOH and a primary amine gives
(c) R  C  NH 2 (d) R  C  NHOH
carbylamine test
[Orissa JEE 2005]
3    Intermedia te  
HNO / H SO Sn / HCl
5. 2 4
(a) CHCl 3 (b) CH 3 Cl Heat

(c) CH 3 OH (d) CH 3 CN NH2 [BHU 1995]

NH2

(a) (b)
NH2

NH2 NO2

(c) (d)
NH2
NH2
1. The compound
R1 6. The correct order of basicities of the following
compounds is
N  R3
R2 NH
CH 3  C CH 3  CH 2  NH 2 (CH 3 )2 NH
NH 2
forms nitroso amines when the substituents are 2 3
1
[Roorkee 1999]
O
(a) R1  CH 3 , R 2  R3  H ||
CH 3  C  NH 2 [IIT-JEE (Screening) 2001]
(b) R1  R 2  H, R3  C 2 H 5 4
(c) R1  H, R 2  R3  CH 3 (a) 2  1  3  4 (b) 1  3  2  4
(d) R1  CH 3 , R 2  C 2 H 5 , R3  H (c) 3  1  2  4 (d) 1  2  3  4
2. The action of nitrous acid on ethyl amine gives 7. Which of the following would be most reactive
[DPMT 1982; CPMT 1971, 89, 94;
towards nitration [AMU 2000; UPSEAT 2002]

MP PET 1993, 2001; RPMT 1997; Pb. PMT 1999] (a) Benzene (b) Nitro benzene
(a) Ethane (b) Ammonia (c) Toluene (d) Chloro benzene
(c) Ethyl acohol (d) Nitroethane 8. Aniline reacts with acetaldehyde to form
3. Aniline when diazotized in cold and then treated [MHCET 2004; AFMC 2004]
with dimethyl aniline gives a coloured product. (a) Schiff's base (b) Carbylamine
Its structure would be [CBSE PMT 2004]
(c) Immine (d) None of these
(a) (CH 3 )2 N NN 9. p-chloroaniline and anilinium hydrochloride can
be distinguished by [IIT-JEE 1998]

(b) (CH 3 )2 N NH (a) Sandmeyer reaction (b) NaHCO 3

(c) AgNO 3 (d) Carbylamine test

(c) CH 3 NH NN NO2 X
NH CH 3
10. Sn+HCl

(d) CH 3 NN NH 2
In the above reaction 'X' stands for
[CPMT 1986, 2001; MP PET 1992;
4. Indicate which nitrogen compound amongst the KCET (Engg./Med.) 2000]
following would undergo Hofmann's reaction (i.e. (a) NH 2 (b) SnCl 2
reaction with Br2 and strong KOH) to furnish the (c) Cl (d) NH 4 Cl 
primary amine ( R  NH 2 )
NH 2
[CBSE PMT 1989]
O O 11.  CHCl 3  KOH  ?
|| ||
(a) R  C  NH .CH 3 (b) R  C  O.NH 4 [BHU 2000; Pb. PMT 2000; Kerala 2003]
 Nitrogen Containing Compounds 1391
(a) Phenyl isocyanide (b) Benzyl amine (a) (b)
(c) Benzyl chloride (d) None of these
12. The order of basic strength among the following H
amines in benzene solution is[AIIMS 1991; RPMT 2002] NH 2
(a) CH 3 NH 2  (CH 3 )3 N  (CH 3 )2 NH (c) (d)

(b) (CH 3 )2 NH  CH 3 NH 2  (CH 3 )3 N N

(c) CH 3 NH 2  (CH 3 )2 NH  (CH 3 )3 N H
19. Nitroso amines (R2 N  N  O) are soluble in water. On
(d) (CH 3 )3 N  CH 3 NH 2  (CH 3 )2 NH
heating them with concentrated H 2 SO 4 they give
13. The refluxing of (CH 3 )2 NCOCH 3 with acid gives
secondary amines. The reaction is called[AFMC 1998; AIIMS 1
[KCET 1996] (a) Perkin's reaction
(a) 2CH 3 NH 2  CH 3COOH (b) Fittig's reaction
(c) Sandmeyer's reaction
(b) 2CH 3OH  CH 3COOH
(d) Liebermann's nitroso reaction
(c) (CH 3 )2 NH  CH 3COOH 20. A primary amine is formed an amide by the
(d) (CH 3 )2 NCOOH  CH 4 treatment of bromine and alkali. The primary
amine has : [BHU 2004]
14. Order of basicity of ethyl amines is[MP PMT/PET 1988] (a) 1 carbon atom less than amide
(a) Secondary > Primary > Tertiary (b) 1 carbon atom more than amide
(b) Primary > Secondary > Tertiary (c) 1 hydrogen atom less than amide
(c) Secondary > Tertiary > Primary (d) 1 hydrogen atom more than amide
21. The structural formula of Indigo dye is :[DPMT 2004]
(d) Tertiary > Primary > Secondary
O OH
15. The following reaction is [KCET 1996]
OH
NO2 NO2 NO2
(a)
OH
+KOH (solid) +
 
heat
O
(a) Nucleophilic substitution OH
OH
(b) Electrophilic substitution
(c) Free radical substitution NO 2
(d) None of these (b)
16. RNH 2 reacts with C6 H 5 SO 2 Cl in aqueous KOH to
give a clear solution. On acidification a
NO 2
precipitate is obtained which is due to the
formation of [Roorkee 2000] O H
|| |
H
| C N
(a) R  N   SO 2 C6 H 5 OH  (c) C C
|
H N C
  | ||
(b) R  N SO 2 C6 H 5 K H O
(c) R  NHSO 2C6 H5
(d) N N NH 2
(d) C6 H5 SO 2 NH 2
17. If N and S are present in an organic compound
during Lassaigne test, then both changes into[CPMT 1997]
22. Which of the following is the strongest base ?[AIEEE 2004]
(a) Na2 S and NaCN
(b) NaSCN (a) NH 2 (b) NHCH 3
(c) Na 2 SO 3 and NaCN
CH 3
(d) Na2 S and NaCNO
18. The strongest base among the following is
NH 2 CH 2 NH 2
[AIIMS 2004; BHU 2004] (c) (d)

N
N
 1392 Nitrogen Containing Compounds
23. The following compound on hydrolysis in aqueous 3. Assertion : Methyl isocyanide reacts with
acetone will give CH CH 3 CH 3 ozone to form methyl isocyanate.
3
Reason : Methyl isocyanate was responsible
for Bhopal tragedy.
CH 3O NO 2
4. Assertion : Alkyl cyanide can be prepared by
carbylamine reaction
H Cl CH 3
Reason : Ethyl amine when heated with
chloroform in presence of alcoholic
CH 3 CH 3 CH 3
KOH, cyanide is formed.
5. Assertion : CN  ion is an ambident
CH 3O NO 2
nucleophile.
(K:)
Reason : Nucleophiles are electron rich
H OH CH 3 species.
6. Assertion : Sulphanilic acid exists as dipolar
CH 3 CH 3 CH 3
ion whereas p-aminobenzoic acid
does not.
CH 3O NO 2 Reason : Carboxyl group being more acidic
(L:)
than SO 3 H group can easily
OH H CH 3 transfer a H  to the amino group.
7. Assertion : Nitrating mixture used for carrying
CH 3 CH 3 CH 3 our nitration of benzene consists of
conc. HNO 3  conc. H 2 SO 4 .
CH 3O NO 2 Reason : In presence of H 2 SO 4 , HNO 3 acts
(M:)
as a base and produces NO 2  ions.
H CH 3 OH 8. Assertion : In order to convert R–Cl to pure R–
NH2, Gabriel pthalimide synthesis
(a) Mixture of (K) and (L) (b)Mixture of (K) and (M)
can be used.
(c) Only (M) (d) Only (K) Reason : With proper choice of alkyl halides,
pthalimide synthesis can be used to
prepare 1°, 2° or 3° amines.
9. Assertion : Ammonolysis of alkyl halides
involves the reaction between alkyl
halides and alcoholic ammonia.
Reason : Reaction can be used to prepare
only 2° amines.
10. Assertion : Nitroalkanes, but not nitroarenes
Read the assertion and reason carefully to mark the
can be distilled at normal
correct option out of the options given below :
atmospheric pressure.
(a) If both assertion and reason are true and the
Reason : Nitroalkanes are sparingly soluble
reason is the correct explanation of the assertion.
in water while nitroarenes are
(b) If both assertion and reason are true but reason is
insoluble.
not the correct explanation of the assertion.
(c) If assertion is true but reason is false. 11. Assertion : In Hofmann bromide reaction, the
(d) If the assertion and reason both are false. amine formed has one carbon atom
(e) If assertion is false but reason is true. less than the parent 1° amide.
Reason : N-methyl acetamide undergoes
Hofmann bromamide reaction.
1. Assertion : Benzene diazonium chloride does
12. Assertion : Nitrobenzene does not undergo
not give tests for nitrogen:
Friedel Craft alkylation.
Reason : N 2 gas lose takes place during
Reason : Nitrobenzene is used as solvent in
heating laboratory and industry.
[AIIMS 1999]
13. Assertion : Ammonia is less basic than water.
2. Assertion : Amines are basic in nature.
Reason : Nitrogen is less electronegative
Reason : Presence of lone pair of electron on than oxygen.
nitrogen atom. [AIIMS 1999]
14. Assertion : The reaction between a diazo salt
and an aromatic amine or a phenol,
 Nitrogen Containing Compounds 1393
giving an aminoazo or hydroxyazo
compounds is called coupling 1 a 2 c 3 a 4 d 5 c
reaction.
6 d 7 c 8 d 9 c 10 a
Reason : Condensation of diazonium salt
with phenol is carried out in weakly 11 a 12 b 13 b 14 a 15 b
acidic medium.
15. Assertion : Carbylamine reaction involves the Preparation of Nitrogen Containing Compounds
reaction between 1° amine and
chloroform in basic medium. 1 c 2 d 3 b 4 b 5 b
Reason : In carbylamine reaction,  NH 2
6 b 7 c 8 a 9 c 10 a
group is converted into –NC group.
11 d 12 d 13 b 14 b 15 d
16. Assertion : Me 3 N reacts with BF3 whereas
16 c 17 a 18 b 19 a 20 c
Ph3 N does not.
21 b 22 a 23 a 24 a 25 b
Reason : The electron pair on nitrogen atom
in Ph3 N is delocalised in the 26 b 27 c 28 d 29 c 30 a
benzene ring and is not available to 31 a 32 a 33 a 34 d 35 c
boron in BF3 36 c 37 b 38 a 39 d 40 b,c
17. Assertion : p-Anisidine is weaker base than 41 d 42 b 43 c 44 c 45 c
aniline.
46 b 47 b 48 a 49 c 50 a
Reason : OCH 3 group in anisidine exerts –R
51 c 52 a 53 c 54 a 55 b
effect.
18. Assertion : Lower aldehydes and ketones are
soluble in water but the solubility Properties of Nitrogen Containing Compounds
decreases as the molecular mass
1 d 2 d 3 b 4 b 5 a
increases.
Reason : Distinction between aldehydes and 6 c 7 c 8 d 9 b 10 c
ketones can be made by Tollen’s 11 c 12 b 13 b 14 c 15 c
test. 16 a 17 d 18 a 19 b 20 c
[AIIMS 1999]
21 a 22 d 23 b 24 c 25 a
19. Assertion : Aniline hydrogen sulphate on
26 b 27 b 28 c 29 b 30 b
heating forms a mixture of ortho
and para aminobenzene sulphonic 31 d 32 a 33 c 34 a 35 b
acids. 36 c 37 b 38 b 39 d 40 c
Reason : The sulphonic acid group is electron 41 a 42 c 43 b 44 c 45 d
withdrawing. [AIIMS 1996]
46 d 47 d 48 b 49 d 50 b
20. Assertion : p  O2 N  C6 H 5 COCH 3 is prepared
51 d 52 d 53 c 54 c 55 c
by Friedel Crafts acylation of
nitrobenzene. 56 d 57 d 58 c 59 c 60 c

Reason : Nitrobenzene easily undergoes 61 b 62 a 63 c 64 a 65 b

electrophilic substitution reaction.[AIIMS 66
2005]c 67 e 68 c 69 a 70 c
21. Assertion : Alkyl isocyanides in acidified water 71 d 72 c 73 a 74 b 75 b
give alkyl formamides.
76 a 77 a 78 b 79 c 80 b
Reason : In isocyanides, carbon first acts as a
nuclephile and then as an 81 b 82 d 83 a 84 b 85 d
electrophile. 86 b 87 b 88 b 89 b 90 b
[AIIMS 2005] 91 c 92 d 93 d 94 c 95 c
96 b 97 c 98 c 99 b 100 c
101 d 102 a 103 c 104 b 105 a
106 a 107 a 108 d 109 b 110 c
111 c 112 a 113 c 114 a 115 d
116 c 117 d 118 b 119 a 120 b
121 b 122 d 123 b 124 d 125 d
Introduction of Nitrogen Containing Compounds 126 b 127 d 128 b 129 c 130 d
 1394 Nitrogen Containing Compounds
131 a 132 d 133 b 134 a 135 b
136 c 137 c 138 b 139 b 140 c
141 d 142 b 143 a

Tests for Nitrogen Containing Compounds

1 c 2 b 3 b 4 a 5 b
6 a 7 b 8 a 9 d 10 d
11 a

Critical Thinking Questions

1 c 2 c 3 a 4 c 5 b
6 b 7 b 8 a 9 bc 10 a
11 a 12 b 13 c 14 a 15 a
16 c 17 b 18 c 19 d 20 a
21 c 22 d 23 a
 Nitrogen Containing Compounds 1393
Assertion & Reason CH 3 NH 2  Na 2 CO 3  2 NaBr  2 H 2 O
Methy l amine

NaOH / Br
1 a 2 a 3 b 4 d 5 b 4. (b) CH 3  CO  NH 2  2
 CH 3  NH 2
Hofmann' s bromamide (1c)
6 c 7 a 8 c 9 c 10 b
(2c)
Na  C 2 H 5 OH
11 c 12 b 13 e 14 c 15 a 5. (b) CH 3 C  N  4[H ]    CH 3 CH 2 NH 2
Reduction
16 a 17 d 18 b 19 d 20 d 6. (b) CH 3  CH 2  CO  NH 2  Br2  4 KOH 
Propionami de
21 a
CH 3 CH 2 NH 2  K 2 CO 3  2 KBr  2 H 2 O
7. (c) C 2 H 5 I  NH 3  HI  C 2 H 5  NH 2
C 2 H 5 OH  NH 3  H 2 O  C 2 H 5  NH 2
9. (c) CH 3  CH 2  NO 2  6 [H ]  
Sn / HCl

Nitro ethane

CH 3  CH 2  NH 2  2 H 2 O
Ethy l amine

Introduction of Nitrogen Containing Compounds 11. (d) CH 3 I 

3 NH
 CH 3 NH 2 
3
 (CH 3 )2 NH
CH I
 Methy l amine Dimethy l amine
4. (d) C 3 H 9 N can form all the 3 amines. CH 3 I

 (CH 3 )3 N
CH 3 CH 2 CH 2  NH 2 , CH 3  CH 2  NH  CH 3 Trimety hlamine
o o
1 amine 2 amine NH 2 NH  CO  CH 3
CH 3  N  CH 3 CH 3  CO
O
|
12. (d) + + CH 3 COOH
CH 3 CH 3  CO
o Acetic anhy dride
Acetanilide
3 amine
Aniline
5. (c) (CH 3 ) 2 C  O  H .CH 2  COCH 3  NH 3
 
(CH 3 )2 C CH 2 COCH 3 16. (c) CH 3  N  C  4 [H ]    CH 3  NH  CH 3
Reduction

| o
2 amine
NH 2
diacetonea mine 17. (a) CH 3 NO 2  3Cl2  3 NaOH 

8. (d) Allyl isocyanide. CH 2  CH  CH 2  N  C Nitrometha ne

CCl 3  NO 2  3 NaCl  3 H 2 O.
9. (c) NH 2 (chloropicrin)
NH 2 1o Reductio
18. (b) R  CH 2  NH 2
n [H
1 o amine
]
NH 2 R C  N
Nitrile
1 o amine
Hydrolysis
R  COOH  NH 3
12. (b) CH 3 CH 2  O  N  O is a nitrite derivative, H3O
 acid

hence it is not a nitro derivative.

19. (a) C 2 H 5 OH  NH 3  C 2 H 5 NH 2  H 2 O .
alumina

13. (b) CH 3 CN is called acetonitrile....


H O/H
15. (b) Four 1 o amines are possible 20. (c) R  CN  H 2 O 2 RCOOH  NH 3
CH 3 CH 2 CH 2 CH 2 NH 2 , (CH 3 )2 CHCH 2 NH 2 , It yield amine when reduced as –
CH 3 CH (NH 2 )CH 2 CH 3 , (CH 3 )3 CNH 2 R  CN  H 2  R  CH 2  NH 2
PO
21. (b) CH 3 CONH 2  CH 3 CN 
2 5
 CH 3 CH 2 NH 2
4H
Preparation of Nitrogen Containing Compounds
O
||
1. (c) Hofmann’s bromamide reaction 22. (a) CH 3  CH 2  N  O  3 H 2  CH 3 CH 2 NH 2  2 H 2 O .
CH 3  CO  NH 2  Br2  4 KOH  
H 2O
NO
Acetamide 23. (a) CH 3 NH 2 
2
 CH 3 OH  N 2  H 2 O
CH 3 NH 2  K 2 CO 3  2 KBr  2 H 2 O Methy l amine
Methy l amine 24. (a) R  NH 2  CHCl 3  3 KOH  R  NC  3 KCl  3 HO
1 o  amine
2. (d) CH 3 CONH 2   CH 3 NH 2 .
NaOBr

3. (b) CH 3 CONH 2  Br2  4 NaOH  NH 2 N 2Cl

Acetamide

Aniline Benzene diazonium

chloride
 1394 Nitrogen Containing Compounds

25. (b)
NaNO
2

/ HCl
+ 2 H 2O . ArN 2  CuCN  ArCN  N 2  Cu 
o o
5 C
0
ArCONH 2   ArCN
P2 O5
 H 2O

SOCl 2 ArCONH 2  SOCl 2  ArCN  SO 2  2HCl

26. (b) CH 3 CH 2 COOH 
 CH 3 CH 2 COCl  SO 2  HCl
51. (c) Secondary amines gives oily nitrosomine with
CH 3 CH 2 COCl  NH 3  CH 3 CH 2 CONH 2  HCl
nitrous acid.
CH 3 CH 2 CONH 2  Br2 / NaOH  CH 3 CH 2 NH 2  CO 2
Ethy l amine (CH 3 CH 2 )2 NH  HONO  (CH 3 CH 2 )2 N . NO  H 2 O
oily
PCl 5 NH 3
27. (c) CH 3 COOH  CH 3 COCl  CH 3 CONH 2 52. (a) When aniline is treated with HNO 2 at 0–5°C

 CH 3 NH 2
NaOBr then diazonium salt is formed and by the
coupling of diazonium salt and phenol azo
NH 2 NH 2 N 2 Cl
dyes are prepared.
Br Br Br Br
Br2 NaNO 2
NH 2 N   NCl 
28. (d) 
 
HCl
NaNO 2  HCl
Br Br   
0 5  C
Br Br
  
Boiling Aniline Benzene
C 2 H 5 OH diazonium chloride
Br
29. (c) CH 3  N  C 
4 LiAlH
 CH 3  NH  CH 3 N   NCl  OH
sec. amine

Na  ROH
32. (a) CH 3 CONH 2    CH 3 CH 2 OH  H 2 O +  
coupling
weakly alkaline, OH 

NH 2 N C Phenol

33. (a)  CHCl 3  3 KOH   3 KCl  3 H 2O . HO N N

N
35. (c) Methyl amine is the strongest base. Azo dye

pt / H
36. (c) C6 H 5 NO 2  6 H 
2
 C6 H 5 NH 2  2 H 2 O 54. (a) p-nitrobenzene from p-nitroaniline.
Nitrobenze ne Aniline

38. (a) C2 H5 NH 2  CS 2  HgCl 2  C2 H5 NCS  2 HCl  HgS . NO2 NO2 NO2

NaNO
39. (d) C6 H 5 NH 2 
3
 C6 H 5 N 2 Cl 2
H O
HCl  o 
NaNO 2


KI
HCl , 0  5 C
C6 H5 OH  N 2  HCl
NH2 N2+Cl– I
H 2O
41. (d) 2C6 H 5 Cl  2 NH 3 
 p-
chlorobenz ene in xy lene 570 o K p- nitroiodobenzene
nitroaniline
C6 H 5 NH 2  Cu 2 Cl 2  H 2 O 55. (b) C 2 H 5 Br  KCN    C 2 H 5 CN  KBr
alcohol
(Aniline)

44. (c) C6 H5 NH 2  HCl  NaNO 2  C6 H5 N 2Cl

Sn  HCl
46. (b) C 6 H 5 NO 2  6 H   C 6 H 5  NH 2  2 H 2 O Properties of Nitrogen Containing Compounds
o
NaNO  HCl 0 C
47. (b) C6 H 5 NH 2 2
 C6 H 5 N 2 Cl
1. (d) Tertiary amine does not react with nitrous
48. (a) CH 3 NO 2  6 H 
Sn
 CH 3 NH 2  2 H 2 O acid because in it -H atom is absent.
HCl
2. (d) Due to +ve I.E. of alkyl group, N-atom of
49. (c) C6 H 5 NH 2   C6 H 5 N 2 Cl  
NaNO 2 / HCl

2

HNO amines acquires patrial –ve charge and thus
o o
0 C 5 C (X) H 2O electron pair is easily donated.
C6 H 5 NO 2  N 2  HCl 3. (b) CH 3  C H  COOH
|
(Y)
NH 2
50. (a) Halogen have –I and +M effect by which its
The compounds in which both amino ( NH 2 ) as
electron delocalized in benzene ring by
resonance & due to its –I effect its bonded well as acidic (–COOH) group is present is
with benzene ring and cannot be substitute by called amino acid.
CN  & show the inertness against KCN while 4. (b)   

O  N  O : O  N  O : O  N  O :
other option gives Aromatic nitrile ON O
  

+ +

+
 Nitrogen Containing Compounds 1395
19. (b) + CHCl 3  3 KOH  + 3 KCl  3 H2O

20. (c) Because in tertiary nitroalkanes   H atom is

Presence of  NO 2 group decreases electron absent.
density at o- and p- positions. Hence, 21. (a) Primary amine reacts with CHCl 3 and alc. KOH
incoming electrophile goes to m position.
Therefore it is m-directing group. to form isocyanide while secondary and
tertiary amines do not react.
6. (c) R  C  N  2 H 2 O    R  COOH  NH 3
Hy droly sis

22. (d) Friedel-craft’s reaction is used for the

NH 2 N  NCl preparation of alkyl benzene or acetophenone.
o
It is not a method to prepare amine.
7. (c) + HNO 2  HCl  
0 C
+ 2 H 2O CH NH
Diazotizat ion 23. (b) Red 
3

2
 Blue
(Litmus paper)
Benzene diazonium
Aniline
chloride This litmus paper test shows basic nature of
amine.
9. (b) R  C  N  R  Mg  X  R  C  N  Mg  Br 24. (c) Presence of alkyl group increases electron
Alky lcy anide |
R density on nitrogen atom due to +I effect.
Hydrolysis Thus basic nature increases.
Br 25. (a) Mustard oil reaction
R  CO  R  NH 3  Mg HgCl
Ketone OH CH 3  CH 2  NH 2  CS 2 
2

Ethy l amine
NO 2
CH 3  CH 2  N  C  S  H 2 S
Ethy l isothiocy a nate
10. (c) + 3NHO 3  + 3 H 2O
fuming
NO 2 NO 2 NO 2
sym-trinitro benzene
28. (c)  
Nitration
KMnO 4
11. (c) CH 3  CH 2  NH 2  CH 3  CH  NH NO 2 NO 2
Ethy lamine [O ] Aldimine
1, 3, 5-trinitrobenzene

H O
3
 CH 3  CHO
Acetaldehyde
3- nitro group can be introduced.
HNO
12. (b) Only primary aromatic amines can undergo 34. (a) R  CH 2  NO 2 
2
 R  C  NO 2
||
diazotisation. o
1 nitro
13. (b) R  CH 2  NH 2  O  CH  R  N  OH
aldehy de Nitroloic acid
o
  R  C  NO 2
1 amine NaOH
R  CH 2  N  CH  R  H 2O ||
Aldimine
N  O  Na 
14. (c) CH 3  CO  NH 2  HNO 2  CH 3 COOH  N 2   H 2 O (Blood red)
Acetamide Acetic acid
HNO
35. (b) (R)2 CH  NO 2 
2
(R)2 C  NO 2
|
NO2 NO2 N O
conc.H 2 SO 4
15. (c) + HNO 3     Blue colour.
NaOH

conc. NO2 PO
Nitrobenzen m-dinitrobenzene 37. (b) CH 3 CONH 2  CH 3  C  N  H 2 O .
2 5

e Acetamide Acetonitrile
 NO 2 group is meta directing group. 38. (b) CHCl 3  C2 H5 NH 2  3 KOH 

16. (a) R  O  N  O  6 [H ]   ROH  NH 3  H 2 O
Sn / HCl
C2 H 5 N  C  3 KCl  3 H 2 O
Alky l nitrite Alcohol Ethy l isocy anide

17. (d) CH 3  CH 2  NH 2  HCl  CH 3 CH 2  NH 3 Cl  39. (d) CH 3  C  N  2 H 2 O  CH 3 COOH  NH 3

Ethyl ammonium chloride Methy l cy anide Acetic acid

Amines are basic in nature they react with acid to 40. (c) CH 3 CONH 2  Br2  4 KOH 
form salt. (2c )

CH 3 NH 2  K 2 CO 3  3 KBr  2 H 2 O
18. (a) (CH 3 ) 2 NH  CH 3 NH 2  (CH 3 )3 N  N H 3 (1c)
2 o amine is 1o amine o Ammonia is
(a) (C2 H 5 )2 NH  (aq.) HONO  (C2 H 5 )2 N  N  O  H 2 O
3 amine
most basic least basic 41.
 Diethy l nitrosoami ne
NH 2 N C
Na  EtOH
42. (c) CH 3  C  N 
 CH 3  CH 2  NH 2
Reduction

Aniline Phenyl isocyanide

 NH2

1396 Nitrogen Containing Compounds

HNO 2 K Cr O7 In methyl amine only one electron releasing
  CH 3 CH 2  OH 2 2 
 CH 3 COOH
H 2 SO 4
group is present but in dimethyl amine two
electron releasing groups are present which
HNO PCl
43. (b) C 2 H 5 NH 2 
2
 C 2 H 5 OH 
5
 C 2 H 5 Cl increase the basicity higher in dienethyl
Ethy l amine Ethy l alcohol amine.
NH 57. (d) Nitro compounds are not explosive but stable

3
 C 2 H 5 NH 2
Ethy l amine compound.
44. (c) CH 3 CH 2  NH 2  HNO 2  CH 3 CH 2  OH  N 2  H 2 O 58. (c) CH 3  NH 2  HNO 2  CH 3 OH  N 2  H 2 O
(c) R3 N  HONO  R3 N. HONO
o Alcohol
1 60. called as
(CH 3 CH 2 )2 NH  HNO 2  (CH 3 CH 2 )2 N  N  O  H 2 O Quaternary ammonium salt.
2o Nitroso amine
 NO2 N 2 Cl
45. (d) RN  C  2 H 2 O    RNH 2  HCOOH
Hy droly sis
Alky l Isocy anide o Formic acid
1 amine 4 NO
61. (b) 
2

46. (d) cold
CH 3 NH 2  2 HNO 2  CH 3  O  N  O  N 2  2 H 2 O 4 NO
But R  NH 2 
2
 R  OH  N 2  H 2 O
2CH 3 NH 2  2HNO 2  CH 3  O  CH 3  2 N 2  3 H 2 O cold


NO 2 NO NHOH 62. (a) CH 3 CN 2
H O/H
 CH 3 COOH  NH 3

47. (d) 

2H

2H 63. (c) 3 o amine cannot be Acetylated because
Zn / NH 4 Cl 2 Zn / NH 4 Cl replacable H-atom is absent.
Phenyl hydroxyl 67. (e) Because
amine N-N dimethyl propanimine
50. (b) Because the N atom in aniline has a lone pair CH 3
to donate and also due to +I effect of  NH 2 |
CH 3  N  CH 2  CH 2  CH 3
group. NH 2 3 o amine

Br Br NH  CH 3
NH 2

51. (d) + Bromine water  N-Methyl aniline 

excess Br
o
2 amine
aniline  1 amine. o

52. (d) R  NH 2  CHCl 3  3 NaOH  RN  C  3 NaCl  3 H 2O 68. (c) Replacable H  is absent.
The unpleasant smell is due to the formation of NO 2 NO NHOH
isocyanide.
53. (c) RNH 2  NaNO 2  HCl  R  OH  NaCl  N 2  H 2 O
69. (a)  
Zn / HCl

2H

NH 2 NHCH 3 Nitro benzene Nitro benzene N-phenyl

hydroxylamine
54. (c) + CH 3  Cl  + CH 3Cl . O
NH 2 Because oxidation
of aniline occur in
N (CH 3 )2 absence of making
N  (CH 3 )3
HNO
70. (c) 
3

Cl  O effect.
+ CHCl 3  P - Benzoquinone

NO2 NO2 NO2

Quaternary ammonium salt
NH 2 72. (c)  
NaNH 2

 
NH 3
 Br

55. (c) + HNO 3 / H 2 SO 4 A black mass. Br

3, 4-
NH2
aryne

Nitration of aniline without protecting the 73. (a) R 2 NH  RNH 2  R3 N  NH 3 .

amino group is not possible because HNO 3 is a NH 2
NO2
strong oxidising agent which oxidises aniline.
 
CH 3 75. (b) + NH 4 HS 
56. (d) NH and CH 3  NH 2 . NO 2
CH 3 NO 2
 Nitrogen Containing Compounds 1397
76. (a) Because of presence of electron withdrawing O
||
group - NO 2 . H  Ni
102. (a) R  C  NH 2 2 R  CH 2  NH 2
77. (a) To supress the concentration of the aniline 104. (b) CH 3 CN  2 H 2 O  CH 3 COOH  NH 3
HCl

available for coupling other rise coupling

106. (a) CH 3 CH 2 NH 2  CH 3 COCl CH 3 CH 2 NHCOCH 3  HCl
occurs. N Ethy l acetanilid e
78. (b) R  NH 2  HNO 2  R  OH  N 2  H 2 O . O
alcohol ||
CH 3 CH 3
79. (c) C6 H5 NH 2  (CH 3 )3 N  CH 3 NH 2  (CH 3 )2 NH 107. (a) NH  CH 3 COOH  N  C  CH 3
CH 3 CH 3

H O/H
80. (b) CH 3 CN  CH 3 MgI  (CH 3 ) 2 CNMgI 2 108. (d) Anilinium hydrogen chloride produces
(A)  NH 3 chloride ion which gives white precipitate
OH with AgNO 3 . In fact anilium chloride is a part
CH 3 COCH 3  Mg
(B) I ofNO
aniline. NO 2
2

82. (d) C 6 H 5  NO 2   C 6 H 5 NH  NHC 6 H 5  4 H 2 O

10 [ H ]
Zn / NaOH Hydrazo benzene
Conc. H SO SO 3 H
Me  109. (b) 
2

4

83. (a) RCOCl  2 Me 2 NH  RCON  Me 2  N H 2 Cl  
(A)
Me
Me = Methyl.
86. (b) Phenol react with aniline to give diazonium NO 2 NH-OH NH2
salt by coupling but Methyl amine not react
with phenol. 110. (c) 
[H ]

[H ]

87. (b) C6 H 5 SO 2 Cl is called Hinsberg’s reagent they Conc. H 2 SO 4 H 2 SO 4

react with sec amine to form a product in OH

soluble in alkalies. This reaction used to
Nitrobenzene Phenyl hydroxyl p-amino phenol
separate 1 o , 2 o and 3 o amine from their amine
mixture.
88. (b) A mixture of benzene and aniline can be CH 3
H N
separated by dil. HCl. CH 3
C6 H 5 CH  O 
NO2 NO2 113. (c) CH 3
H N
CH 3
89. (b)  HNO 3  
H 2 SO 4
H 2 O Anyhydron
NO2 s
m- ZnCl 2
90. (b) dinitrobenzene CH 3
N
NaNO  HCl
CH 3
C6 H 5 NH 2 2
 C6 H 5 N 2 Cl   C6 H 5 CN
KCN
C6 H 5 CH  H 2O
o
(A) 0 C (B) (C) H3O CH 3
Aniline N
CH 3
C 6 H 5 COOH
(D) Malachite
green
NH 2 NHCOCH 3 NHCOCH 3 NH 2
91. (c) Methyl isocyanate is industrially prepared by
the action of methyl amine with phosgene. Br  Br
Ac O Br H
HCl 115. (d) 2 
2
 
CH3NH2 + COCl2  [CH3NH – CO – Cl] CH 3 COOH Hy droly sis

 CH3 – N = C = O CH 3 CH 3 CH 3 CH 3
 HCl methyl
92. (d) R  NC  2 Hisocyanate
2 O  RNH 2  HCOOH .
119. (a) Basicity of amines increase with increase in
93. (d) CH 3  NC  2 H 2 O  CH 3 NH 2  HCOOH number of CH 3 groups (or any group which
cause +I effect), due to increase in electron
95. (c) CH 3 NC  4 H   (CH 3 )2 NH .
LiAlH 4
ether density on N atom. As a rule, the basicity of t-
NH2 amine should be more than that of s-amine,
NH2 but actually it is found to be lesser than s-
Br Br amines. This is due to stearic hinderence of
99. (b)  3Br2  
Aqueous
bulkier alkyl groups, which decreases the
availability of lone pair of electron on the N
Br atom of the amino group. Hence the correct
2, 4, 6 tribromo
order of basicity is :
aniline
 1398 Nitrogen Containing Compounds
(CH 3 )2 NH  (CH 3 )3 N  CH 3 NH 2 of lone pair on N Aniline become less basic.
120. (b) Amines are basic in nature, hence form salts The Lone pair of N is delocalized into benzene
with acid. ring by resonance
2 RNH 2  H 2 SO 4  [RNH 3 ]2 SO 42 
121. (b) We know that
C 6 H 5 NH 2  CHCl 3  3 KOH  C 6 H 5 NC  3 KCl  3 H 2 O
Aniline Chloroform pheny l isocy anide

Thus in this reaction phenyl isocyanide is

produced. this is called carbylamine reaction. 133. (b) Carbylamine (or isocyanides) give secondary
122. (d) Isocyanides on hydrolysis forms primary amine on reduction.
amines not ammonia RN  C   R  NH  CH 3
Ni / H 2
Carbylamine
123.(b) C6 H5 CONH 2  Br2  KOH  C6 H5 CONHBr  KBr  H 2O Secondary amine

 KOH
134. (a) Azo dye is prepared by the coupling of phenol
and diazonium chloride.
K2CO3  C6 H5 NH 2  

2 KOH
 C6 H 5 NCO  KBr  H 2O
NH 2 N   NCl 
C6 H5 NH 2  (CH 3 CO)2 O  CH 3 CONHC 6 H5  CH 3 COOH
Acetanilid
NaNO 2  HCl
e   
0 5  C
O (antipyreti
|| c)
C  NH 2 CN OH
Benzene
diazonium chloride
124. (d) 
 POCl 3
 H 2O


Benzonitril +  
coupling
Weakly alkaline Medium
O e Phenol
||
125. (d) (i) RCNH 2 + Br2 + KOH  RCONHBr
+ KBr + H2O OH N N
N
(ii) RCONHBr + KOH  RNCO + KBr + H2O p-
(iii) RNCO + 2KOH  RNH2 + K2CO3 hydroxyazobenzene
RCONH2 + Br2 + 4KOH  RNH2 + 2KBr + K2CO3 135. (b) C6 H 5 NH 2 2
 C6 H 5 N 2 Cl
NaNO / HCl

+2H2O (X )
126. (b) Aniline reacts with benzaldehyde and forms H 2O / H 

 C6 H 5 CN 
 C6 H 5  COOH
Cu 2 (CN )2
Schiff's base (benzal aniline) or anils. (Y ) Benzoic acid ( Z )

C6 H 5  NH 2  O  CHC 6 H 5  C6 H 5 N  CHC 6 H 5
H 2O Thus product Z is identified as C6 H 5  COOH
Benzylidine aniline 136. (c) This is Hofman-bromide reaction. In this
127. (d) CH 3 CONH 2  Br2  4 KOH  
2H O reaction one carbon less amines are formed
2
Acetamide
from amides.
CH 3 NH 2  2 KBr  2 K 2 CO 3
(Methy l amine) CH 3 CONH 2    CH 3 NH 2
Br2 / KOH

N 137. (c) CH 3 CN  2 H  HC  CH

HCl
128. (b) | is most basic Ether
H   CH 3 CHO
Boiling H 2 O
  Acetaldeyde
130. (d) NH 2 N 2 Cl CN
CH 3

NaNO 2 138. (b) N


H 2 / Ni
HCl  

CuCN

DIAZOTISATION
CH 3
A B
139. (b) N-alkyl formamides when dehydrated with
CH 2  NH 2 CH 2 OH POCl3 in presence of pyridine give
isocyanides.
 
HNO 2
140. (c) Pollutants which are formed by reaction
Nitrous acid
amongst the primary pollutants (persist in
NO 2 NH 2 C D the environment in the form they are passed
into it) are called as secondary pollutants.
131. (a)  
Weakly
e.g. peroxyacyl nitrates (PAN) are formed
acidic medium
through reaction between nitrogen oxides
132. (d) C6 H 5 NH 2 is least basic compound due to and hydrocarbons in the presence of sunlight.
resonance by which the Lone pair of nitrogen NH2 NH2 NH2 NH2
takes part in resonance & due to unavailability NO2
+ +

.. +
NO2
+ +
NH2 NH2 NH2 NH2 Aniline NO2
p-nitro m-nitro o-nitro
aniline aniline aniline (2%)
.–.
.–. (51%) (47%)

..
 Nitrogen Containing Compounds 1399
141. (d)  
HNO 3 1. (c) R1  H and R2  R3  CH 3
H 2 SO 4
R1 H
N  R3  N  CH 3
R2 CH 3

Sec. amine reacts with Nitrous acid to form

The reason for this is that, in acidic condition nitroso amine yellow liquid.
protonation of  NH 2 group gives anilinium ion
2. (c) CH 3 CH 2 NH 2  HNO 2  CH 3 CH 2 OH  N 2  H 2 O
( NH 3 ) , which is of deactivating nature and of Ethy l amine Ethy l alcohol

m-directive nature.
NH 2 N 2 Cl
NH2 N2Cl
3. (a) 0 5  C
 NaNO 2  2 HCl   
142. (b) diazotizat
 
ion

NaNO 2  HCl / 0  5 o C
Br Br Br Br 2H 2 O  NaCl
Br Br
3,4,5-
Tribromoaniline (CH 3 )2 N H  Cl  N  N  
HCl

H 3 PO 2 dimethyl aniline

Br Br
Br (CH 3 )2 N NN
1,2,3-
143. (a) Basicity order is Tribromobenzene 4. (c) Hofmann degradation of amide
C4 H5 NH 2  (CH 3 )3 N  CH 3 NH 2  (CH 3 )2 NH R  CoNH 2  Br2  4 KOH 
(CH 3 )3 N is less basic due to steric effect R  NH 2  2 KBr  K 2 CO 3  2 H 2 O
while C4 H5 NH 2 is less basic due to primary amine

resonance.
NO 2 NH 2
Tests for Nitrogen Containing Compounds
5. (b)  
HNO 3 / H 2SO 4
 
Sn / HCl

Nitrobenzene Aniline
1. (c) CH 3 CONH 2  Br2  4 NaOH 
Acetamide
6. (b) The relative basic charecter of 1 o ,2 o and 3 o
CH 3 NH 2  Na 2 CO 3  2 NaBr  2 H 2 O
Methy l amine
amines also depends upon the nature of the
NH 2 alkyl group.
is a type of
R Relative basic strength
CH 3 1 o amine and
CH 3 R2 NH  R  NH 2  R3 N  NH 3
5. (b) hence gives +ve
carbyl test C2 H 5 R2 NH  R  NH 2  NH 3  R3 N
CH 3
CHMe 2 R  NH 2  NH 3  R2 NH  R3 N
CMe 3 NH 3  R  NH 2  R2 NH  R3 N
6. (a) N NH 2
7. (b) The nitrogroup is very firmly linked to the
=NColour
Orange benzene nucleus and does not undergo any
displacement reaction. Nitro group
8. (a) Diazo-coupling is useful to prepare some dyes.
deactivates the benzene nucleus.
N = N-Cl + H NH 2 
NH 2 N=CH–CH3
Benzenediazonium
chloride N=N NH 2 +H2O
8. (a)  CH 3  CHO  
Trace of an acid..

p-amino azo benzene (yellow dye)

Anil or Schiff's
11. (a) CHCl 3 gives carbylamine test. base
9. (bc) (1) With NaHCO 3 

RNH 2  CHCl 3  3 KOH (alc.) 
NH 3 Cl  NH 2
RN C  3 KCl  3 H 2 O
alky l isocy anide
 NaHCO 3  + CO 2  NaCl  H 2 O

Critical Thinking Questions Anilinium hydrochloride is an acid salt and

liberates CO 2 from NaHCO 3 .
 1400 Nitrogen Containing Compounds
But p-chloro aniline is basic not acidic it does 21. (c) The class of Indigo dye is Indigoid or vat dye.
not liberate CO 2 . Indigo dyes are insoluble in water.
NH 3 Cl 
22. (d) Lone pair of N are not taking part in
conjugation whereas in other parts lone pairs
(2) With AgNO 3   AgNO 3 
are taking part in conjugation
NH 3 NO 2  AgCl  (White ppt) H
CH 2  N 2
p-chloro aniline does not contain ionic
chlorine to it does not give white ppt with CH 3 H CH 3
AgNO 3
23. (a) CH 3O NO 2
NO 2 NH 2

10. (a) + 6 [H ]  

Sn / HCl
+ 2 H 2O H Cl CH 3
Nitrobenzen Anilin CH 3 CH 3
H
e e
11. (a) C6 H 5  NH 2  CHCl 3  3 KOH 
C6 H 5 NC  3 KCl  3 H 2O   CH 3O
H 2O
NO 2
Pheny l Isocy anide

 Cl 
(CH 3 )2 NH  CH 3 NH 2  (CH 3 )3 N

(Rearrangeme H2O
–H+
12. (b)
H CH 3
K b  5 .4  10 4 4 .5  10 4 0 .6  10 4
13. (c) (CH 3 )2 NCOCH 3  HCl / H 2 O

(CH 3 )2 NH  CH 3 COOH

nt)
14. (a) Order of basicity of amines
(i) 2 o  1 o  3 o CH 3
CH 3 H
(ii) R2 NH  RNH 2  ArCH 2  NH 2  NH 3  ArNH  R 
ArNH 2  ArNH  Ar
L  
H 2O
CH 3O NO 2
NO 2 NO 2 NO 2 H 
OH
15. (a)  KOH (solid)  
heat
+ H CH 3

OH Assertion and Reason

Because OH  is nucleophile.
16. (c) C 6 H 5 SO 2 Cl  RNH 2  RNHSO 2 C 6 H 5  KOH

RNKSO 2 C6 H 5 1. (a) It is true that benzene diazonium chloride

soluble in KOH does not respond Lassaigne test of nitrogen
17. (b) When sulphur and nitrogen both are present because benzene diazonium chloride losses
in organic compound during Lassaigne's Test, N 2 on Slight heat and thus it can't react with
both changes into "sodium thiocyanate". sodium metal.
(NaSCN) which gives a blood red colouration 2. (a) Amines are basic due to the presence of a lone
with Ferric ion. pair of electrons on nitrogen atom. The lone
3 NaCNS  FeCl 3  Fe (CNS )3  3 NaCl pair can be easily donated.
Ferric sulpho cy anide
(Blood red colour) 3. (b) The reason being that the terminal carbon
atom in isocyanide has electron-deficient
H carbon having a sexlet of electrons and hence
does not have aromaticity by which the
Lone pair of electron of Nitrogen does undergoes addition reactions with ozone.
18. (c) 4. (d) When primary amines are heated with
not delocalised in benzene ring so it will
N chloroform in the presence of alcoholic KOH,
be strong base on other hand rest 3 have
| isocyanides are formed. This reaction is
aromaticity i.e., they follow the huckel
H
rule so the electron pair of Nitrogen known as carbylamine reaction. eg. ethyl
delocalised in ring by resonance & amine gives ethyl isocyanide on treatment
resulting they become less basic. with CHCl 3 and alcoholic KOH.
19. (d) Liebermann’s Nitroso reaction. 
20. (a) CH 3 CONH 2  Br2  4 KOH   C 2 H 5  NH 2  CHCl 3  3 KOH (alc ) 
2H O 2 Ethy l amine Chloroform
(Acetamide)

CH 3 NH 2  2 KBr  2 K 2 CO 3 C2 H 5  N  C  3 KCl  3 H 2 O
(Methy lamine)
 Nitrogen Containing Compounds 1401
5. (b) Nucleophilic species which have more than   
R N  C  E   R N  CE 
 RN  C( Nu )E
Nu
one site of reaction are called ambident
 
nucleophiles. R N  C  H 2 O  RN  CHOH  RNHCHO
:C  N : :C  N : alky lformamide

6. (c) SO 3 H group being more acidic

than CO 2 H group can easily transfer a proton
to the amino group.

7. (a) HNO 3  2 H 2 SO 4 2 HSO 4   NO 2  H 3 O
8. (c) Only primary aliphatic amines can be
prepared by Gabriel phthalimide reaction.
9. (c) Reaction can be used to prepare 1°, 2°, 3°
amines and finally quarternary ammonium
salts.
10. (b) Nitroarene cannot be distilled under normal
atmospheric pressure. This is because either
they decompose or they explode on strong
heating.
11. (c) Only 1° amines undergo Hofmann bromamide
reaction. Since CH 3 CONHCH 3 is a 2° amine
therefore, it does not undergo Hofmann
bromamide reaction.
12. (b) Nitrobenzene does not undergo Friedel Craft
reaction because nitro group deactivate the ring
towards electrophilic substitution and drastic
conditions are needed to carry out the
electrophilic substitution reactions.
13. (e) Ammonia is more basic than water. It is
because nitrogen being less electronegative
than oxygen has a greater tendency to donate
electrons.
14. (c) Condensation of diazonium salt with phenol is
carried out in weakly alkaline medium,
( pH  9 ) . This is due to the fact that in
strongly acid medium the OH of a phenol
remains unionised, and an amine forms a salt.
Phenol exists as phenoxide ion and the latter
is readily substituted by electrophiles than
phenol itself. Thus, in phenol, coupling is
carried out in alkaline medium.
15. (a) RNH 2  CHCl 3  3 KOH (alc)  R N 
 C  3 KCl
 3 H 2O
17. (d) p-Anisidine is a stronger base than aniline.
OCH 3 group in anisidine exerts +R– effect.
18. (b) Solubility of aldehydes and ketones decrease
as the molecular mass increase.
20. (d) The nitro group strongly deactivates the
benzene ring towards electrophilic
substitution.
Nitrobenzene does not undergo Friedel-Craft
acylation reaction.
21. (a) In an isocyanide, first an electrophile and
then a nucleophile add at the carbon to form a
species which usually undergoes further
transformations.