Nitrogen Containing Compounds
Nitrogen Containing Compounds
Nitrogen Containing Compounds
ORGANIC
CHEMISTRY
ENTHUSIAST | LEADER | ACHIEVER
EXERCISE
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(3) Does not affect the litmus
(4) Decolourise the litmus HD0011
AM0002 10. Melting points are normally the highest for
3. Ethanamine can be obtained if the following (1) Tertiary amides (2) Secondary amides
(3) Primary amides (4) Amines
compound is heated with [KOH + Br2]
GC0012
(1) Ethanamide (2) Methanamide
(3) Propionamide (4) All the above 11. Solubility of ethylamine in water is due to
AM0003 (1) Low molecular weight
(2) Ethyl group is present in ethyl alcohol
PO
Na/EtOH
4. CH3CONH2 →
2 5
I A
II → B (3) Formation of H–bonding with water
Reaction II is called (4) Being a derivative of ammonia
(1) Clemmensen GC0013
(2) Stephen
12. Which of the following compound liberates CO2
(3) Mendius
when treated with NaHCO3
(4) Bouveault–Blanc reduction
CA0004 (1) CH3COCH2NH2 (2) CH3NH2
⊕ ⊕
(3) (CH3 )4NOH (4) CH3NH3Cl
5. Tertiary amine is obtained in the reaction :-
CH3 I
(1) Aniline → CH3 I
→
PO0014
CH3 I
(2) Aniline → 13. The product obtained by the alkaline hydrolysis
Sn/HCl
(3) Nitrobenzene → of C2H5—NCO when treated with t–butyl
(4) None of the above magnesiumbromide, the compound obtained will
AM0007 be
(1) t–butylamine (2) n–butylamine
6. C2H5NH2 cannot be prepared by the reduction of (3) Isobutane (4) n–butane
(1) C2H5NO2 (2) CH3CH=NOH AM0015
(3) C2H5NC (4) CH3CN HNO2 a
AM0008
C6H5CHO
b
7. Gabriel reaction for the synthesis of amines, 14. C2H5NH2 NOCl
c
involves the use of C6H5SO2Cl
(1) 1° amide (2) 2° amide d
(3) Imides (4) Aliphatic amide Which product is a Schiff's base :-
AM0009 (1) a (2) b (3) c (4) d
AM0016
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Chemistry : Nitrogen Containing Compound
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15. Acidic nature of amino group is shown by the 21. Blue litmus can be turned to red by the
reaction :- compound :-
(1) R–NH2 + NOCl → RCl + N2 + H2O (1) ROH (2) RNH2
⊕ ⊕
(2) 2RNH2 + 2Na → 2RNH.Na + H2 (3) R N H3 OH (4) R N H3 Cl
(3) R.CH2NH2 + HNO2 → R.CH2OH + N2+ H2O AM0024
⊕ Θ
(4) R.NH2 + HCl → RNH3 C l 22. Which one of the following amine compound
AM0017 gives alcohol with HNO2 ?
16. The reagent used in the conversion of C2H5NH2 (1) N,N–Dimethylaniline (2) Benzylamine
to C2H5Cl would be :- (3) N–methylaniline (4) Aniline
(1) SO2Cl2 (2) SOCl2 AM0026
(3) NOCl (4) All
ANILINE
AM0018
Br2 /CCl4
17. Hydrogen attached to nitrogen is released in the 23. C6H5NH2 → ? The product is :-
reaction :- (1) Only o– bromoaniline
®
(1) RCONH2 + NaNH2 (2) 2, 4, 6–triboromoaniline
(2) RNH2 + Na (3) o–and p–bromoaniline
(3) Both the above (4) Only p–bromoaniline
(4) None of the abvoe AM0028
GC0019
24. Reaction C6H5NH2 + HAuCl4 →
18. If primary amines are treated with ketones the
⊕
product is :- [C6H5NH3]AuCl4 shows ... behaviour of aniline :-
(1) Urea (2) Guanidine (1) Acidic (2) Neutral
(3) Amide (4) Schiff's base (3) Basic (4) Amphoteric
CC0020 GC0031
19. Reactants of reaction – I are :-
25. Aniline on treatment with bromine water yields
CH3CONH2, KOH, Br2
white precipitate of :-
Reactants of reaction–II are
(1) o–Bromoaniline
CH3NH2, CHCl3, KOH
(2) p–Bromonailine
The intermediate species of reaction–I and
reaction–II are respectively (3) 2, 4, 6–Tribromoaniline
CH3
(3) O2N NH2
CH3
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Chemistry : Nitrogen Containing Compound ®
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27. Which of the following amines give N–nitroso 33. Chloroform and ethanolic KOH is used as a
derivative with NaNO2 and HCl ? reagent in the following reaction :-
(1) C2H5NH2 (2) NH2 (a) Hoffmann carbylamine reaction
®
29. Aniline can be obtained by :- (1) o–Bromoacetanilide
(2) N–Bromoacetanilide
(1) Benzoyl chloride and ammonia
(3) p–Bromoacetanilide
(2) Reduction of benzamide (4) m–Bromoacetanilide
(3) Phenol and ammonia in presence of ZnCl2 AH0042
(4) Benzoic anhydride and ammonia 35. Aromatic nitriles (ArCN) are not prepared by
AM0037 reaction
30. Aniline on direct nitration produces :- (1) ArX + KCN
(1) o–Nitroaniline (2) ArN2+ + CuCN
(2) m–Nitroaniline (3) ArCONH2 + P2O5
(3) p–Nitroaniline (4) ArCONH2 + SOCl2
(4) All AM0043
AH0038
NITRO GROUP, CYANIDE & ISOCYANIDE
31. Nitration of acetanilide followed by hydrolysis
36. Aniline in a set of reactions yielded end product D
gives
(1) o–Nitroaniline only NH2
NaNO2 + HCl CuCN
→ A →B
(2) p–Nitroaniline only 0–5ºC
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38. Which of the following compound gives an 41. Reaction of RCN with sodium and alcohol leads
explosive on decarboxylation ? to the formation of :-
(1) 2,4, 6–Trinitrobenzoicacid
(2) 2, 4–Dinitrobenzoicacid (1) RCONH2 (2) RCOO–NH4+
(3) o–Aminobenzoicacid (3) RCH2NH2 (4) R(CH2)3NH2
(4) o–Hydroxybenzoicacid
AM0050
AM0047
39. The gas leaked from a storage tank of the Union SnCl2 /HCl NaNO2 / HCl
42. C6H5NO2 → A
0°C → B;
Carbide plant in Bhopal gas tragedy was:-
(1) Methylisocyanate Benzene from B, is suitably obtained by using :-
(2) Methylamine (1) Ethanol (2) H3PO2
(3) Ammonia (3) Both the above (4) Methanol
(4) Phosgene
AM0051
AM0048
CH3 43. Which reagent is used to get iodo benzene from
reduction
40. CH3–C–NC → ? benzene diazonium hydrogen sulphate
CH3 [C6H5N2HSO4] :
®
CH3 (1) CuBr, ∆ (2) Cu powder + HI
(1) CH3–C–NH2 (3) KI, ∆ (4) None
CH3 AM0052
CH3
44. Which of the following is used as a solvent in the
(2) CH3–C–NH–CH3 Friedel–Crafts reaction ?
CH3 (1) Toluene (2) Nitrobenzene
CH3 (3) Benzene (4) Aniline
(3) CH3–C–NH–CH2CH3 AH0053
CH3
45. In the Sandmeyer's reaction, —N=N—X group
(4) None of diazonium salt is replaced by :-
AM0049
(1) Halide group (2) Nitro group
(3) —OH group (4) —NHNH2 group
AM0055
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Chemistry : Nitrogen Containing Compound ®
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EXERCISE-II (Previous Year Questions) AIPMT/NEET
AIPMT 2006 AIPMT 2009
CH3
®
AIPMT 2007
N–NO2
2. Which one of the following on reduction with
(3)
LiAlH4 yields a secondary amine ?
NHCH3 NHCH3
(1) Methyl isocyanide (2) Acetamide
NO
(3) Methyl cyanide (4) Nitro ethane (4) +
AM0057 NO
AIPMT 2008 AM0059
AIPMT 2010
3. In a reaction of aniline a coloured product C was
5. Which of the following statements about primary
obtained.
amines is 'False' ?
CH3 (1) Alkyl amines are stronger bases than
NH2 NaNO2/HCl N ammonia
CH3
0° to 5°C
B C (2) Alkyl amines are stronger bases than aryl
amines
The structure C would be :
(3) Alkyl amines react with nitrous acid to
CH3 produce alcohols
NH–NH N
CH3 (4) Aryl amines react with nitrous acid to produce
(1)
phenols
CH3 AM0060
(2) N=N N
CH3 6. Acetamide is treated with the following reagents
separately. Which one of these would yield
N=N–CH2–N methyl amine ?
(3)
CH3 (1) PCl5
O¯ NH2
N=N
+
(2) N=N
(3)
NH2
NH2
(4) (3) N=N
®
AM0063
(4) N=N NH2
AIPMT Mains 2012
8. An organic compound C3H9N (A), when treated AM0069
with nitrous acid, gave an alcohol and N2 gas was
evolved. (A) on warming with CHCl3 and caustic 12. Which of the following will be most stable
potash gave (C) which on reduction gave
isopropylmethylamine. Predict the structure of diazonium salt RN+2 X − ?
(A):
(1) CH3–N–CH3 (1) CH3 N+2 X − (2) C6H5 N+2 X −
CH3 (3) CH3CH2 N+2 X − (4) C6H5CH2 N+2 X −
(2) CH3CH2CH2–NH2
CH3 AM0070
(3) CH–NH2
CH3 AIPMT 2015
(4) CH3CH2–NH–CH3 13. The electrolytic reduction of nitrobenzene in
AM0064
strongly acidic medium produces :-
NEET UG 2013
(1) Azoxybenzene (2) Azobenzene
NO2 NO2 (3) Aniline (4) p-Aminophenol
A AM0071
9. In the reaction A is
Br Br RE-AIPMT 2015
⊕N2Cl 14. The following reaction
(1) H+/H2O H
(2) HgSO4/H2SO4 NH2 N
NaOH
(3) Cu2Cl2 + Cl
O
(4) H3PO2 and H2O O
AM0065
is known by the name :
10. Nitrobenzene on reaction with conc.
HNO3/H2SO4 at 80-100°C forms which one of (1) Acetylation reaction
the following products ? (2) Schotten-Baumann reaction
(1) 1, 2, 4-Trinitrobenzene
(3) Friedel–Craft's reaction
(2) 1, 2-Dinitrobenzene
(3) 1, 3-Dinitrobenzene (4) Perkin's reaction
(4) 1, 4-Dinitrobenzene
AH0066 AM0072
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15. Method by which Aniline cannot be prepared is:- NEET(UG) 2017
(1) reduction of nitrobenzene with H2/Pd in 18. Which of the following reactions is appropriate
ethanol for converting acetamide to methanamine ?
(2) potassium salt of phthalimide treated with (1) Hoffmarnn hypobromamide reaction
chlorobenzene followed by hydrolysis with
(2) Stephens reaction
aqueous NaOH solution
(3) Gabriels phthalimide synthesis
(3) hydrolysis of phenylisocyanide with acidic
solution (4) Carbylamine reaction
(4) degradation of benzamide with bromine in AM0078
alkaline solution
AM0073 NEET(UG) 2019
®
16. Which one of the following nitro-compounds COOH strong heating
does not react with nitrous acid ? + NH3
H3C COOH
(1) H C–C–NO
3 2
H3C O
COOH
CH3 (1) (2) NH
CONH2
C
(2) H3C H NO2 O
O
COOH NH2
H2
C (3) (4)
(3) H3C NO2 NH2 NH2
C
H2
AM0107
H2
C
(4) H3C NO2
CH NEET(UG) 2019 (ODISHA)
H3C
20. The amine that reacts with Hinsberg's reagent to
AM0075
give an alkali insoluble product is :-
17. A given nitrogen-containing aromatic compound
(A) reacts with Sn/HCl, followed by HNO2 to (1) CH3–CH–NH–CH–CH3
give an unstable compound (B). (B), on treatment CH3 CH3
(3) (4)
(1) , (2) ,
AM0130
NEET(UG) 2020 (COVID-19)
NH2 COOH COOH OH
22. Reaction of propanamide with ethanolic sodium
hydroxide and bromine will give
®
(3) , (4) ,
(1) Ethylamine (2) Methylamine
(3) Propylamine (4) Aniline
AM0131 AM0134
NEET(UG) 2021 NEET(UG) 2022
26. Given below are two statements :
23. Identify the compound that will react with
Hinsberg's reagent to give a solid which dissolves Statement I :
in alkali : Primary aliphatic amines react with HNO2 to give
CH2 unstable diazonium salts.
(1)
CH3 NO2 Statement II :
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Pre-Medical
27. The product formed from the following reaction 29. The major product (P) formed in the following
®
OH NH2 HNCOCH3
(3)
(3) (4)
O
NH2 Br Br
(4)
AM0138
Re-NEET(UG) 2022
AM0136
30. Match List - I with List - II :
NEET(UG) 2022 (Overseas)
28. Match List-I with List-II :
List - I List - II
List-I List-II
(Reaction) (Product fromed)
(Amines) (pKb values)
(a) N-methylmethanamine (i) 9.30 (a) Gabriel synthesis (i) Benzaldehyde
(c) N-methylaniline (iii) 4.75 (c) Williamson synthesis (iii) Primary amines
(d) Benzenamine (iv) 3.27 (d) Etard reaction (iv) Salicylic acid
Choose the correct answer from the options Choose the correct answer from the options
(1) (a)-(iv), (b)-(iii), (c)-(i), (d)-(ii) (1) (a) - (iii), (b) - (i), (c) - (ii), (d) - (iv)
(2) (a)-(iii), (b)-(iv), (c)-(i), (d)-(ii) (2) (a) - (ii), (b) - (iii), (c) - (i), (d) - (iv)
(3) (a)-(i), (b)-(iv), (c)-(iii), (d)-(ii) (3) (a) - (iv), (b) - (iii), (c) - (i), (d) - (ii)
(4) (a)-(iv), (b)-(ii), (c)-(i), (d)-(iii) (4) (a) - (iii), (b) - (iv), (c) - (ii), (d) - (i)
AM0137 AM0139
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31. The product formed from the following reaction
sequence is
NH2
(i) (CH3CO)2O, pyridine
(ii) LiAlH4
(iii) H2O
H
N CH3
(1)
NH2
(2)
®
OH
NH2
(3)
OH
NH2
(4)
OH
OH
AM0140
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EXERCISE-III (Analytical Questions) Master Your Understanding
NH3 ∆ Br2 + KOH +
1. A → B → C → CH3 CH2 NH2 4. AgCN
C2H5Br H3 O
→ A → HCOOH + B;
A is :- B 3CHCl Re duction
→ A → C
KOH
(1) CH3COOH
(2) CH3CH2CH2COOH A, B, C respectively in the above sequence are
(1) Ethane amine, methane nitrile and diethyl
(3) CH3–CH–COOH
amine
CH3
(2) Carbyl amino ethane, ethane amine and
(4) CH3CH2COOH primary amine
AM0083 (3) Ethyl isocyanide, ethyl amine and methyl
2. The correct set of the products obtained in the isocyanate
®
reduction ( i ) CH MgBr methyl amine
RCN → (A) , RCN 3
( ii ) H2O
→ (B),
AM0086
hydrolysis HNO2
RNC → (C), RNH2 → (D) CO
(i) KOH H3O⊕
The answer is 5. NH A B+C
(ii) C2H5Br
A B C D CO
(1) 2°Amine Methyl ketone 1° Amine Alcohol B and C in the above sequence are
(2) 1°Amine Methyl ketone 1° Amine Alcohol (1) Benzoic acid + aniline
(2) Phthalic acid + ethylamine
(3) 2°Amine Methyl ketone 2° Amine Acid
(3) Phthalic acid + aniline
(4) 1°Amine Methyl ketone 2° Amine Aldehyde
(4) Benzoic acid + ethylamine
AM0084
AM0087
3. The final product C, obtained in this reaction
would be 6. The end–product in the reaction sequence would
NH2 be :
HNO2 PCl5 NH3
H2O Ethyl amine → A → B →C
Ac2O Br2
A B C
CH3COOH H+ (1) Ethyl cyanide
CH3 (2) Ethyl amine
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8. A compound of mol. wt. 180 gm is acetylated to 13. Using Fe/HCl, which one of the following
give a compound of mol. wt. 390. The number reaction is possible [Here φ = C6H5]
(1) φ–NO2→ φ−NH–NH–φ
of amino groups in the compound are :-
(2) φ–NO2 → φ–NH2
(1) 2 (2) 4 (3) φ–NO2 → φ–NHOH
(3) 5 (4) 6 (4) φ–NO2 → φ–N=N–φ
AM0090 AM0096
14. Total structural isomeric amines possible for
9. In the reaction sequence A, B and C are :- molecular formula C4H11N
(1) 7 (2) 8 (3) 9 (4) 6
Sn NaNO2 /HCl H2 O/ ∆
A HCl
→B
0° C →C
→ C6H5OH NC0109
NOCl NaCN H2 / Ni
(1) Benzene, nitrobenzene, aniline 15. C2 H5 NH2 → A → B →C
®
CH3 – CH – NH2
AM0091 (2)
(3) CH3 CH2 – CH = NH
10. Which one of the following tests can be used to (4) H5C2–N–N=O
identify primary amino group in a given organic
CH2–NH2
compound
AM0110
(1) Iodoform test
16. Which of following will not gives only primary
(2) Victor Meyer's test amine
(3) Carbylamine reaction 3( )
NH Alc
(1) C2 H5 X →
(4) Libermann's reaction (2) CH3 − CN ( ) Na Hg
→
C2 H5 OH
PO0092
O
( i ) LiAlH
11. KCN +4H
→→ A
CH3Cl NaNO2 /HCl
→ Ethanol+ ? (3) CH3 – C – NH2
( ii ) H2 O →
4
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Pre-Medical
19. What is decreasing order of H-bonding in water 23. Which of following can be use to distinguish
for alkyl substituted ammonium cation ? primary, secondary and tertiary amine?
⊕ ⊕ ⊕
(1) Carbyl amine reaction
(1) R NH3 > R 2 NH2 > R 3 NH
⊕ ⊕ ⊕
(2) Reaction with Nitrous acid
(2) R 3 NH > R 2 NH2 > R NH3 (3) Reaction with Hinsberg's reagent followed by
⊕ ⊕ ⊕ NaOH
(3) R 2 NH2 > R 3 NH > R NH3
(4) Both 2 & 3
⊕ ⊕ ⊕
(4) R 2 NH2 > R NH3 > R 3 NH PO0118
AM0114 24. Which of following is insoluble in alkali?
20. Which of following reaction is not acylation ? O O
O (1) H5C6–S–N–C2H5 (2) H5C6–S–N–CH3
(1) C2H5NH2 + CH3–C–Cl → O C2H5 OH
O O O
(3) H5C6–S–N–C2H5 (4) All of these
(2) C2H5NH2 + CH3–C–O–C–CH3 →
®
O OH
AM0119
(3) C2H5NH2 + CH3C–OCH3 →
25. These days benzene sulphonyl chloride replaced
O by which compound in Hinsberg test :-
O
(4) C2H5NH2 + CH3–C–OH →
AM0115 (1) CH2–S–Cl
21. Which of following will not give acylation
reaction? O
(1) H5C2 – NH2 (2) H5C2 – NH – C2H5 SO2Cl
CH3
C2H5
(2)
(3) C2H5–N (4) H5C6 – NH2
SO2Cl
C2H5
AM0116 (3)
22. Which of following is not correct match?
O CH3
(1) H5C2NH2 + CH3–C–Cl →
(4) SO3H
O
AM0120
H5C2–NH–C–CH3+HCl
(Acylation)
NH2
O CH3I (excess)
26. A
aq. Na2CO3
(2) H5C2NH2 + H5C6–C–Cl →
What will be "A"
O
NH2 NH2
H5C2–NH–C–C6H5+HCl H3C CH3 CH3
(Benzoylation)
(1) (2)
(3) (H5C2)2 NH + CHCl3 + 3KOH →
H5C2 – NC + 3KCl + 3H2O CH2 CH3
(Carbyl amine reaction)
NH2
(4) H5C2 – NH2 + CH3COOH →
⊕
H5 C2 NH3 CH3 COO – ⊕
(Salt formation or
(3) CH3 (4) Ph − N(CH3 )3 I
Neutralisation)
CH3
AM0117
AM0121
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27. Total number of isomers of molecular formula Room NaNO2
32. A + HBF4 B C
C3H9N which will liberate N2 gas on treatment Temprature Cu,∆
Fe/HCl
with nitrous acid?
A
(1) 2 (2) 3 (3) 4 (4) 1 E H⊕
D
AM0122 What is "E"
28. Which of following is water insoluble and stable
(1) N = N – Ph
at room temperature ?
(1) C6H5N2⊕Cl (2) C6H5N2⊕BF4
(2) NH – N = N – Ph
(3) C6H5N2⊕HSO4 (4) All
AM0123
(3) Ph–N=N NH2
29. Which of following reaction do not displace N2
from benzenediazonium salt? NH2
⊕ − Cu2 Cl2 / HCl
(1) ArN Cl →
2
®
Ph
(4) ArN2⊕ Cl − + HBF4
Room
→
temperature
AM0127
AM0124 33. Diazo coupling reaction can be use to distinguish
30. Which of following group can not be introduced (1) Aniline and Benzyl amine
in the benzene ring by sandmeyer reaction? (2) Ethylamine and N-methyl aniline
(1) –Cl (2) –Br (3) –CN (4) –I (3) Aniline and Phenol
AM0125 (4) All of these
31. Formation of benzene from C6H5N2⊕Cl– by use of AM0128
C2H5OH is example of :- 34. What is correct sequence of reagent to form
(1) Redox reaction 2,4,6-tibromofluorobenzene from Aniline?
(2) Electrophilic substitution reaction (1) NaNO2/HCl (0-5°C), HBF4/∆, Br2/H2O
(3) Nucleophilic substitution reaction
(2) Br2/H2O, NaNO2/HCl (0-5°C), HBF4/∆
(4) Elimination reaction
AM0126 (3) NaNO2/HCl (25°C), HBF4/∆, Br2/H2O
(4) Br2/H2O, NaNO2/HCl (0-5°C), HBF4 (Room
temperature)
AM0129
130