Nitrogen Containing Compound

1. Picric acid is [AIEEE-2002]

COOH COOH OH COOH

NO2 NO2 O2N NO2
(1) (2) (3*) (4)
NO2 OH
NO2 NO2
Sol. It is 2, 4, 6-trinitrophenol.
2. When primary amine reacts with chloroform in ethanolic KOH then the product is [AIEEE 2002]
(1*) an isocyanide (2) an aldehyde (3) a cyanide (4) an alcohol.
Sol. C2H5NH2 + CHCI3 + 3KOH C2H5N C + 3KCl + 3HCI Ethyl isocyanide ,fFky vkblkslk;ukbM
3. The functional group, which is found in amino acid is [AIEEE 2002]
(1) COOH group (2) NH2 group (3) CH3 group (4*) both (1) and (2).
Sol. An amino acid is a bifunctional organic molecule that contains both groups, COOH, as well as an amine
group, NH2.
4. The correct order of increasing basic nature for the bases NH3, CH3NH2 and (CH3)2 NH is [AIEEE 2003]
(1) CH3NH2 < NH3 < (CH3)2NH (2) (CH3)2NH < NH3 < CH3NH2
(3*) NH3 < CH3NH2 < (CH3)2NH (4) CH3NH2 < (CH3)2NH < NH3.
Sol. Except the amines containing tertiary butyl group, all lower aliphatic amines are stronger bases than ammonia
becaues of + I (inductive). The alkyl groups, which are electron releasing groups, increase the electron
density around the nitrogen by increasing the avability of the lone pair of electrons to proton or lewis acids
and making the amine more basic. The observed order in the case of lower members is found more basic.
The observed order in the case of lower members is found to be as secondary > primary > tertiary. This
anomolous behaviour or tertiary amines is due to steric factors i.e., crowding of alkyl groups cover nitrogen
atom from all sides and thus makes it unable for protonation.
Thus the relative strength is in order, (CH3)2 NH > CH3NH2 > NH3.

5. Ethyl isocyanide on hydrolysis in acidic medium generates [AIEEE 2003]

(1*) ethylamine salt and methanoic acid (2) propanoic acid and ammonium salt
(3) ethanoic acid and ammonium salt (4) methylamine salt and ethanoic acid.

Sol. Alkyl isocyanides are hydrolysed by dilute mineral acids to form primary amines.
C2H5N H
C + 2H2O
C2H5NH2 + HCOOH
ethylisocyanide ethylamine methanoic acid

6. The reaction of chloroform with alcoholic KOH and p-toluidine forms [AIEEE-2003]

(1) H3C CN (2) H3C N2Cl

(3) H3C NHCHCl2 (4*) H3C NC

NH2 N= C

Sol. + CHCl3 + 2KOH + 3KCl + 3H2O ; This is carbylamine reaction.

CH3 CH3

7. The ammonia evolved from the treatment of 0.30 g of an organic compound for the estimation of nitrogen was
passed in 100mL of 0.1 M sulphuric acid. The excess of acid required 20 mL of 0.5 M sodium hydroxide
solution for complete neutralization. [AIEEE 2004]
The organic compound is
(1) acetamide (2) benzamide (3*) urea (4) thiourea.
AIEEE_Nitrogenous Compounds -1
 100 0.1 2 20 0.5 1
Sol. Equivalents of NH3 evolved =
1000 1000 100
1 14
Precent of nitrogen in the unknown organic compound 100 46.6
100 0.3
14 2
Percentage of nitrogen in urea (NH2)2CO = 100 = 46.6
60
The compound must be urea.

8. Which of the following is the strongest base? [AIEEE 2004]

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

. .
Sol. Lone pairs of N are not taking part in conjugation where as in other parts lone pairs are taking part in
conjugation.

9. Which one of the following methods is neither meant for the synthesis nor for separation of amines ?
[AIEEE 2005]
(1) Hinsberg method (2) Hofmann method (3*) Wurtz reaction (4) Curtius reaction

Sol. In Wurtz reaction alkyl halide reacts with sodium metal in the presence of dry ether to give alkane.

10. Reaction of cyclohexanone with dimethylamine in the presence of catalytic amount of an acid forms a
compound is generally known as [AIEEE 2005]
(1) a Schiffs base (2*) an enamine (3) an imine (4) an amine

Sol.

11. Fluorobenzene (C6H5F) can be synthesized in the laboratory [AIEEE-2006]

(1*) from aniline by diazotisation followed by heating the diazonium salt with HBF4
(2) by direct fluorination of benzene with F2 gas
(3) by reacting bromobenzene with NaF solution
(4) by heating phenol with HF and KF
+ +
F
NH2 N NCl

N NBF4

NaNO dil. HCl HBF
Sol. 2
4
+ N2+ BF3
O 5 C

12. Which one of the following is the strongest base in aqueous solution? [AIEEE 2007]
(1*) Dimethylamine (2) Methylamine (3) Trimethylamine (4) Aniline
Sol. The increasing order of basicity of the given compounds is
(CH3)2 NH > CH3NH2 > (CH3)3 N > C6H5NH2
Due to the +I effect of alkyl groups the electron density on nitrogen increases and thus the abailability of the
lone pair of electrons to proton increases and hence the basicity of amines also increases. So aliphatic
amines are more basic than aniline.
In case of tertiary amine (CH3)3 N, the covering of alkyl groups over nitrogen atom from all sides makes the
approach and bonding by a proton relativly difficult, hence the basicity decreases. Electron withdrawing
(C6H5) groups decreases electron density on nitrogen atom and thereby decreasing basicity.
13. In the chemical reaction, [AIEEE-2007, 3/120]
CH3CH2NH2 + CHCl3 + 3 KOH (A) + (B) + 3H2O, the compounds (A) and (B) are respectively :
(1) C2H5CN and 3KCl (2) CH3CH2CONH2 and 3KCl
(3) C2H5NC and K2CO3 (4*) C2H5NC and 3KCl

AIEEE_Nitrogenous Compounds -2
Sol. C = 3KCl + 3H O
CH3CH2 NH2 + CHCl3 + 3KOH C2H5 N 2
This is carbylamine reaction.
Correct choice (4)

14. Presence of a nitro group in a benzene ring [AIEEE-2007, 3/120]

(1) activates the ring towards electrophilic substitution
(2) renders the ring basic
(3) deactivates the ring towards nucleophilic substitution.
(4*) deactivates the ring towards electrophilic substitution.
Sol. NO2 group in benzene ring shows and R effect, which deactivates the ring towards electrophilic
substitution but activates it towards nucleophilic substitution.
Correct choice (4)

15. The electrophile, E . attacks the benzene ring to generate the intermediate -complex. Of the following,
which s-complex is of lowest energy ? [AIEEE-2008, 3/105]

NO2
NO2 NO2
H
H
+ E +
(1*) (2) + E (3) + (4)
H
E H E

16. In the chemical reactions : [AIEEE-2010, 4/144]

NH2

NaNO 2 HBF4
A B
HCl, 278 K
the compounds A and B respectively are
(1) nitrobenzene and fluorobenzene (2) phenol and benzene
(3*) benzene diazonium chloride and fluorobenzene (4) nitrobenzene and chlorobenzene

Sol. NaNO HCl HBF

4
2


278 K

AIEEE_Nitrogenous Compounds -3