CHAPTERWISE QUESTION

ORGANIC COMPOUNDS CONTAINING NITROGEN Time:1½hours

XII Mark: 35
SET A

Section A
1 Nitrogen atom of amino group is ………. hybridised. 1
a) sp b) sp2 c) sp3 d) sp3d
2 Which of the following does not react with Hinsberg reagent? 1
a) C2H5NH2 b) (CH3)2NH c) (CH3)3N d) CH3CH(NH2)CH3
3 Which of the following reagents would not be a good choice for reducing an 1
aryl nitro compound to an amine?
a) H2(excess)/Pt b) LiAlH4 in ether c) Fe and HCl d) Sn and HCl
4 Name the product(s) formed during the reaction of primary aliphatic amines 1
with nitrous acid at room temperature?
a) RN2+Cl- b) ROH c) Both (a) and (b) d) none of these
5 The most convenient method to prepare primary amine containing one carbon 1
atom less is
a) Gabriel phthalimide synthesis b) Reductive amination of aldehydes
c) Hofmann bromamide reaction d) Reduction of isonitriles
6 Which test can tell the difference between p-chloroaniline and anilinium 1
hydrochloride?
a) Sandmeyer reaction b) Carbylamine test c) AgNO3 d) NaHCO3
Assertion Reason Questions
In the following questions a statement of assertion followed by a statement of
reason is given. Choose the correct answer out of the following choices.
a) Both assertion and reason are true and reason is the correct explanation of
assertion.
b) Both assertion and reason are true but reason is not the correct explanation
of assertion.
c) Assertion is true but reason is false.
d) Assertion is false and reason is true.
7 Assertion : Acetanilide is less basic than aniline. 1
Reason : Acetylation of aniline results in decrease of electron density on
nitrogen
8 Assertion : In strongly acidic solutions, aniline becomes more reactive 1
towards electrophilic reagents.
Reason : The amino group being completely protonated in strongly acidic
solution, the lone pair of electrons on the nitrogen is no longer
available for resonance.
 Section B
9 Why is NH2 group of aniline acetylated before carrying out nitration? 2
10 Electrophilic substitution in case of aromatic amines takes place more readily 2
than benzene. Explain
OR
Out of Butan– 1– ol and butan-1 amine, which will be more soluble in water
and why?
11 Write the IUPAC name of the following compounds and classify them into 2
primary, secondary, and tertiary amines?
i)(CH3)2CHNH2 ii)CH3(CH2)2NH2
Section C
12 Arrange the following in increasing order of their basic strength: 3
i) C2H5NH2, C6H5NH2, NH3, C6H5CH2NH2 and (C2H5)2NH
ii) C2H5NH2, (C2H5)2NH, (C2H5)3N, C6H5NH2
iii) CH3NH2, (CH3)2NH, (CH3)3N, C6H5NH2, C6H5CH2NH2.
13 Give the structures of A, B, C in the following reactions. 3
i) C6H5N2+Cl- CuCN A H2O/H+ B NH3 C
∆
ii) C6H5NO2 Sn + HCl A NaNO2+HCl B H2O/H+ C
273K ∆
14 What happens when 3
a) N-ethyl ethanamine reacts with benzene sulphonyl chloride?
b) benzyl chloride is treated with ammonia followed by the reaction with
chloromethane?
c) aniline reacts with chloroform in the presence of alcoholic potassium
hydroxide?
15 How will you convert 3
i) ethanamine into methanamine
ii) ethanoic acid into propanoic acid
iii) methanamine into ethanamine
OR
How will you convert
i) Benzyl chloride to 2 phenylethanamine
ii) Benzene to Aniline
iii) Aniline to p - bromoaniline
Section D
16 Read the following passage and answer the questions given below. 4
A student selected an amide ‘A’ for producing 10 amine ‘B’ (molar mass 59 g
mol-1)by using Br2/KOH ‘A’ could also be produced from isobutyric acid.
 He was also able to prepare another 10 amine ‘C’ from ‘A’ by using reagent Y.
The molar mass of ‘C’ was determined to be 73 g mol-1.
i) What can be the structure of 10 amine ‘B’?
ii) What is the molar mass of the amide ‘A’ selected by the student?
iii) What is the reagent Y used?
iv)Treatment of B with NaNO2/HCl gives a colourless gas. Name the gas
released
OR
What do we call the reaction involved in the formation of 10amine B?
Section E
17 Give plausible explanation for each of the following: 5
i) Why are amines less acidic than alcohols of comparable molecular masses?
ii) Why do primary amines have higher boiling point than tertiary amines?
iii) Why are aliphatic amines stronger bases than aromatic amines?
iv) pKb of aniline is more than that of methylamine.
v) Aniline does not undergo Friedel-Crafts reaction.
OR
a) How will you convert the following:
i) Nitrobenzene into aniline
ii) Ethanoic acid into methanamine
iii) Aniline into N-phenylethanamide. (Write the chemical equations involved)
b) Write the structures of main products when aniline reacts with the following
reagents:
i) Br2 water ii) HCl iii) (CH3CO)2O/pyridine
 CHAPTERWISE QUESTION
ORGANIC COMPOUNDS CONTAINING NITROGEN
XII Time: 1½ hours
Mark: 35
SET B

Section A
1 When a primary amine reacts with chloroform in ethanolic KOH, then the 1
product is
a) isocyanide b) aldehyde c) cyanide d) alcohol
2 By reacting with which of the following, primary amines can be separated from 1
secondary and tertiary amines?
a) Chloroform alone b) Methyl iodide
c) Chloroform and alcoholic KOH d) Zinc dust
3 Among the following, the strongest base in aqueous medium is 1
a)CH3NH2 b)(CH3)2NH c)(CH3)3N d)C6H5NH2
4 Which of the following statements concerning methylamine is correct? 1
a) Methylamine is stronger base than NH3
b) Methylamine is less basic than NH3
c) Methylamine is slightly acidic
d) Methylamine forms salts with alkali
5 Which of the following compound will not undergo azo coupling reaction with 1
benzene diazonium chloride?
a)Aniline b)Phenol c)Anisole d)Nitrobenzene
6 Which of the following amines are insoluble in water? 1
a) Methanamine b) Ethanamine c) Propanamine d) Benzenamine
Assertion Reason Questions
In the following questions a statement of assertion followed by a statement of
reason is given. Choose the correct answer out of the following choices.
a) Both assertion and reason are true and reason is the correct explanation of
assertion.
b) Both assertion and reason are true but reason is not the correct explanation
of assertion.
c) Assertion is true but reason is false.
d) Assertion is false and reason is true.
7 Assertion : Hoffmann’s bromamide reaction is given by primary amines. 1
Reason : Primary amines are more basic than secondary amines.
8 Assertion : Aromatic primary amine cannot be prepared by Gabriel phthalimide 1
synthesis.
 Reason : Aryl halides do not undergo electrophilic substitution with anion
formed by phthalimide.
Section B
9 What is the role of pyridine in the acylation reaction of amines? 2
10 Why the hydrogen atoms of the methyl group in o- and p- nitrotoluenes are 2
acidic in nature, while those of toluene are not?
OR
Why are amines less acidic than alcohols of comparable molecular masses?
11 Ammonolysis of alkyl halides is not a good method to prepare pure primary 2
amines?
Section C
12 a) Complete the following acid-base reactions and name the products: 3
i) CH3CH2CH2NH2 + HCl →
ii) (C2H5)3N + HCl →
b) Write chemical reaction of aniline with benzoyl chloride and write the name
of the product obtained.
13 Describe a method for the identification of primary, secondary and tertiary 3
amines. Also write chemical equations of the reaction involved.
14 Give reasons for the following. 3
i) Aniline does not undergo Friedel-Crafts reaction.
ii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
iii) Primary amines have higher boiling point than tertiary amines.
15 Write the reactions involved in the following: 3
i) Hofmann bromamides degradation reaction
ii) Diazotisation
iii) Gabriel phthalimide synthesis
OR
Give the structures of A, B and C in the following reactions.
Fe / HCI NaNO2 + HCI H 2O / H +
i) C6 H 5 NO2 → A 273 K
→ B  A
→C
Fe / HCI HNO2 C6 H 5OH
ii) C6 H 5 NO2 → A 
273 K
→ B  → C
NO2

Fe / HCI NaNO2 + HCI C2 H 5OH 2

iii) → A 
273 K
→ B  → C
Section D
16 Read the following passage and answer the questions. 4
A mixture of two aromatic compounds (A) and (B) was separated by dissolving
in chloroform followed by extraction with aqueous KOH solution. The organic
layer containing compound (A), when heated with alcoholic solution of KOH
produce C7H5N(C) associated with unpleasant odour.
 i) What is A?
ii) The reaction of (A) with alcoholic solution of KOH to produce (C) of
unpleasant odour. What is this reaction called?
iii) The alkaline aqueous layer (B) when heated with chloroform and then
acidified give a mixture of isomeric compounds of molecular formula
C7H6O2. Find the compound (B).
iv) What is (A) and (B) in the following chemical reaction?
CH3CH2NH2 + CHCl3 + 3KOH (A) + (B) + 3H2O.

OR
v) Direct nitration of an aromatic compound (A) is not feasible. Why?

Section E
17 a) i) Explain why an alkylamine is more basic than ammonia? 5
ii) How would you convert?
a) Aniline to nitrobenzene b) Aniline to iodobenzene
b) An aromatic compound ‘A’ on treatment with aqueous ammonia and heating
forms compound ‘B’ which on heating with Br2 and KOH forms a compound
‘C’ of molecular formula C6H7N. Write the structures and IUPAC names of
compounds A, B and C.
OR
a) A primary amine, RNH2 can be reacted with CH3 – X to get secondary
amine, R – NHCH3 but the only disadvantage is that 30 amine and
quaternary ammonium salts are also obtained as side products. Can you
suggest a method where RNH2 forms only 20amine?
b) Describe the following giving the relevant chemical equation in each case:
i) Carbylamine reaction ii) Hofmann’s bromamide reaction