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Amines AK

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I.

Multiple Choice Questions


1. The aromatic primary amine with the formula C7H9N has an incorrect
name.
a) Phenylaminomethane b) Benzylamine c) Benzenamine d)
Phenylmethanamine
2.By reacting with which of the following, primary amines can be
separated from secondary and tertiary amines?
a) Chloroform alone b) Methyl iodide
c) Chloroform and alcoholic KOH d) Zinc dust
3. Which one of the following is the product that is formed when a
primary amine reacts with chloroform in alcoholic KOH?
(a) An isocyanide (b) alcohol (c) An Aldehyde (d) Cyanide
II. Directions: These questions consist of two statements, each printed as
Assertion and Reason. While answering these questions, you are required
to choose any one of the following four responses.
(a) If both Assertion and Reason are correct and the Reason is a correct
explanation of the Assertion.
(b) If both Assertion and Reason are correct but Reason is not a correct
explanation of the Assertion.
(c) If the Assertion is correct but Reason is incorrect.
(d) If both the Assertion and Reason are incorrect
1. Assertion: Aromatic primary amines can be prepared by Gabriel
Phthalimide Synthesis.
Reason: Aryl halides undergo nucleophilic substitution with anion formed
by phthalimide. (d)
2. Assertion : Aniline does not undergo Friedel-Crafts reaction.
Reason : –NH2 group of aniline reacts with AlCl3 (Lewis acid) to give
acid-base reaction. (a)
III. Answer the following questions 5x2=10
1. Arrange the following in the decreasing order of their basic strength in
aqueous solutions: CH3NH2, (CH3)2 NH, (CH3)3N and NH3 (Delhi 2012)
Answer:
(CH3)2 NH > CH3NH2 > (CH3)3 N > NH3
2. Write the structure of (i) 2-aminotoluene. (ii) n-methylethanamine
Answer:
.
H3C—H2C—NH—CH2

3. Arrange the following compounds in increasing order of solubility in water :


C6H5NH2, (C2H5)2NH, C2H5NH2
Answer:
C6H5NH2 < (C2H5)2NH < C2H5NH
4. Identify A and B in each of the following processes
Answer:

5. Complete the following reaction equations


(i) C6H5N2Cl + H3PO2 + H2O →
(ii) C6H5NH2 + Br2 (aq) →
Answer:

IV. Answer the following 5x3=15


1. Describe the following giving the relevant chemical equation in each
case :
(i) Carbylamine reaction
(ii) Hofmann’s bromamide reaction (All India 2012)
Answer:
(i) Carbylamine reaction : Aliphatic and aromatic primary amines on
heating with chloroform and ethanolic KOH form isocyanides or
carbylamines which are foul smelling substances. This reaction is
known as carbylamines reaction.

(ii) Hofmann’s bromamide reaction : Primary amines can be prepared by


treating an amide with Br2 in an aqueous or alcoholic soln of NaOH.

2. How are the following conversions carried out :


(a) Aniline to p-hydroxyazobenzene
(b) Ethanoyl chloride to Ethanenitrile.
Answer:
(a) Aniline to p-hydroxyazobenzene

3. Complete the following reaction equations :


(i) C6H5Cl + CH3COCl →
(ii) C2H5NH2 + C6H5SO2Cl →
(iii) C2H5NH2 + HNO2 →
4. Give the structure of A, B and C in the following reactions: (Delhi
2013)

Answer:

5.
6. Aniline does not undergo Friedel – Crafts reaction.Give reason
V. Answer the following 5x1=5
(i) A compound Z with molecular formula C3H9N reacts with C6H5SO2Cl to give a
solid, insoluble in alkali. Identify Z.
Answer:
C3H9N reacts with C6H5SO2Cl or Hinsberg’s reagent to give a solid, insoluble in alkali,
which means that C3H9N is a secondary amine. The product obtained in this reaction
has no replaceable hydrogen attached to the nitrogen atom of the amine group.
Thus the structure of the given amine is:
(ii) A colourless substance ‘A’ (C6H7N) is sparingly soluble in water and gives a
water-soluble compound ‘B’ on treatment with mineral acid. On reacting with
CHCI3 and alcoholic potash, ‘A’ produces an obnoxious smell due to
compound ‘C’ formation. The reaction of ‘A’ with benzene sulphonyl chloride
gives compound ‘D’, which is soluble in alkali. With NaNO2 and HCI, ‘A’ forms
compound ‘E’, which reacts with phenol in an alkaline medium to give’ F’
orange dye. Identify compounds ‘A’ to ‘F’.
Answer:

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