1. Aniline whne diazotized in cold and then treated with N, N-dimethylaniline gives a coloured product.

The structure of this

products is

(a)

(b)

(c)

(d)

2. Aniline can be converted into benzylamine by which of the following processes in sequence?
(a)
NaNO 2 +HCl , CuCN , H 2 / Ni
(b)
Br 2 /CCl4 , KCN , LiAlH 4

(c)
HNO 2 , K 2 Cr 2 O7 / H + , Sn+HCl

(d)
CH 3 OH , KMnO4 ,OH − , H +3 O

3. o- Chloroaniline is treated with a mixture of

NaNO 2 and HCl and the product is reacted with cuprous bromide. The final
product in the reaction will be

(a) (b) (c) (d)

4. Coupling of diazonium salts of following takes place in the order

(a) IV>II > III > I (b) IV > III < II <I
(c) II < IV < I < III (d) I <II<III <IV

5. In diazotization reaction of aniline with

NaNO2 and HCl, an excess of HCl is used to
(a) Suppress the formation of acetanilide
(b) Suppress the concentration free aniline available for coupling
(c) Maintain the pH of the reaction
(d) Prevent the formation of anilinium ion.

6. Mark the correct route of the conversion of p-chloroaniline to p-chlorobenzylamine.

(i) (ii) (iii)

(a) Alkylation KCN
H 2 /Pt
(b) Diazotisation CuCN
H 2 /Pt
(c) Oxidation
H 2 /Pt Hydrolysis
+
(d) Diazotisation
H 2 O/ H Sn/ HCl

7. Which of the following is correct method to convert p-toluidine to p-toluic acid?

 (a) Diazotisation, CuCN,
H 2 /Pd
CHCl 3 / NaOH , KCN , Sn /HCl
(b)

Diazotisation,
CuCN /KCN , H 2 O/ H +
(c)
(d) Diazotisation, NaCN,NaOH

8. Amongst the following the strongest base in aqueous medium is _____.

(a)
CH 3 NH 2 (b)
NCCH 2 NH 2

(c)
(CH 3 )2 NH (d)
C 6 H 5 NHCH 3

9. Which of the following reagent would not be a good choice for reducing an aryl nitro compound to an amine?
H /Pt LiAlH
(a) 2( excess) (b) 4 in ether
(c) Fe and HCl (d) Sn and HCl

10. In order to prepare a1 º amine from an alkyl halide with simultaneous addition of one
CH 2 group in the carbon chain, the
reagent used as source of nitrogen is ______.

(a) Sodium amide

NaNH 3
(b) Sodium azide,
NaN 3
(c) Potassium cyanide KCN

(d) Potassium phthalimide,

C 6 H 4 (CO)2 N − K +

11. The source of nitrogen in Gabriel synthesis of amines is

(a) Sodium azide,

NaN 3
(b) Sodium nitrite,
NaNO 2
(c) Potassium cyanide, KCN

(d) Potassium phthalimide,

C 6 H 4 (CO)2 N − K +

12. Amongst the given set of reactants, the most appropriate for preparing 2 º amine is ______

(a)
2 ºR−Br + NH 3
(b) 2 ºR−Br + NaCN followed by
H 2 /Pt
(c)
1 ºR−NH 2 + RCHO followed by
H 2 /Pt
+
(d) 1 ºR−Br (2 mol ) + potassium phthalimide followed by H 3 O /heat

13. The best reagent for converting 2-phenylpropanamide into 2-phenylpropanamine is ___________.
(a) Excess
H2
Br
(b) 2 in aqueous NaOH
(c) Iodine in the presence of red phosphorus
(d)
LiAlH 4 in ether

14. The reagent for converting 2-phenylpropanamide into-1- phenylethanamine is_________.

(a) Excess
H 2 /Pt (b)
NaOH / Br 2
 (c)
NaBH 4 /¿ ¿methanol (d)
LiAl 4 /¿ ¿ether

15. Hofmann bromamide degradation reaction is shown by_______.

(a)
ArNH 2 (b)
ArCONH 2
(c)
ArNO 2 (d)
ArCH 2 NH 2

16. The correct increasing order of basic strength for the following compound is_________.

(a) II < III < I (b) III < I < II

(c) III < II < I (d) II < I < III

17. Methylamine reacts with

HNO 2 to form

(a)
CH 3 −O−N =0 (b)
CH 3 −O−CH 3
(c)
CH 3 OH (d)
CH 3 CHO

18. The gas evolved when methylamine reacts with nitrous acid is ___________.

(a)
NH 3 (b)
N2 (c)
H2 (d)
C2 H6

19. In the nitration of benzene using a mixture of conc. l

H 2 sO4 and conc.
HNO 3 the species which initiates the reaction
is__________.

(a)
NO 2 (b) NO + (c)
NO +2 (d)
NO−2

20. The reaction

Ar N 2 Cl− ⃗
Cu/ HCl ArCl+ N 2 +CuCl
is named as ________.
(a) Sandmeyer reaction (b) Gatterrman reaction
(c) Claisen reaction (d) Carbylamine reaction

21. Best method for preparing primary amines from alkyl halides without changing the number of carbon atoms in the chain is
(a) Hofmann bromamide reaction
(b) Gabriel phthalimide synthesis
(c) Sandmeyer reaction

(d) Reaction with

NH 63

22. Which of the following compounds will not undergo azo coupling reaction with benzene diazonium chloride?
(a) Aniline (b) Phenol (c) Anisole (d) Nitrobenzene

23. Which of the following compounds is the weakest BrÖnsted base?

 (a) (b) (c) (d)

24. Among the following amines, the strongest BrÖnsted base is

(a) (b)
NH 3 (c) (d)

25. The correct decreasing order basic strength of the following species is _________.
H 2 O , NH 3 , OH − , NH −2
(a)
NH −2 >OH − > NH 3 > H 2 O

(b)
OH − > NH −2 > H 2 O> NH 3

(c)
NH 3 > H 2 O> NH −2 >OH −

(d)
H 2 O> NH 3 >OH − > NH −2

26. Which of the following should be most volatile?

(I)
CH 3 CH 2 CH 2 NH 2 (II)
(CH 3 )3 N

(III) (IV)
CH 3 CH 2 CH 3
(a) II (b) IV (c) I (d) III

27. Which of the following methods of preparation of amines will not give same number of carbon atoms in the chain of amines
as in the reactant?
(a) Reaction of nitrite with
LiAlH 4
(b) Reaction of amide with
LiAlH
4 followed by treatment with water
(c) Heating alkyl halide with potassium salt
(d) Treatment of amide with bromine in aqueous solution of sodium hydroxide.

28. Identify the correct pathway to convert propanoic acid to ethylamine. The reagent represented by A, B and C are.
CH 3 CH 2 COOH ⃗A X ⃗B Y C⃗ CH 3
CH 2 NH 2
A B C
(a) Ca (OH )2 Heat
Pt/
H2
(b) SOCl2 NH 3 Br 2 / KOH
(c) HNO 2 P+ I 2 LiAlH 4
(d) HCN NH 3 Br 2 / KOH

29. Identify X, Y and Z in the given reaction:

CH 2 =CH 2 B ⃗r 2 X⃗ NaCN Y ⃗ LiAlH 4 Z
CCl 4 ( 2 moles )

X Y Z
 (a) CH 2 Br−CH 2 Br CH 3 CH 2 CH 3 CH 2
CH 2 CN CH 2 CH 2
NH 2
(b) CH 2 Br−CH 2 Br CH CH CN CH CH
3 2 3 2
CH 2 NH 2
(c) CH 3 CH 2 Br CH 3 CH 2 CN CH 3 CH 2
CH 2 NH 2
(d) CH 2 Br−CH 2 Br NCCH 2 H 2 NCH 2
CH 2 CN CH 2 CH 2
CH 2 NH 2

30. Identify X and Y in the reaction.

(a) ;

(b) ;

(c)

(d)

31. What is the end product in the following sequence of reactions?

(a) Aniline

(b) Phenol

(c) Benzene

(d) Benzenediazonium chloride.

 CH 3 CH 2 Cl ⃗ Ni / H 2 Y ⃗
NaCN X ⃗ Acetic Z .
32. anhydride Z in the above reaction is.

(a)
CH 3 CH 2 CH 2 NHCOCH 3

(b)
CH 3 CH 2 CH 2 NH 2

(c)
CH 3 CH 2 CH 2 CONHCH 3

(d)
CH 3 CH 2 CH 2 CONHCOCH 3

33. Primary amines on reaction with nitrous acid from __ For the test of pimary amines ______ reaction is used. Primary amines
are _____ basic than ammonia.
(a) Carboxylic acids, Hofmann, less

(b) Secondary alcohols, carbylamines, less

(c) Primary alcohols, carbylamines, more

(d) Hydroxylamines, carbylamines, less

34. Match the column I with column II and mark the appropriate choice.
Column I Column II

(A) CH 3 NH 2 +CHCl 3 + KOH ⃗Δ (i) CH 3 NH 2

(B) CH 3 CONH 2 + Br 2 + KOH ⃗ (ii) CH 3 OH
(C) CH 3 NH 2 + NaNO 2 + HCl ⃗Δ (iii) CH 3
NHCH 3
(D) CH 3 NC + 4 H ⃗ Pt (iv) CH 3 NC
(a) (A)→ (i), (B) → (ii), (C) → (iii), (D) → (iv)

(b) (A) → (ii), (B) → (iii), (C) → (iv), (D) → (i)

(c) (A) → (iv), (B) → (i), (C) → (ii), (D) → (iii)

(d) (A) → (iii), (B) → (iv), (C) → (i), (D) → (ii)

35. Which of the following reactions is not correctly metched?

(a) Reaction used to - Hofmann bromamide
convert amide reaction
into primary
amine with one
carbon atom less
(b) Reaction used - Carbylamine reaction
to convert primary
amines into
isocyanides
(c) Reaction used - Hinsberg’s reaction
to distinguish
primary, secondary
and tertiary amines
(d) Preparation of - Victor meyer’s
primary amines synthesis
using phthalimede
36. Identify ‘Z’ in the sequence:
CuCN Y⃗
NaNO 2 +HCl X ⃗
+
C 6 H 5 NH 2⃗ H / H2 O Z
273 K Boil

C H CN
(a) 6 5 (b)
C 6 H 5 CONH 2

C H COOH
(c) 6 5 (d)
C 6 H 5 CH 2 NH 2

37.

Product would be.

(a) (b)

(c) (d)

38. Identify P,Q,R,S,T in the given sequence of reaction.

P Q R

(a)
C 6 H 5 NO 2 C 6 H 5 CN C 6 H 5 NC
S T
C 6 H 5 NH 2 CH 3 COOH
C H
(b) 6 6
C 6 H 5 NO 2 C 6 H 5 NC
C 6 H 5 NH 2 CH 3 COCl
C H NH 2
(c) 6 5
C 6 H 5 NHCH 3 C 6 H 5 NH 2
C 6 H 5 CN CH 3 Cl
C H NO 2
(d) 6 5
C 6 H 5 NH 2 C 6 H 5 NC
C 6 H 5 NHCH 3 ( CH 3 CO ) 2 O

39. An organic compound

(C 3 H 9 N ) (A), when treated with nitrous acid, gave and alcohol and N 2 gas was evolved.
(A) On warming with
CHCl 3 and caustic potash gave (C) which on reduction gave isopropylmethylamine. Predict the
structure of (A).
 (a)

(b)
CH 3 CH 2 −NH −CH 3

(c)

(d)
CH 3 CH 2 CH 2 −NH 2

40. Identify the X and Y in the reaction.

CH 3 −CH −CONH 2⃗
Br 2 / NaOH X⃗
HNO 2 Y
|
CH 3
X =CH 3 −CH −CH 2 NH 2 ; Y =CH 3−CH −CH 2 −OH
| |
CH 3 CH 3
(a)

(b)
X =CH 3 CH =CHNH 2 ; Y =CH 3 CH =CHOH
X =CH 3 −CH −NH 2 ; Y =CH 3−CH −OH
| |
CH 3 CH 3
(c)

(d)
X =CH 3 CH 2 CH 2 NH 2 ; Y =CH 3 CH 2 CH 2 OH

41. Fill in the blanks with appropriate choice of products

(a)

(b)

(c)

(d)

HNO 3 P⃗
C6 H6⃗ Sn / HCl Q⃗
NaNO 2 P⃗
H 3 PO 2 S
H SO HCl H2O
42. 2 4 The end product S in the given sequence of reaction of
reactions is
(a) Benzoic acid (b) Benzene
(c) Phenol (d) Chlorobenzene

43. Match the column I with column II and mark the appropriate choice.
Column I Column II
 (A) Reaction of (i) Sandmeyer
benzene diazonium chloride reaction
with cuprous salts dissolved
in the halogen acid
(B) Reaction of benzene (ii) Gatterman
Diazonium chloride with Reaction
halogen acid in the
presence of copper powder
(C) Reaction of amines with (iii) Hinsberg’s
chloroform reaction
(D) Reaction of (iv) Carbylamine
amines with benzene reaction
sulphonyl chloride
(a) (A)→ (i), (B) → (ii), (C) → (iii), (D) → (iv)

(b) (A) → (iv), (B) → (iii), (C) → (ii), (D) → (i)

(c) (A) → (iii), (B) → (iv), (C) → (i), (D) → (ii)

(d) (A) → (i), (B) → (ii), (C) → (iv), (D) → (iii)

44. Match the column I with column II and mark the appropriate choice.
Column I Column II
(A) (i) Coupling reaction

(B) (ii) Balz-sChiemann

reaction

(C) (iii) Gatterman

reaction

(D) (iv) Sandmeyer

reaction

(a) (A)→ (iv), (B) → (iii), (C) → (ii), (D) → (i)

(b) (A) → (iii), (B) → (iv), (C) → (i), (D) → (ii)

(c) (A) → (ii), (B) → (iii), (C) → (iv), (D) → (i)

(d) (A) → (i), (B) → (ii), (C) → (iii), (D) → (iv)

45. Identify the reagent X, Y, and Z for the following products.

X Y Z
I , warm
(a) 2 KCN, warm NaOH, warm
(b) CuI NaCN KOH
 (c) KI, warm CuCN 2 H O,
warm
(d) AgI, warm AgCN, warm KOH, boil

46. The product ‘D’ in the following sequence of reaction is

(a) 2,4,6-tribromofluorobenzene
(b) Fluorobenzene
(c) p-bromofluorobanzene
(d) tribromobenzene

47. Identify X, Y and Z in the given sequence of reactions.

(a)
X =HBr ; Y =NaNO 2 +HCl ; Z =heat

(b)
X =Br 2 /CCl 4 ; Y =HNO 2 ; Z=CH 3 OH
(c)
X =Br 2 /CuBr ; Y =NaNO 2 + HCl; Z=NaOH
X =Br 2 (aq ); Y =NaNO 2 +HCl(0−4 ºC );
(d)
Z=H 3 PO 2 +H 2 O

48. The structure of product X in the following reaction is

(a) (b)

(c) (d)

49. Match the compounds given in column I with column II and mark the appropriate chice.
Column I Column II
(A) Benzenesulphonyl chloride (i) Zwitter ion
(B) Sulphanilic acid (ii) Hinsberg
reagent
(C) Alkyldiazonium salts (iii) Dyes
(D) Aryldiazonium salts (iv) Conversion to
alcohols
(a) (A)→ (iv), (B) → (iii), (C) → (i), (D) → (ii)

(b) (A) → (ii), (B) → (iv), (C) → (iii), (D) → (i)

 (c) (A) → (ii), (B) → (i), (C) → (iv), (D) → (iii)

(d) (A) → (ii), (B) → (iii), (C) → (iv), (D) → (i)

50. Benzylamine may be alkylated as shown in the following equation :

C 6 H 5 CH 2 NH 2 +R−X ⃗ C6 H 5 CH 2 NHR
S 1
Which of the following alkyl halides is best suited for this reaction through N mechanism?
CH 3 Br (b)
C 6 H 5 Br
(a)
C H CH 2 Br
(c) 6 5 (d)
C 2 H 5 Br