1) Match the compounds in List I with their nature from List II, as seen in aqueous medium from the combinations shown:

a) I—C ; II—C ; III—B ; IV—A
b) |-b ; II—C ; III—C ; IV—A
c) |—c ; II—B ; III—B ; IV—C
d) |-a ; II—A ; III—C ; IV—B

2) Match the compounds in List I with the appropriate test that will be answered by each one of them in List II from the combinations shown :

a) I—A ; II—D ; III—B ; IV—A
b) I—A ; II—D ; III—C ; IV—B
c) I—D ; II—B ; III—C ; IV—A
d) I—B ; II—C ; III—A ; IV—D

3) The reaction by which a primary amine is formed from a primary amide is called the
a) Hofmann reaction
b) Gabriel phthalimide reaction
c) Carbylamine reaction
d) Liebermann nitrosoamine reaction

4) Treatment of ammonia with excess of ethyl iodide will yield
a) Diethylamine
b) Ethylamine
c) Triethylamine
d) Tetraethylammonium iodide

5) What is the end product in the following sequence of operations?

a) Ethyl cyanide
b) Methylamine
c) Ethylamine
d) Acetamide

6) Aniline on heating with conc. HNO3 + conc. H2SO4 mixture yields
a) o- and p-Nitroanilines as the major product
b) m-Nitroaniline as the major product
c) A black tarry matter
d) No reaction

7) A positive carbylamine test is given by
a) N, N-Dimethylaniline
b) 2, 4-Dimethylaniline
c) N-methylbenzylamine
d) Both b and c

8) The dye test can be used to distinguish between
a) Ethylamine and acetamide
b) Ethylamine and aniline
c) Urea and acetamide
d) Methylamine and ethylamine

9) What is the decreasing order of basicity of primary, secondary and tertiary ethylamines and NH3?

10) Acetamide and ethylamine can be distinguished by reacting with
a) Aqueous HCI and heat
b) Aqueous NaOH and heat
d) Bromine water

11) A primary amine can be distinguished from secondary and tertiary amines by the
a) Carbylamine reaction
b) Reaction with methyl iodide
c) Reaction with acetyl chloride
d) None of the above reactions

12) Acetanilide on nitration followed by alkaline hydrolysis mainly gives
a) o-Nitroacetanilide
b) p-Nitroaniline
c) m-Nitroaniline
d) 2, 4, 6-Trinitroaniline

13) Consider the following compounds:

Which of the following statements are correct?

a) I is more basic than II
b) II is more basic than I and III
c) III is more basic than II
d) None of these

14) Which of the following statements is not correct?
b) Amines form hydrogen bonds
c) Ethylamine has higher boiling point than propane
d) Dimethylamine is less basic than methylamine

15) Which of the following gives a primary amine on reduction?

16) Which of the following compounds does not react with NaNO2 and HCI?

17) Hydrolysis of CH3CH2NO2 with 85% H2SO4 gives

18) The following reaction is

a) nucleophilic substitution
b) electrophilic substitution
c) free radical substitution
d) electrophilic addition

19) Aniline when treated with conc. HNO3 gives
a) p-Phenylenediamine
b) Mono-, di-and trinitro-compounds and oxidation products
c) p-Benzoquinone
d) Nitrobenzene

20) Primary amines on heating with CS2 followed by excess of mercuric chloride yields isothiocyanates. The reaction is called
a) Hofmann mustard oil reaction
b) Perkin reaction
c) Fries reaction
d) Diels-Alder reaction

21) The reduction of nitrobenzene with zinc and alkali results in the formation of
a) Aniline
b) Hydrazobenzene
c) Nitrosobenzene
d) Phenylhydroxylamine

22) Which of the following gives the carbylamine reaction?

23) The one which is least basic is

24) On reduction, a secondary amine is given by
a) Nitrobenzene
b) Methylcyanide
c) Nitroethane
d) Methyl isocyanide

25) Cyanide and isocyanide are isomers of the type
a) Positional
b) Functional
c) Tautomer
d) All of these

26) Acetaldoxime reacts with P2O5 (phosphorus pentoxide) to give
a) Methyl cyanide
b) Methyl cyanate
c) Ethyl cyanide
d) None of these

27) Which of the following reacts with chloroform and base to form phenyl isocyanide ?
a) Aniline
b) Phenol
c) Benzene
d) Nitrobenzene

28) Among the following compounds (l-lll), the correct order of reactivity towards electrophilic substitution reaction is

a) II > III > I
b) III < I < II
c) I > II > III
d) I = II > III

29) The compound obtained by heating a mixture of a primary amine and chloroform with ethanolic potassium hydroxide (KOH) is
a) an alkyl isocyanide
b) an alkyl halide
c) an amide
d) an amide and nitro compound

30) Arrange the following: CH3NH2, (CH3)2NH, C6H5NH2, (CH3)3N in increasing order of basicity.
b) Reverse of (a)
d) Reverse of (c)

31) C6H5C = N and C6H5N = C exhibit which type of isomerism ?
a) Position
b) Functional
c) Dextroisomerism
d) Position isomerism

32) Which one of the following is a typical example of a zwitterion ?
a) Aniline
b) Aminophenol
c) Glycine
d) Acetamide

33) Reduction of nitrobenzene in the presence of Zn/NH4C! gives
a) Azobenzene
b) Aniline
c) N-Phenylhydroxylamine
d) Hydrazobenzene

34) The attacking species in the nitration of benzene in te presence of fuming HNO3 is

35) A compound Z reacts with three moles of CH3I and gives a product which on hydrolysis
gives [(CH3)4N]+OH. The compound Z is

d) none

36) By reducing nitrobenzene with Sn + HCI, te product obtained will be
a) Aniline
b) Chlorobenzene
c) Nitrobenzene
d) Phenylhydroxylamine chloride

37) Which reaction sequence would be best to prepare 3-chloroaniline from benzene ?
a) Chlorination, nitration, reduction
b) Nitration, Chlorination, reduction
c) Nitration, reduction, Chlorination
d) Nitration, reduction, acetylation, chlorination, hydrolysis

38) ln the diazotization of arylamines with sodium nitrite and hydrochloric acid, an excess of hydrochloric acid is used primarily to
a) Suppress the concentration of free aniline available for coupling
b) Suppress hydrolysis of phenol
c) Ensure a stoichiometric amount of nitrous acid
d) Neutralise the base liberated

39) Gabriel phthalimide reaction is used for preparation of
a) Primary aromatic amines
b) Secondary amines
c) Primary aliphatic amines
d) Tertiary amines

40) Which of the following is not an explosive ?
a) Nitroglycerine
b) o-Aminotoluene
c) Dynamite
d) Trinitrotoluene

41) Which of the following compounds gives the dye test?
a) Aniline
b) Methylamine
c) Diphenylamine
d) Ethylamine

42) The reaction of nitrous acid with an aliphatic primary amine in the cold gives
a) A diazonium salt
b) An alcohol
c) A nitrite
d) A dye

43) Aniline is reacted with bromine water and the resulting product is treated with an aqueous solution of sodium nitrite in presence of dilute HCI. The compound so formed is converted into tetrafluoroborate which is subsequently heated dry. The final product is
a) p-Bromofluorobenzene
b) p-Bromoaniline
c) 2, 4, 6-Tribromofluorobenzene
d) 1,3, 5-Tribromobenzene

44) Benzenediazonium chloride on reaction with phenol in a weakly basic medium gives
a) Diphenyl ether
b) p-Hydroxyazobenzene
c) Chlorobenzene
d) Benzene

45) Which of the following behaves both as a nucleophile and as an electrophile ?

46) Aniline reacts with NaNO2 and HCI at room temperature to give
a) Nitroaniline
b) Phenol
c) Chloroaniline
d) Diazonium chloride

47) The reaction of benzyl chloride with sodium cyanide followed by reduction with hydrogen in the presence of nickel gives
b) N-lsobutylaniline
c) Benzylamine
d) Aniline

48) Diazonium salts are the reaction products between nitrous acid and
a) Primary aliphatic amines
b) N-Alkyl substituted aromatic amines
c) Primary aromatic amines
d) Secondary amines

49) Among the following compounds, which will react with acetone to give a product containing >C=N—?
d) None of these

50) Nitrosoamines (R2N – N = O) are insoluble in water. On heating with conc. H2SO4, they give secondary amines. This reaction is the basis of the
a) Liebermann nitroso reaction
b) Etard reaction
c) Fries reaction
d) Perkin reaction

51) In the reaction,
the term Y is

a) Acetone
b) Ethanamine
c) Acetaldehyde
d) Dimethylamine

52) Phenyl isocyanide is prepared by which of the following reactions?
b) Carbylamine reaction
c) Reimer-Tiemann reaction
d) Wurtz reaction

53) In the reduction of nitrobenzene, which of the following is the intermediate ?

54) Which of the following reactions will not give a primary amine ?

55) C7H9N has how many isomeric forms that contain a benzene ring ?
a) 4
b) 5
c) 6
d) 7

56) In the sequence, Y can be
a) 4-Nitrochlorobenzene
b) 1-Nitrochlorobenzene
c) 3-Nitrochlorobenzene
d) None of these

57) Identify the product C in the series :

58) The amine that does not react with acetyl chloride is
d) None of these

59) Nitrobenzene on further excessive nitration gives
a) Sym-Trinitrobenzene
b) m-Dinitrobenzene
c) p-Dinitrobenzene
d) All Of these

60) The reaction of C6H5N+2Cl with CuCI gives

61) Primary and secondary amines can be distinguished by
a) Schiffs reagent
b) Carbylamine reaction
c) Hofmann’s bromamide reaction
d) Biuret reaction

62) When benzenediazonium chloride in hydrochloric acid reacts with cuprous chloride, then chlorobenzene is formed. The reaction is called the
a) Gattermann reaction
b) Perkin reaction
c) Etard reaction
d) Sandmeyer reaction

63) Among the following, the strongest base is

64) Which one of the following will be the most basic ?
a) Benzylamine
b) p-Methoxyaniline
c) p-Nitroaniline
d) p-Methylaniline

65) Gabriel synthesis is used for the synthesis of
a) Primary aliphatic amines
b) Secondary amines
c) Aldehydes
d) Acids

66) An organic compound (A) on reduction gives compound (B). (B) on treatment with CHCI3 and alcoholic KOH gives (C). (C) on catalytic reduction gives N-methylaniline. The compound A is
a) Methylamine
b) Nitromethane
c) Aniline
d) Nitrobenzene

67) Unpleasant smelling carbylamines are formed by heating alkali and chloroform with
a) Any aliphatic amine
b) Any aromatic amine
c) Any amine
d) Any primary amine

In the above reaction, X stands for

d) Cl

69) Which of the following reacts with NaNO2 + HCI at 273—278 K to give alcohol/phenol ?

70) Hinsberg reagent is

71) When acetamide is treated with NaOBr, the product formed is

72) Which of the following compounds cannot be identified by the carbylamine test ?

73) The correct order of basicities of the following compounds is
a) 2 > 1 > 3 > 4
b) 1 > 3 > 2 > 4
c) 3 > 1 > 2 > 4
d) 1 > 2 > 3 > 4

74) The compound that will react most readily with NaOH to form methanol is

75) An organic compound with the M.F. C3H5N on hydrolysis forms an acid which reduces Fehlings solution. The compound can be
a) Ethanenitrile
b) Ethyl carbylamine
c) Ethoxyethane
d) Propanenitrile

76) Which of the following has/have an sp2-hybridized nitrogen atom ?
a) Aniline alone
b) Pyrrole alone
c) Pyridine alone
d) All three

77) The product of reaction between chloroform and ethanamine in presence of alcoholic KOH is allowed to react with CI2. The final product is
a) Ethyl chloride
b) Ethylene dichloride
c) Ethyliminocarbonyl chloride
d) Ethanal

78) The product of a reaction between methyl isocyanate (MIC) and ethanol is urethane with the formula

79) Among the following statements on the nitration of aromatic compounds, the false one is:
a) the rate of nitration of benzene is almost the same as that of hexadeuterobenzene
b) the rate of nitration of toluene is greater than that of benzene
c) the rate of nitration of benzene is greater than that of hexadeuterobenzene
d) nitration is an electrophilic substitution reaction

80) Treatment of nitrobenzene with acetyl chloride in the presence of anhydrous AICI3 gives
a) 2-Nitroacetophenone
b) 3-Nitroacetophenone
c) 4-Nitroacetophenone
d) None of the above

81) Acetaldehyde reacts with nitromethane in the presence of dil. NaOH to give
a) 1-Nitro-2-propanol
b) 2-Nitro-1-propanol
c) 2-Nitro-2-propanol
d) None of the above

82) The blasting material amatol is obtained by mixing TNT with

83) m-Bromotoluene is prepared by
a) Bromination of toluene
c) Bromination of nitrobenzene and subsequent replacement of the nitro group with methyl group
d) Bromination of aceto-p-toluidide followed by hydrolysis and deamination

84) Amongst the following, the strongest base is
a) 2, 4, 6-Trinitroaniline
b) 2, 4, 6-Trimethyl-N, N-dimethylaniline
c) For. nitroaniline
d) N, N-Dimethylaniline

85) p-Chloroaniline and aniline hydrochloride can be distinguished by(i) solubility in water; (ii) adding sodium bycarbonate solution; (iii) adding Ag NO3 solution
a) (i) and (iii) only
b) (ii) and (iii) only
c) (ii) alone
d) (i), (ii) and (iii)

86) Ethylamine reacts with nitrosyl chloride (NOCI) to form
a) Ethyl chloride
b) Ethyl alcohol
c) Ethyl nitrite
d) Nitro ethane

87) Gabriel phthalimide synthesis for amino acids involves the reaction between potassium phthalimide and an appropriate a-haloester. For obtaining alanine, the haloester to be used is
a) Ethyl 3-chlorobutyrate
b) Ethyl 3-chloropropionate
c) Ethyl 2-chloropropionate
d) Ethyl chloroacetate

88) In the following compounds:
the order of basicity is

a) IV > I >lll >ll
b) III > I > IV > II
c) ll > l > lll > IV
d) l > III > ll > IV

89) Hydrazobenzene on treatment with H2SO4 gives
a) Azobenzene
b) Benzidine
c) Azoxybenzene
d) Azobenzene-4-sulphonic acid

90) When is heated
a) Propene is the major product
b) Ethene and nitroamine are the only products
c) Ethene and propene are obtained with ethene as the major product
d) Equimolar amounts of ethene and propene are obtained

91) This reaction is called the
a) Cope reaction
b) Ritter reaction
c) Schmidt reaction
d) Gabriel reaction

92) @ Consider p-aminophenol

Which positions are activated for coupling reaction in acidic and basic media respectively ?

a) x in Aand q in B
b) x in A and p in B
c) y in A and p in B
d) y in A and q in B

93) Pyrolysis of gives a

94) Addition of CH3MgBr to HCN followed by acid hydrolysis gives a compound which can also be prepared by
a) LAH reduction of acetonitrile
b) Bubbling the gas produced by the action of water over calcium carbide through.sulphuric acid containing mercury sulphate
c) Dry distillation of calcium acetate
d) Both a and b

95) @ Benzonitrile is obtained when (choose the right answer from A,B,C,D) (i) Benzaldoxime is heated with acetic anhydride, (ii) Benzenediazonium chloride is heated with KCN in presence of Cu powder, (iii) Sodium benzene sulphonate is fused with NaCN
a) (i) and (ii) only
b) (ii) and (iii) only
c) (i) and (iii) only
d) All of the above

96) Depending upon the nature of the reducing agent, the reduction of nitrobenzene under basic conditions may give
a) Azobenzene alone
b) Azoxybenzene alone
c) Hydrazobenzene alone
d) Any one or more of the above

97) The products of reaction of alcoholic silver nitrite with ethyl bromide are
a) Ethane
b) Ethene
c) Nitroethane
d) Ethyl alcohol

98) Which of the following react with both aldehydes/ketones and nitrosobenzene ?
a) alone
b) alone
c) alone
d) All the above

99) Reaction of RCONH2 with a mixture of Br2 and KOH gives RNH2 as the main product. The intermediate involved in the reaction is
b) R— NHBr
d) None of the above

100) Examine the following two structures for the anilinium ion and choose the correct statement from the ones given below:

a) II is not an acceptable canonical structure because N has 10 electrons around it
b) II is not an acceptable canonical structure because it is non-aromatic
c) II is an acceptable canonical structure
d) None of the above


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