Address: Branch-I, Main Market, Sector-14, KARNAL & Branch-2: Main Market, CHD City, KARNAL

CHEMISTRY

MULTIPLE CHOICE QUESTIONS–I

1. Which of the following is a 3° amine ? 7. In order to prepare a 1° amine from an alkyl halide with
(a) 1-methylcyclohexylamine simultaneous addition of one CH2 group in the carbon
(b) Triethylamine chain, the reagent used as source of nitrogen is ...........
(c) ierf-butylamine (a) Sodium amide, NaNH2
(d) N-methylaniline (b) Sodium azide, NaN3
2. The correct IUPAC name for CH2 = CHCH2NHCH3 is (c) Potassium cyanide, KCN
(a) Allylmethylamine (d) Potassium phthalimide, C6H4(CO)2N_K+
(b) 2-amino-4-pentene 8. The source of nitrogen in Gabriel synthesis of amines is
(c) 4-aminopent-l-ene ...........
(d) N-methylprop-2-en-l-amine (a) Sodium azide, NaN3
3. Amongst the following, the strongest base in aqueous (b) Sodium nitrite, NaNO2
medium is ........... (c) Potassium cyanide, KCN
(a) CH3NH2 (b) NCCH2NH2 (d) Potassium phthalimide, C6H4(CO)2N-K+
(c) (CH3)2NH (d) C6H5nhCH3 9. Amongst the given set of reactants, the most appropriate
4. Which of the following is the weakest Bronsted base ? for preparing 2° amine is ...........
(a) (b) (a) 2° R—Br + NH3
(b) 2° R—Br + NaCN followed by H2/Pt
(c) 1° R—NH2 + RCHO followed by H2/Pt (d) 1° R—Br (2
(c) (d) CH3NH2 mol) + potassium phthalimide followed by
H3O+/heat
10. The best reagent for converting 2- phenylpropanamide
into 2-phenylpropanamine is ...........
5. Benzylamine may be alkylated as shown in the following (a) excess H2
equation: (b) Br2 in aqueous NaOH
C6H5CH2NH2 + R-X → C6H5CH2NHR (c) iodine in the presence of red phosphorus
Which of the following alkyl halides is best suited for this (d) LiAlH4 in ether
reaction through SN1 mechanism ? 11. The best reagent for converting, 2-phenyl- propanamide
(a) CH3Br (b) C6H5Br into 1-phenylethanamine is...........
(c) C6H5CH2Br (d) C2H5Br (a) excess H2/Pt (b) NaOH/Br2
6. Which of the following reagents would not be a good (c) NaBH4/methanol (d) LiAlH4/ether
choice for reducing an aryl nitro compound to an 12. Hofmann Bromamide Degradation reaction is shown by
amine ? ...........
(a) H2 (excess)/Pt (b) LiAlH4 in ether (a) ArNH2 (b) ArCONH2
(c) Fe- and HCl (d) Sn and HCl (c) ArNO2 (d) ArCH2NH2
13. The correct increasing order of basic strength for the (a) Hofmann bromamide reaction
following compounds is ........... (b) Gabriel phthalimide synthesis
(c) Sandmeyer reaction (d) Reaction with NH3
22. Which of the following compound 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
Bronsted base ?
(a) (b)
(I) (II) (III)
(a) II < III < I (b) HI < I < II
(c) III < II < I (d) II < I < III
14. Methylamine reacts with HNO2 to form...........
(a) CH3—O—N = O (b) CH3—O—CH3 (c) (d)
(c) CH3OH (d) CH3CHO
15. The gas evolved when methylamine reacts with nitrous
acid is...........
(a) NH3 (b) N2 24. Among the following amines, the strongest Bronsted
(c) H2 (d) C2H6 base is ...........
16. In the nitration of benzene using a mixture of cone. (a) (b) NH3
H2SO4 and cone. HNO3, the species which initiates the
reaction is ...........
(a) NO2 (b) NO+
(c) NO+ (d) NO- (i) (d)
17. Reduction of aromatic nitro compounds using Fe and
HCl gives...........
(a) aromatic oxime (b) aromatic hydrocarbon
(c) aromatic primary amine
(d) aromatic amide
18. The most reactive amine towards dilute hydrochloric acid 25. The correct decreasing order of basic strength of the
is ........... following species is ...........
(a) CH3—NH2 (b) H2O, NH3, OH-, 𝑁𝐻2−
(a) 𝑁𝐻2− > OH- > NH3 > H2O
(b) OH- > 𝑁𝐻2− > H2O > NH3
(c) (d) (c) NH3 > H2O > 𝑁𝐻2− > OH-
(d) H2O > NH3 > OH- > 𝑁𝐻2−
26. Which of the following should be most volatile ?
(I) CH3CH2CH2NH2
(II) (CH3)3N
19. Acid anhydrides on reaction with primary amines
(Ill)
give..........
(a) amide (b) imide
(c) secondary amine (d) imine
20. The reaction, Ar Cl- Cu/HCl ArCl + N2 (IV) CH3CH2CH3
(a) II (b) IV
(c) I (d) III
+ CuCl
27. Which of the following methods of preparation of amines
is named as ...........
will not give same number of carbon atoms in the chain
(a) Sandmeyer reaction of amines as in the reactant ?
(b) Gattermann reaction (a) Reaction of alkyl nitrile with LiAlH4.
(c) Claisen reaction (d) Carbylamine reaction (b) Reaction of amide with LiAlH4 followed by treatment
21. Best method for preparing primary amines from alkyl with water.
halides without changing the number of carbon atoms in (c) Heating alkyl halide with potassium salt of phthalimide
the chain is followed by hydrolysis.
2
(d) Treatment of amide with bromine in aqueous solution of
sodium hydroxide.
ASSERTION AND RESON
Note: 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 wrong.
(b) Both assertion and reason are correct statements but reason is not correct explanation of assertion.
(c) Assertion is correct statement but reason is wrong statement.
(d) Both assertion and reason are correct statements and reason is correct explanation of assertion.
(e) Assertion is wrong statement but reason is correct statement.
1. Assertion: Acylation of amines gives a monosubstituted product whereas alkylation of amines gives polysubstituted
product.
Reason: Acyl group sterically hinders the approach of further acyl groups.
2. Assertion: Hofmann’s bromamide reaction is given by primary amines.
Reason: Primary amines are more basic than secondary amines.
3. Assertion: N-Ethylbenzenesulphonamide is soluble in alkali.
Reason: Hydrogen attached to nitrogen in sulphonamide is strongly acidic.
4. Assertion: N, N-Diethylbenzenesulphonamide is insoluble in alkali.
Reason: Sulphonyl group attached to nitrogen atom is a strong electron withdrawing group.
5. Assertion: Only a small amount of HCl is required in the reduction of nitro compounds with iron scrap.
Reason: FeCl2 formed gets hydrolysed to release HCl during the reaction.
6. Assertion: Aromatic 1° amines can be prepared by Gabriel Phthalimide Synthesis.
Reason: Aryl halides undergo nucleophilic substitution with anion formed by phthalimide.
7. Assertion: Acetanilide is less basic than aniline.
Reason: Acetylation of aniline results in decrease of electron density on nitrogen.
ANSWERS
Multiple Choice Questions -1
1. (b) 2. (d) 3. (c) 4. (a) 5. (c) 6. (b) 7. (c) 8. (d) 9. (c) 10. (d)
11. (b) 12. (b) 13. (d) 14. (c) 15. (b) 16. (c) 17. (c) 18. (b) 19. (a) 20. (b)
21. (b) 22. (d) 23. (c) 24. (d) 25. (a) 26. (b) 27. (d)
ASSERTION AND REASON
1. (c) 2. (a) 3. (d) 4. (b) 5. (d) 6. (a) 7. (d)

3
 HINTS FOR DIFFICULT MULTIPLE CHOICE QUESTIONS
ASSERTION AND REASON
1. Correct reason. Due to delocalization of the lone pair of electrons of the N-atom over the carbonyl group in the acyl
derivative, the electron density on the N-atom decreases to such an extent that it does not act as a nucleophile at all and
hence does not react with another molecule of the acylating agent.
2. Correct assertion. Hofmann’s bromamide reaction is given by 1° amides.
Correct reason. With Br2/NaOH, primary amides are converted into isocyanates which upon alkaline hydrolysis give primary
amines.
3. Reason is the correct explanation of the assertion.
4. Correct explanation. Since acidic hydrogen is not present on the N-atom, therefore, N, N- diethylbenzenesulphonamide is
insoluble in alkali.
5. Reason is the correct explanation of the assertion.
6. Correct assertion. Aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis. Correct reason. Aryl
halides do not undergo nucleophilic substitution with anion formed by phthalimide.
7. Reason is the correct explanation of the assertion.
Multiple Choice Questions -1
1. (C2H5)3N (CH3)3C—NH2

1° amine 3° amine 1° amine 2° amine

Thus, option (b) is correct.
2. H2NHCH3 N-Methylprop-2-en-l amine

3. 2° Amines are more basic than 1°, i.e., (CH3)2NH is more basic than CH3NH2. Due to -1-effect of CN group, NCCH2NH2
is less basic than even CH3NH2. C6H5NHCH3 is less basic than both CH3NH2 and (CH3)2NH due to delocalization of
lone pair of electrons on the N-atom into the benzene ring.
4. Due to delocalisation of a lone pair of electrons present on the N-atom into the benzene ring, C6H5NH2 is the weakest base.
5. Since C6H5CH2Br on ionization gives a resonance stabilized benzyl carbocation (C6H5𝐶𝐻2+ .therefore, C6H5CH2Br is best
suited for SN1 reaction,
6. LiAlH./ether reduces aryl nitro compounds to azo compounds, i.e.,
2 C6H5NO2 LiAlH4/ether C6H5N = NC6H5

Nitrobenzene Diazobenzene
7. Cyanides on reduction give 1° amines with one more CH2 group, i.e.,
R—X R—CN Na/C,H,OH R — CH2NH2

8. C6H4(CO)2N- K+.
9. R—NH2 + RCHO [R—N = CHR] H2/Pt R—NH—CH2R

2° Amine
10. LiAlH4/ether

2-Phenylpropanamide 2-Phenylpropanamine

11.

2-Phenylpropanamide 1 -Phenylethanamine
13. Electron-donating groups (i.e., CH3) increase while electron-withdrawing groups (i.e., NO2) decrease the basicity of
amines. Thus, option (d) is correct.
18. The amine which is most basic is most reactive, i.e., (CH3)2NH.
19. Amides are formed
4
(RCO)2O + RNH2 → RCONH2 + RCOOH
22. Diazonium cation is a weak electrophile and hence reacts with electron rich compounds containing electron donating
groups such as -OH, -NH2 and -OCH3 groups and not with compounds containing electron withdrawing groups such as
NO2, etc.
23. Amines (a, b) have a stronger tendency to accept a proton and hence are stronger Bronsted bases than phenol (c) and
alcohol (d). Since phenol is more acidic than alcohol, therefore, phenol (c) has the least tendency to accept a proton and
hence it is the weakest Bronsted base.
24. Aniline is a weaker base than NH3 due to delocalization of lone of pair electrons of the N atom over the benzene ring.
Pyrrole (c) is not at all basic because the lone pair of electrons on the N-atom is donated towards aromatic sextet
formation. Therefore, pyrrolidine (d) has a strong tendency to accept a proton and is hence it is the strongest Bronsted
base.
25. NH3 is more basic than H2O, therefore, NH2 is a stronger base than OH . Thus, the decreasing order of basic strength is
option (a), i.e., 𝑁𝐻2− > OH- > NH3 > H2O.
26. 1o and 2° Amines due to intermolecular H-bonding have higher boiling points (and hence less volatile) than 3° amines
and hydrocarbons of comparable molecular mass. Further, due to polar C-N bonds, 3° amines are more polar than
hydrocarbons which are almost non-polar. Therefore, due to weak dipole- dipole interactions, 3° amines have higher
boiling point (i.e., less volatile) than hydrocarbons. In other words, CH 3CH2CH3 has the least b.p. and hence is most
volatile.
27. Only treatment of amide with Br2 in aqueous solution of NaOH will give an amine with lesser number of carbon atoms
than in the reactant while
RCONH2 Br2/NaOH RNH2

all the remaining reactions give an amine with the same number of carbon atoms as in the reactant.