Beruflich Dokumente
Kultur Dokumente
Amines
Solutions
SECTION - A
Objective Type Questions
(Classification and Nomenclature of Amines)
CH3
H
1. CH3 C N is a
H
CH3
(1) Primary amine (2) Secondary amine (3) Tertiary amine (4) Ammonium salt
Sol. Answer (1)
NH2
NH
CH3
N-methyl prop-2-ene 1-amine
4. A secondary amine is
(1) A compound with two –NH2 group
(2) A compound with two carbon atoms and a –NH2 group
(3) A compound with a –NH2 group on the carbon atom in number two position
(4) A compound in which two of the hydrogens of NH3 have been replaced by alkyl or aryl groups
Sol. Answer (4)
CH 3 – N – CH 3 is secondary amine.
H
(Preparation of Amines)
O
C – NH2 will show Hoffmann degradation reaction.
6. Best method for preparing primary amines from alkyl halides without changing the number of carbon atoms
in the chain is
(1) Hoffmann bromamide reaction (2) Gabriel phthalimide synthesis
(3) Sandmeyer reaction (4) Reaction with NH3
Sol. Answer (2)
1° amine can be prepared by Gabriel phthalimide reaction
8. When acetamide is treated with Br2 and caustic soda, then we get
(1) Bromoacetic acid (2) Acetic acid (3) Methylamine (4) Ethane
Sol. Answer (3)
O
–
Br21OH
CH 3 – C – NH 2 CH 3 – NH 2
Reduction
9. CONH2 CH2NH2
In above reaction hybridisation state of carbon changes from
2 3
(1) sp sp (2) sp sp (3) sp2 sp
3
(4) sp2 sp
Sol. Answer (3)
O
Reduction
– C – NH2 – CH2NH2
2 2
sp sp
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Solutions of Assignment (Set-2) Amines 229
10. A compound ‘A’ when treated with HNO3 (in presence of H2SO4) gives compound B, which is then reduced
with Sn and HCl to aniline. The compound is
(1) Toluene (2) Benzene (3) Ethane (4) Acetamide
Sol. Answer (2)
Nitration Sn/4HCl
NO2 NH2
(Benzene) (Aniline)
NH2
13. Aliphatic amines are ______ basic than NH3 but aromatic amines are ______ basic than NH3.
(1) More, less (2) Less, more (3) More, more (4) None of these
Sol. Answer (1)
Because in aromatic amine lone pair is in conjugation with benzene ring.
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230 Amines Solutions of Assignment (Set-2)
16. The correct increasing order of basic strength for the following compounds is
NH2 NH2 NH2
NO2 CH3
(I) (II) (III)
(1) II < III < I (2) III < I < II (3) III < II < I (4) II < I < III
Sol. Answer (4)
NH2 NH2 NH2
CH3 NO2
(+H) (–M)
Basic strength
NO2
18. The decreasing order of the basic character of NH3, CH3NH2, C2H5NH2 and C6H5NH2 is
(1) NH3 > CH3NH2 > C2H5NH2 > C6H5NH2 (2) C2H5NH2 > CH3NH2 > NH3 > C6H5NH2
(3) C6H5NH2 > C2H5NH2 > CH3NH2 > NH3 (4) CH3NH2 > C2H5NH2 > C6H5NH2 > NH3
Sol. Answer (2)
N
is least basic
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Solutions of Assignment (Set-2) Amines 231
20. Strongest base is
(1) CH2 = CH – CH2 – NH2 (2) CH C – CH2 – NH2
NH2
NH2 is the strongest base among the other shown bases because of max e– density over N-atom.
NH2 NH2
NH2
resonance
CH2
(1) CH3CH2CH2NH2 (2) (CH3)3N (3) NH (4) CH3OH
CH 3
CH3
N is most volatile in above choices
CH3 CH3
O O
NH2+ NH–C–CH3
Cl acetanilide
24. The compound obtained by heating a mixture of a primary amine and chloroform with ethanolic potassium
hydroxide is
(1) An alkyl isocyanide (2) An alkyl halide
(3) An amide (4) An amide and nitro compound
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232 Amines Solutions of Assignment (Set-2)
OH−
R – NH2 + CHCl3 ⎯⎯⎯ → R − N= C
alkyl isocyanide
25. A compound X has the molecular formula C7H7NO. On treatment with Br2 and KOH, X gives an amine Y.
The latter gives carbylamine test. Y upon diazotisation and coupling with phenol gives an azo dye. Thus X
is
(1) C6H5CONH2 (2) C6H5CH2NO (3) C6H5COONH4 (4) All of these
Sol. Answer (1)
O
C – NH2 – Br2, OH– NH2
Y
–
N= C CHCl3, OH
26. An organic compound (A) on reduction gave a compound (B). Upon treatment with HNO2, (B) gave ethyl
alcohol and on warming with CHCl3 and alcoholic KOH, (B) gave an offensive smell. The compound (A) is
(1) CH3NH2 (2) CH3NC (3) CH3CN (4) C2H5CN
Sol. Answer (3)
[H] HONO
CH3CN NH2 OH
–
CHCl3, OH
CH3–CH2–N =C
27. An amine reacts with C6H5SO2Cl and the product is soluble in alkali, amine is
(1) 1° amine (2) 2° amine (3) 3° amine (4) All of these
Sol. Answer (1)
O O
R–NH2 + Cl–S– R–N–S–
(1°)
O H O
Base
Soluble
28. Which would not react with benzene sulphonyl chloride in aqueous NaOH?
(1) Aniline (2) N, N-dimethylaniline (3) p-toluidine (4) N-ethyl aniline
Sol. Answer (2)
Me O
N + Cl–S Because of lack of H on nitrogen.
Me
O
No reaction
29. A mixture of 1°, 2° and 3° amines can be separated by Hinsberg’s reagent which is
(1) Benzoyl chloride (2) Acetyl chloride
(3) Benzene sulphonyl chloride (4) Benzyl chloride
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Solutions of Assignment (Set-2) Amines 233
Sol. Answer (3)
Hinsberg's reagent
O
–S–Cl
O
Benzene sulphonyl chloride
NHCOCH3
HNO3 H2O
Intermediate X
H2SO4
O
NH–C–CH3 NH–C–CH3 NH2
O Nitration H2O
NO2
Br
H2O
–NH2 + Br2 Br – NH2
Br
35. The strongest ortho-para and strongest meta directing groups are respectively
(1) –NO2 and –NH2 (2) –CONH2 and –NH2 (3) –NH2 and –NO2 (4) –NH2 and CONH2
Sol. Answer (3)
– NH2 Strongest o/p directing because of + R nature
– NO2 Strongest m directing because of – R nature
(Diazonium Salts, Cyanides and Isocyanides)
36. Which of the following forms a stable diazonium salt at 273 - 278 K?
(1) Ethylamine (2) Aniline (3) Dimethylamine (4) Benzylamine
Sol. Answer (2)
NaNO2 , dil HCl
NH2 N2+Cl–
O–5°C
37. Reaction of nitrous acid with aliphatic primary amine in the cold gives
(1) A diazonium salt (2) An alcohol (3) A nitrite (4) A dye
Sol. Answer (2)
R–NH2 + HONO R–OH
(Alcohol)
38. The gas evolved when methylamine reacts with nitrous acid is
(1) NH3 (2) N2 (3) H2 (4) C2H6
Sol. Answer (2)
CH3NH2 + 2HNO2 C-H3–O–N =O + N2 + H2O
Methyl nitrite
2CH3NH2 + 2HNO2 CH3–O–CH3 + 2N2 + 3 H2O
Methoxy methane
1° Amine reacts with nitrous acid to form alcohol except methyl amine at ordinary temperature.
(1) CH3 – O – NO (2) CH3 – CH2 – NO2 (3) CH3CH2CN (4) CH3 – CH – CH
CH3
Sol. Answer (2)
O OH
CH3 – CH2 – N CH3 – CH = N
O O
Nitro form Aci form
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Solutions of Assignment (Set-2) Amines 235
40. Benzenediazonium chloride on reaction with water gives
(1) Phenol (2) Aniline (3) Benzylamine (4) Benzaldehyde
Sol. Answer (1)
N2+Cl– + H2O OH
41. Benzenediazonium chloride on reaction with phenol in weakly basic medium gives
(1) Diphenyl ether (2) p-Hydroxyazobenzene (3) Chlorobenzene (4) Benzene
Sol. Answer (2)
OH
–
+ – OH
N2 Cl + OH
N
N
42. When benzenediazonium chloride is heated with fluoro boric acid, fluorobenzene is formed. This reaction is
called
(1) Balz Schiemann reaction (2) Gattermann reaction
(3) Sandmeyer reaction (4) Hofmann bromamide reaction
Sol. Answer (1)
+ – + –
N2 Cl + H BF4 F
+
N2 Cl– + H3PO2
(Benzene)
44. Diazotisation can be carried out by the action of NaNO2 and dilute HCI at ice cold temperature
(1) Aromatic secondary amine
(2) Aromatic primary amine
(3) Aromatic nitro compound
(4) Aliphatic amine
Sol. Answer (2)
O–5°C
NH2 + HONO NH2+ C–
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236 Amines Solutions of Assignment (Set-2)
45. When benzene diazonium chloride is treated with cuprous chloride and HCI the product formed is
(1) Chlorobenzene (2) Benzene
HCl
N2+Cl– + Cu2Cl2 Cl (Sandmeyr's reaction)
+ –
N2 Cl
N2+Cl– CN COOH
+
CuCN H NaOH
H2O Cao,
SECTION - B
Objective Type Questions
(Preparation of Amines)
1. Which one of the following on reduction with lithium aluminium hydride yields a secondary amine?
(1) Methyl isocyanide (2) Acetamide (3) Methyl cyanide (4) Nitroethane
Sol. Answer (1)
Me
CH3N = C + LiAlH4 NH
Me
(2°) amine
2. The reaction of the benzyl chloride with sodium cyanide followed by reduction with hydrogen in the presence of
nickel gives
(1) -phenyl ethylamine (2) N-isobutylaniline (3) Benzyl amine (4) Aniline
Sol. Answer (1)
– [H]
+ CN
Cl CN NH2
(-phenyl
ethylamine)
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Solutions of Assignment (Set-2) Amines 237
3. Amine is obtained as major product in
CH3
NH3 NaNH2
(1) Cl (2) CH3 CH2 CH CH3 NH3
O Cl
LiAlH4
(3) CH 3 C NH CH3 (4) All of these
O O
COOH CO C
NH O
(1) (2) NH (3) (4)
COOH CO C NH NH
O O
O O
+ NH2NH2, EtOH
O
NH
R – NH2 +
NH
O
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238 Amines Solutions of Assignment (Set-2)
7. C7H9N has how many isomeric forms that contain a benzene ring?
(1) 4 (2) 5 (3) 6 (4) 7
Sol. Answer (2)
NH2
NH2 NH2
CH3
CH3 CH3
NH – CH3 CH2 – NH2
8. R–NH 2 + CH 3COCl A.
(excess)
O O
R–NH2+CH3–C–Cl R–NH–C–CH3
10. Alanine, the amino acid the respective structure at pH = 2 and pH = 10 will be
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Solutions of Assignment (Set-2) Amines 239
Sol. Answer (3)
CH3
+
At PH = 2 : H3N – CH – COOH
CH3
At PH = 10 : NH2 – CH – COO–
11. Which product is formed, when acetonitrile is hydrolysed partially with cold concentrated HCl?
(1) Methyl cyanide (2) Acetic anhydrides
(3) Acetic acid (4) Acetamide
Sol. Answer (4)
O
partially
CH3CN + H2O CH3 – C – NH2
12. Which of the following pair make fastest coupling reaction in acidic medium?
NO2 N2+Cl– +
N
N
NO2
+ –
NH2 + HONO N2 Cl
(Stable)
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240 Amines Solutions of Assignment (Set-2)
CONH2 CONH2
(1) (2)
NO2 OCH3
CONH2 CONH2
(3) (4)
CH3 Cl
COCH3
is most reactive because the Migration step is RDS step and assisted by (+M) of –OCH3 at p-
OCH3
position.
NO2
+
KCN H2O/H
A B
15. .
Br
NO2 COOH
NO2 COOH
COOH COOH Br Br
NO2
+
KCN H2O/H
A B
COOH
COOH
B is
Br
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Solutions of Assignment (Set-2) Amines 241
Mechanism
(1) HNO2 acid (2) CHCl3 /KOH (3) Br2 water (4) Schiff ’s reagent
NH2
NH2
CH3 CH3
N
1
2
NO2
(NH4)2S NaNO2 /
18. (A) (B)
HCl, 0ºC
NO2
H3O+ CuCN/
(D) (C)
HCN
The above reaction sequence (D) is
NO2
N(CH3)2
HNO2
19. A . The product A will be
N(CH3)2 N(CH3)2
NO2 O=N–NCH3
20. Write the correct order of the following diazonium cations for the coupling with phenol
N2+ N2+ N2+ N2+
OCH3
CH3 NO2
I II III IV
(1) III > IV > I > II (2) II > I > IV > III (3) III > I > II > IV (4) II > IV > I > III
Sol. Answer (1)
The order of reactivity for coupling with phenol is
+ + + +
N2 N2 N2 N2
OCH3
NO2 CH3
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Solutions of Assignment (Set-2) Amines 243
SECTION - C
1. Nitration of aniline in strong acidic medium also gives m-nitroaniline because [NEET-2018]
(1) Inspite of substituents nitro group always goes to only m-position.
(2) In electrophilic substitution reactions amino group is meta directive.
(3) In acidic (strong) medium aniline is present as anilinium ion.
(4) In absence of substituents nitro group always goes to m-position.
Sol. Answer (3)
NH2 NH3
Anilinium ion
–NH3 is m-directing, hence besides para (51%) and ortho (2%), meta product (47%) is also formed in
significant yield.
2. The correct increasing order of basic strength for the following compounds is [NEET-2017]
NO2 CH3
(I) (II) (III)
(1) II < III < I (2) III < I < II (3) III < II < I (4) II < I < III
Sol. Answer (4)
–NO2 has strong –R effect and –CH3 shows +R effect.
Order of basic strength is
< <
NO2 CH3
3. Which of the following reactions is appropriate for converting acetamide to methanamine? [NEET-2017]
(1) Carbylamine reaction (2) Hoffmann hypobromamide reaction
(3) Stephens reaction (4) Gabriels phthalimide synthesis
Sol. Answer (2)
O
CH3 – C – NH2 + Br2 + 4NaOH CH3 – NH2 + 2NaBr + Na2CO3 + 3H2O
This is Hoffmann Bromamide reaction.
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244 Amines Solutions of Assignment (Set-2)
4. Which one of the following nitro-compounds does not react with nitrous acid? [NEET-(Phase-2)-2016]
H2 H2 CH3
H3C C H3C C H3C
(1) C NO2 (2) CH NO2 (3) H3C C NO2 (4) H3C C
H2 H3C H NO2
H3C
O
Sol. Answer (3)
CH3
H3C C NO2
CH3
No acidic H-atom on the carbon atom having NO2-group.
5. A given nitrogen-containing aromatic compound A reacts with Sn/HCl, followed by HNO2 to give an unstable
compound B. B, on treatment with phenol, forms a beautiful coloured compound C with the molecular formula
C12H10N2O. The structure of compound A is [NEET-(Phase-2)-2016]
OH
6. The product formed by the reaction of an aldehyde with a primary amine is [NEET-2016]
(1) Aromatic acid (2) Schiff base (3) Ketone (4) Carboxylic acid
Sol. Answer (2)
O H
R C H + RNH2 R C N R+ H2O
schiff base
NH2
R NH2
Cl
10. The electrolytic reduction of nitrobenzene in strongly acidic medium produces [AIPMT-2015]
(1) Aniline (2) p-Aminophenol (3) Azoxybenzene (4) Azobenzene
Sol. Answer (2)
OH
NH2
(p-Aminophenol)
NH 2
(1) N=N–NH (2) N=N
NH2
(3) N=N (4) N=N NH2
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246 Amines Solutions of Assignment (Set-2)
–
12. Which of the following will be most stable diazonium salt RN2 X ? [AIPMT-2014]
–
(1) CH3N2 X (2) C6H5N2 X– (3) CH3 CH2 N2 X– (4) C H CH N2 X–
6 5 2
13. Nitrobenzene on reaction with conc. HNO3/H2SO4 at 80–100°C forms which one of the following products?
[NEET-2013]
(1) 1,3-Dinitrobenzene (2) 1,4-Dinitrobenzene (3) 1,2,4-Trinitrobenzene (4) 1,2-Dinitrobenzene
Sol. Answer (1)
NO2
NO 2
A
14. In the reaction Br
+ Br
N2Cl
A is [NEET-2013]
+
(1) Cu2Cl2 (2) H3PO2 and H2O (3) H /H2O (4) HgSO4/H2SO4
Sol. Answer (2)
15. An organic compound (C3H9N) (A), when treated with nitrous acid, gave an alcohol and N2 gas was evolved.
(A) on warming with CHCl3 and caustic potash gave (C) which on reduction gave isopropylmethylamine. Predict
the structure of (A) [AIPMT (Mains)-2012]
CH 3
(1) CH–NH2 (2) CH3CH2–NH–CH3 (3) CH 3–N–CH 3 (4) CH3CH2CH2–NH2
CH3
Sol. Answer (1) CH3
CH3
CH – NH2
CH3
NO2
Zn
16. What is the product obtained in the following reaction:
NH Cl
...........?
4
[AIPMT (Prelims)-2011]
NH2 NHOH
(1) (2)
–
N O
N-phenylhydroxylamine
18. Acetamide is treated with the following reagents separately. Which one of these would yield methylamine?
[AIPMT (Prelims)-2010]
(1) NaOH – Br2 (2) Sodalime (3) Hot conc. H2SO4 (4) PCl5
Sol. Answer (1)
O
Br2/OH
CH3 NH2 CH3 – NH2
19. Which of the following statements about primary amines is 'False'? [AIPMT (Prelims) -2010]
(1) Alkyl amines are stronger bases than aryl amines
(2) Alkyl amines react with nitrous acid to produce alcohols
(3) Aryl amines react with nitrous acid to produce phenols
(4) Alkyl amines are stronger bases than ammonia
Sol. Answer (3)
Aryl amines react with nitrous acid to form diazonium salt.
20. Aniline in a set of the following reactions yielded a coloured product 'Y'
NH2
NaNO2/HCl N, N-dimethylaniline
X Y
(273 – 278K)
The structure of 'Y' would be [AIPMT (Prelims)-2010]
CH3 CH3
CH3
(1) N=N N (2) HN NH NH
CH3
CH3 CH3
21. Match the compounds given in Column-I with their characteristic reactions given in Column-II. Select the correct
option
Column-I Column-II
(Compounds) (Reactions)
a. CH3CH2CH2CH2NH2 (i) Alkaline hydrolysis
b. CH3C CH (ii) With KOH (alcohol) and CHCl3 produces bad smell
c. CH3CH2COOCH3 (iii) Gives white ppt. with ammoniacal AgNO3
d. CH3CH(OH)CH3 (iv) With Lucas reagent cloudiness appears after 5 minutes
[AIPMT (Mains)-2010]
(1) a(ii), b(i), c(iv), d(iii) (2) a(iii), b(ii), c(i), d(iv) (3) a(ii), b(iii), c(i), d(iv) (4) a(iv), b(ii), c(iii), d(i)
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248 Amines Solutions of Assignment (Set-2)
KOH CHCl
H3C CH2 CH2 CH2 NH2
3
H3C CH2 CH2 CH2 NC
It reacts with KOH (alcohol) and CHCl3 produces (1° R – NH2) bad smell (isocyanide)
b (iii)
AgNO
H3C C C H 3
H3C C C Ag HNO3
White ppt.
acidic‘H’
c (i)
NaOH(aq.)
H3C CH2 C OCH3 H3C CH2 C OH + H3COH
d (iv)
H3C CH CH3 gives test with Lucas reagent cloudiness appears after 5 minutes.
H CH 3
N + HONO N
CH3 N=O
CH3
(1) N=N N (2) N=N CH2–N
CH3
CH2
CH3 CH3
CH3
N=N NH=NH N
(3) (4) CH3
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Solutions of Assignment (Set-2) Amines 249
Sol. Answer (1)
CH3 CH3
CH3 N
N
CH3
HONO +
NH2 N2
24. Which one of the following on reduction with lithium aluminium hydride yields a secondary amine ?
[AIPMT (Prelims)-2007]
(1) Methyl cyanide (2) Nitroethane (3) Methylisocyanide (4) Acetamide
Sol. Answer (3)
25. Which of the following is more basic than aniline ? [AIPMT (Prelims)-2006]
(1) Diphenylamine (2) Triphenylamine (3) p-Nitroaniline (4) Benzylamine
Sol. Answer (4)
27. The major organic product formed from the following reaction
O
(i) CH3NH2
(ii) LiAIH (iii) H O
......... is [AIPMT (Prelims)-2005]
4 2
28. Electrolytic reduction of Nitrobenzene in weakly acidic medium gives [AIPMT (Prelims)-2005]
(1) Aniline (2) Nitrosobenzene
(3) N-phenylhydroxylamine (4) p-Hydroxyaniline
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250 Amines Solutions of Assignment (Set-2)
30. What will be the final product in the following reaction sequence?
NH
H /H2O
A B
3 NaOBr
CH3CH2CN C
32. The compound obtained by heating a mixture of ethyl amine and chloroform with ethanolic potassium hydroxide
(KOH) is
(1) An amide (2) An amide and nitro compound
(3) An ethyl isocyanide (4) An alkyl halide
Sol. Answer (3)
–
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Solutions of Assignment (Set-2) Amines 251
35. Diazo-coupling is useful to prepare some
(1) Dyes (2) Vitamins (3) Pesticides (4) Proteins
Sol. Answer (1)
Diazo coupling gives Dyes.
CHCl3 /KOH
39. A
Reduction
B C
Reduction
N– methyl aniline.
Then A is
NH2 NO2 NC
CH3
would be
O O
NH2 NH–C–CH3 NH–C–CH3 NH2
Br Br
Br2, AlOH H2O
+ Al2O
H+
41. Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO3 and conc. H2SO4. In the
mixture, nitric acid acts as a/an
(1) Catalyst (2) Reducing agent (3) Acid (4) Base
Sol. Answer (4)
+ +
HNO3 + H2SO4 H – O – NO2 NO2
(Nitronium
H
ion)
HNO3 is acts as a base.
42. How many isomers of molecular formula C3H9N will liberate N2 gas on treatment with HNO2?
(1) One (2) Three (3) Two (4) Five
Sol. Answer (3)
NH2 HONO
N2
(10)
NH2
HONO
N2
(1°)
NO2
(NH4)2S Br2
43. (A) CH3COOH
(B) .
NO2
NO2 AlOH
NO2 NO2
O OH
CH3 – CH – N CH3 – CH = N
O O
CH3 – C – NH2 CH2 = C – NH2
O OH
O OH
N2Cl
NaNO2/HCl H3PO4
(A) (B) – (C)
OH
NH2
OH
(1) (2)
NH OH
N=N N=N
(3) (4)
OH HO NH2
Sol. Answer (3)
N2+
HONO H2O
+ Boiling
N=N OH
NH2 NH2 OH
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254 Amines Solutions of Assignment (Set-2)
SECTION - D
Assertion-Reason Type Questions
1. A : Arene diazonium salts are more stable than alkane diazonium salts.
In NH2 NH2 is highly ring activating group. (Powerful ortho and para director).
R R R
+
KMnO4 H2O/H
CH NH2 CH NH CH O
–H2
R H R
2° amine to Tetraalkylhydrazine
R R R
KMnO4
2 NH N N
–H2
R R R
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Solutions of Assignment (Set-2) Amines 255
6. A : Aniline is not prepared by Gabriel phthalimide synthesis.
R : Due to partial double bond character in haloarene because of resonance.
Sol. Answer (1)
8. A : Primary aliphatic amines react with CS2 and HgCl2, give precipitate of HgS.
R : Secondary amine does not give precipitate of HgS in this reaction.
Sol. Answer (2)
– + – S
HgCl2
R NH H + C S R NH C SH R N C S + HgS + 2HCl
Alkyl isothiocyanate Mustard oil smell.
R S R S
NH + C S N C SH
R R
2° amine N2N dialkyldithiocarbamic acid
9. A : In Hofmann's bromamide degradation amines formed containing one carbon atom less than carbon atoms
present in amide.
R : This reaction occurs through the formation of nitrine intermediate.
Sol. Answer (3)
The reaction takes place high high formation of Alkyl Isocyanate which on hydrolysis yield 1° amine with one C
less.
10. A : Reaction of carboxylic acid with hydrazoic acid in the presence of conc. H2SO4 to form primary amine is
called Schmidt reaction.
R : In this reaction isocyanate intermediate is formed.
Sol. Answer (2)
O
+
H HN3 –N2
Ar COOH Ar C O Ar C NH N N +
H2O –H
Hydrolysis
Ar N C O Ar NH2
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256 Amines Solutions of Assignment (Set-2)
OH OH N2Cl
OH
12. A : is less reactive than in coupling reaction with .
OH
OH
O
R : Formula of urethane is NH2 C NH OCH2CH3 .
A : It is correct as
O O
NH2 C OC2H5 + NH3 NH2 C NH2 + C2H5OH
(Urethane) (Urea)
It is nucleophilic substitution.
O
R : It is wrong as Urethane is NH2 – C – O – C2H5 .
N2Cl
R : It is Sandmeyer's reaction.
CuX/HCl
N2Cl (Sandmeyer's reaction)
X Cl, for CN
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Solutions of Assignment (Set-2) Amines 257
Sol. Answer (1)
H
N
A and R both are correct. In pyrrole , the lone pair is in conjugation with double bond and makes it aromatric.
N
In pyridine , lone pair is available as the does not undergo in resonance.
NH2
16. A : on reaction with HNO2 gives CH2 OH as major product.
+ +
R: CH2 carbocation is more stable than carbocation.
+
In CH2 s-character is 17% and is highly stable due to sigma resonance.
Filtrate Residue
+ R
[R N Ph SO2]K
N SO2 Ph
R
70% H2SO4
70% H2SO4
R NH2
R2 NH
1° amine
2° amine
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258 Amines Solutions of Assignment (Set-2)
Zn dust/NaOH/
A. Ph NO2
Ph NH NH Ph
Hydrazobenzene
NO2 NH2
Sn/HCI/
R. (Reduction)
19. A : Coupling reaction is used for the identification of aliphatic primary amine.
R : It is called dye test.
Sol. Answer (4)
1° aime can be identified by treating then with CS2 (Hoffman mustard oil reaction)
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