UNIT-XIII.ORGANIC COMPOUNDS CONTAINING NITROGEN

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1 UIT-XIII.ORGAIC COMPOUDS COTAIIG ITROGE SUB TOPIC I: AMIES ITRODUCTIO 1. Which of the following statements is wrong? I) amines possess pyramidal shape II) Amines act as Bronsted bases III) 1 0 amines show metamerism IV) 2 0 amines show metamerism 1) I, II and III 2) II, III and IV ) III only 4) I, II and IV 2., -dimethyl butanamine-2 contains 1) sixsp hybridised carbon atoms 2) seven sp hybridised atoms ) twosp hybridised nitrogen atoms 4) 1 and 2 are correct. Primary amino group is absent in 1) p-amino phenol 2) o-amino phenol ) -methyl ethanamine 4) phenyl amine 4. A): n-propyl amine is 1 0 but isopropyl amine is 2 0 amine R): n-propyl amine and isopropyl amine are position isomers 1) A and R are true and R explains A 2) A and R are true but R does not explain A ) A is true but R is false 4) A is false and R is true 5., -dimethyl butanamine-2 is the functional isomer of 1) butanamine 2 2) -methyl-2-ethyl butanamine-2 ) trimethyl amine 4) triethyl amine 6. n-butyl amine and isobutyl amine are ---- isomers 1) optical 2) functional ) chain 4) position 7. How many isomers with the molecular formula C 4 H 11. 1) 1 2) 2 ) 4) Represents Primary amine Secondary amine Tertiary amine All of these

2 9. How many primary amines are possible for the formula KEY 1) 4 2) 1 ) 4) 4 5) 4 6) 7) 4 8) 4 9) 4 SUBTOPIC II: ITRO BEZEE 1. itrobenzene HydrazoBenzene. Here the reagent is 1) Sn + HCl 2) Zn + H 4 Cl ) Zn + aoh 4) LiAlH 4 2. In the reaction the equivalent weight of itrobenzene is 1) M 2) M 2 ) M 4 4) M 6. O R O and R-O- = O are a pair of 1) Chain Isomers 2) Metamers ) Functional Isomers 4) Epimers 4. Here the reagent is 1) Zn + H 4 Cl 2) Zn + aoh ) Sn + HCl 4) LiAlH 4

3 O 2 Azobenzene 5. Hydrazobenzene H H The ratio of the number of moles of Hydrogen atoms required to get 1 mole of azobenzene and 1 mole of hydrazobenzene 1) 4 : 5 2) 5 : 4 ) 1 : 1 4) 2 : H SO conc HO C (conc) the main product of the reaction 1) Aniline 2) O dinitrobenzene ) m dinitrobenzene 4) P dinitrobenzene 7. itrobenzene is reduced by Zn and alcoholic KOH 1) C 6 H 5 H 2 2) C 6 H 5 H-H C 6 H 5 ) C 6 H 5 - = - C 6 H 5 4) C 6 H 5 - H - CO - C 6 H 5 8. itro benzene on reduction with Zinc and H 4 Cl gives 1) Azo benzene 2) Aniline ) Hydrazo benzene 4) - Phenyl hydroxyl amine 9. The structure of the compound formed when itrobenzene is reduced by lithium aluminium hydride (Li AlH 4 ) 1) H H HOH 2) H 2 ) 4) =

4 10. itro benzene undergoes reduction with Zn/ alcoholic KOH to from a compound 'A'. The numbers of sigma and Pi bonds in A respectively are 1) 17,6 2) 27,6 ) 27,8 4) 17,8 KEY 1) 2) 4 ) 4) 5) 1 6) 7) 2 8) 4 9) 4 10) 2 SUBTOPIC III: AILIE 1. can react with a maximum of... moles of I 1) 4 2) ) 2 4) 1 2. In the nitration of aniline the amino group is protected by conversion into 1) Tribromo derivative 2) Isocyanide ) Diazonium salt 4) Acetyl derivative. The following turns brown on exposure to air and light 1) itrobenzene 2) m-dinitrobenzene ) Aniline 4) Benzene diazonium chloride 4. In the preparation of -phenyl benzene sulphonamide from aniline, the reagent used is 1) H 2 SO 4 2) SOCl 2 ) C 6 H 5 Cl 4) C 6 H 5 SO 2 Cl

5 5. Which of the following is correct with respect to the order of basic natures of different amines given below? 1) C 6 H 5 H 2 > H > H 2 > ( ) H 2 H> H > C H H > H ( ) 2) H 2 > 2 H > C 6 H 5 H 2 > H ) ( ) H > H > H > C H ( ) 4) Which of the following methods is used to prepare Aniline on large scale? H Fe H O + A) C 6 H 5 O 2 + 6(H) C 6 H 5 H 2 + 2H 2 O B) C 6 H 5 O 2 + 6(H) Sn HCl C 6 H 5 H 2 + 2H 2 O ZnCl 2 C) C 6 H 5 OH 2 +H 00 0 C C 6 H 5 H 2 +H 2 O D) C 6 H 5 Cl + 2H C 6 H 5 H 2 + H 4 Cl 1) A only 2) B or C ) C only 4) A or D 7. Aniline is not the major Product in one of the following reaction. Identify that reaction Zncl2 0 1) C 6 H 5 -OH + H 00 c 2) C 6 H 5 O 2 + Zn Powder alcoholic KOH Cu O high pressure ) C 6 H 5 Cl+ H 2 4) C 6 H 5 O 2 + Fe + H 2 O Hcl

6 8. Which of the following is obtained in a Carbyl amine reaction? 1) C 6 H 5 H 2 2) COCl 2 ) C 6 H 5 C 4) C 6 H 5 C 9. Which of the following reaction can produce aniline as the main product 1) C 6 H 5 O 2 + Zn/KOH 2) C 6 H 5 O 2 + Zn/H 4 Cl ) C 6 H 5 O 2 + Li Al H 4 4) C 6 H 5 O 2 + Zn/HCl 10. Most basic among the following is 1) Benzyl amine 2) aniline ) acetanilide 4) p-nitro aniline 11. Most reactive towards electrophillic substitution is 1) Aniline hydro chloride 2) aniline ) itro benzene 4) -acetyl aniline 12. In-correct statement about aniline is 1) It is less basic than ethyl amine 2) it is steam volatile ) On reaction with a, it gives H 2 4) it is highly soluble in water 1. On reduction, primary amine is formed by 1) 1-nitro ethane 2) ethyl nitrite )azo benzene 4) ethyl carbyl amine 14. Carbyl amine reaction is answered by 1) Methanamine 2) nitro methane ) acetamide 4) trimethyl amine 15. Zwitter ion is formed by 1) Aniline 2) sulphanilic acid ) glycine 4) both 2 and 16. Benzamide can be converted into aniline by the action of 1) Br 2 /CCl 4 2) Br 2 /water ) Br 2 /KOH 4) Br 2 /red P 17. The process that does not yield an amine is 1) action of ammonia on RX 2) reduction of aldoxime with a/alcohol ) acid hydrolysis of alkyl cyanide 4) reduction of amide with LAH 18. Among different aliphatic amines, correct order of basic strengths in vapour state is 1) 0 >2 0 >1 0 2) 1 0 >2 0 > 0 ) 2 0 >1 0 > 0 4) 0 >1 0 > Conversion of a primary amide into a primary amine is called 1) Gabriel s pthalimide reaction 2) Hoffmann bromamide reaction ) Carbyl amine reaction 4) Hinsberg s reaction

7 20. Ethanamine can be obtained from methyl iodide by the action of alc.kc followed by 1) Hydrolysis 2) oxidation ) Reduction 4) action of H /heat 21. The following amide does not undergo Hoffmann s degradation A) Propionamide B) -methyl butanamide C) Butanamide D),-dimethyl butanamide 1) D only 2) C only ) C and D 4) B and D 22. In-correct statement among the following is I) LiAlH 4 can reduce an amide into amine without change in the number of carbon atoms II) a primary amide can be reduced to a primary amine by Br 2 /KOH with same number of Carbon III) a primary amide can be reduced to a primary amine by LiAlH 4 with (n-1) carbon atoms IV) Hoffmann s bromamide reaction is useful to prepare aniline from Benzamide. 1) II only 2) I only ) III and IV 4) II and III 2.,-dimethyl ethanamide on reduction with LiAlH 4 gives 1) -methyl ethanamine 2), -dimethyl ethanamine ) ethanamine 4) trimethyl amine 24. Most reactive towards electrophillic substitution is 1) Aniline hydro chloride 2) aniline ) itro benzene 4) -acetyl aniline 25. On reduction, primary amine is formed by 1) 1-nitro ethane 2) ethyl nitrite ) azo benzene 4) ethyl carbyl amine 26. Butanone oxime on reduction with a/c 2 H 5 OH gives 1) 0 amine 2) 1 0 amine ) 2 0 amine 4) 1 0 amide 27. Which of the following groups will increase basic strength of aniline? 1) -O 2 in ortho or para 2) -O in ortho or para ) -SO H in ortho or para 4) -OH in ortho or para 28. Aniline gives meta derivative as major product with 1) COCl/pyridine 2) HO +H 2 SO 4 ) Br 2 /water 4) Cl/pyridine

8 29. Bromination of aniline in acid medium results as major product 1) 2,4,6-tri bromo aniline 2) -bromo aniline ) 2-bromo aniline 4) 4-bromo aniline 0. Ethyl amine can be distinguished from Aniline by 1) Tollen s reagent 2) Schiff s reagent ) Azo dye test 4) Carbylamine test 1. A mixture of three amines A,B and C is treated with Benzene sulphonyl chloride and filtered. B is obtained in the filtrate. The mixture containing A and C is treated with KOH so that A becomes soluble while C does not. ow, A, B and C are 1) aliphatic primary, secondary and tertiary 2) aliphatic secondary, tertiary and primary ) aliphatic primary, tertiary and secondary 4) aliphatic tertiary, secondary and primary 2. Which of the following on Hoffmann s bromamide reaction gives alkanamine? 1) R 2 H 2 2) RCOHR ) RCOH 2 4) RCOOH 4. Dye test is used to distinguish 1) ethanamine and methanamine 2) methanamine and propanamine-1 ) benzenamine and ethanamine 4) urea and acetanilide 4. Aniline is 1) More basic than ammonia 2) more basic than p-amino phenol ) More basic than p-nitro aniline 4) as basic as methyl amine 5. Acetanilide on nitration followed by hydrolysis yields --- as main product. 1) 4-nitro aniline 2) 2,4,6-trinitro aniline ) 2-nitro aniline 4) -nitro aniline 6. Among the following, strongest base is 1) aniline 2) p-nitro aniline ) m-nitro aniline 4) benzyl amine 7. The compound which on reaction with aqueous nitrous acid at low temperature produces in oily nitrosamine is Methylamine Ethylamine Diethylamine Triethylamine 8. Acetamide is treated separately with the following reagents. Which one of these would give methylamine? PCl 5 Sodalime aoh+br 2 hot concentrated H 2 SO 4

9 9. Carbylamine test is performed in alcoholic KOH by heating a mixture of Chloroform and silver powder Trihalogenated methane and a primaryamine An alkyl halide and a primart amine. An alkyl cyanide and a primary amine. 40. Chlorobenzene can be prepared by reacting aniline with Hydrochloric acid Cuprous chloride Chlorine in the presence of anhydrous aluminium chloride. itrous acid followed by heating with cuprous chloride. 41. Amongst the following, the most basic compound is Benzylamine aniline Acetanilide p-nitroaniline 42. Reaction of RCOH 2 with a mixture of Br 2 and KOH gives RH 2 as the main product. The intermediates involved in the reaction are O R C HBr R HBr R C O R C Br Br 4. Examine the following two structures for the anilinium ion and chose the correct statement from the ones gives below. + H H II is not acceptable canonical structure because carbonium ions less stable than ammonium ions II is not an acceptable canonical structure becasue it is nonaromatic II is not an acceptable canonical structure because nitrogen has 10 valence electrons II is an acceptable canonical structure

10 44. Which of the following statement is not correct? Replacement of halogen by H 2 in alkyl halide is a nucleophilic substitution reaction Aryl halides show more reactivity as compared to alkyl halides in the replacements of halogen by H 2 group During the replacement of halogen by H 2 group, ammonia is taken in large excess so as to avoid the formation of 2 0 and 0 amines. Tertiary alkyl halide generally produces alkene instead of the replacement of halogen by H 2 group. 45. Which of the following statements is not correct? Primary amines show intermolecular hydrogen bonding Secondary amines shows intermolecular hydrogen bonding. Tertiary amines show intermolecular hydrogen bonding. Amines have lower boiling points as compared to those of alcohols and carboxylic acids of comparable. 46. Which of the following statements is not correct? Aliphatic amines are stronger bases than ammonia. Aromatic amines are stronger bases than ammonia The alkyl group in alkyl ammonium ion more stabilizes the ion relative to the amine The aryl group in aryl ammonium ion less stabilizes the ion relative to the amine. 47. Hinsberg s reagent is Phenylisocyanide p-toluenesulphonic acid Benzenesulphonyl chloride O-dichlorobenzene 48. On warming an aqueous solution of benzenediazonium chloride, the product obtained is Benzene Aniline Phenol amide 49. Which of the following reagents can convert benzenediazonium chloride into benzene? Water Acid Hypophosphorous acid HCl 50. Hofmann s method to separate amines in a mixture uses the reagent? Benzenesulphonyl chloride Benzeneisocyanide Diethyl oxalate P-toluenesulphonic acid

11 51. Which of the following compounds will dissolve in an alkali solution after it has undergone reaction with Hinsberg reagent? (C 2H 5) 2H H2 C H 6 5 H Activation of benzene ring by-h 2 in aniline can be reduced by treating with Dilute HCl Ethyl alcohol Acetic acid Acetyl chloride 5. Which of the following orders is correct regarding the basic strength of substituted aniline P- nitroaniline> P-aminobenzaldehyde> P-bromoaniline P-nitroaniline<P-bromoaniline< P- aminobenzaldehyde P- itroaniline< P - aminobenzaldehyde< P - bromoaniline P - itroaniline>p - aminobenzaldehyde< P - bromoaniline 54. Which of the following orders regarding the basic strength of substituted aniline is correct? P-methylaniline> P-chloroaniline> P- aminoacetophenone P-methylaniline P- aminoacetophenone> P- chloroaniline P-aminoacetophenone>P-methylaniline> P - chloroaniline P-aminoacetophenone>P-chloroaniline> P- methylaniline 55. The number of resonating structures of arylammonium ion is The number of resonating structures of aniline is The bromination of aniline produces 2- bromoaniline 2, 4, 6-tribromoaniline 4-bromoaniline 2, 6-dibromoaniline 58. A positive carbylamine test is given by, -dimethylaniline -methyl1-o-methylaniline 2, 4-dimethylaniline P- methylbenzylamine

12 59. Among the following, the strongest base is H m O C H H P O C H H H Identify the product C in the given reaction. a/c H OH HO Cu/ C C A B C COOH COH 2 2 H OH = O H 61. What is the product when reacts with nitrous acid? OH H Which of the following is activating group for nitration reaction? O O C O C O O C R C - = O 6. Which of the following having highest value of K b? H 6 5 COH 2 H H Strongest base among the following is H 2 H 65. Identify the product C in the given reaction ( ) ( ) a/c2h5oh HO Cal/00 C C A B C - COOH - COH H - OH - = O

13 66. Column - I Column - II (A) itrobenzene Azobenzene (P) LiAIH4 (B) Aniline Phenylisocyanide (Q) ao2 + HCl+Cu 2 Cl 2 (C) Aniline Chlorobenzene (D) Ethylamine Ethanol (R) Cl +KOH (S) ao 2 + HCl (aq) A B C D 1) P Q R S 2) P R Q S ) S R Q P 4) P R S Q 67. Which amine is heated with chloroform and alcoholic KOH, a bad odour compound is formed. The compound is An alcohol An aldehyde A cyanide An isocyanide 68. The molecular formula of methyl isocyanate is CO CO CS C 69. The product of the reaction of the alcoholic silver nitrite with ethyl bromide is Ethene Ethyl nitrite Ethyl alcohol itroethane LiAlH 70. Which one of the following on reduction with 4 yields a secondary amine Methyl cyanide itroethane Methyl isocyanide Acetamide 71. When methyl cyanide is hydrolysed in presence of alkali, it forms CO Acetamide Methane 2 + H2O Acetic acid 72. Acetamide reacts with aobr in alkaline medium to form H H2 C 2H2 7. Treatment of ammonia with excess of ethyl chloride will yield Diethylamine Tetraethyl ammonium chloride Methylamine Ethane

14 74. The correct order of the increasing basicity of methylamine, ammonia and aniline is Methylamine < aniline < ammonia Aniline < methylamine < ammonia Methylamine < ammonia < aniline Aniline < ammonia < methylamine 75. H 2 +Cl + KOH X + Y + H 2 O ; compounds X and Y are C + KCl COH2 + KCl 76. In the following series of reactions, (A) is C + KCl C + K CO 2 ( A)Re duction( B) HO2C2H 5OH C C C 2 5 O2 ac i/ H2 Acetic anhydride Cl ( X ) ( Y ) ( Z) (Z) in the above reaction sequence is 2 2HCO 2 2COH 22H2 22COHCO 78. A primary amine is formed from an amide, by the treatment of bromine and alkali. The primary amine has 1 carbon atom less than amide 1 hydrogen atom less than amide 1 carbon atom more than amide 1 hydrogen atom more than amide 79. Acetonitrile on reduction gives Propanamine Methanamine Ethanamine one of these 80. An isonitrile on reduction gives amine amine amine Quaternary ammonium salts 81. Ethyl chloride on heating with AgC forms a compound (X). The functional isomer of (X) is C 2 5 H C 2 5 one of these 82. The reduction of which of the following compound would yield secondary amine Alkyl nitrile Primary amine Carbylamine Secondary nitro compound

15 H + Cl + KOH nitrogen HO containing compound + KCl+ 2. itrogen containing compound is 8. 2 C C + H + C KEY 1) 2) 4 ) 4) 4 5) 4 6) 1 7) 2 8) 4 9) 4 10) 1 11) 2 12) 4 1) 1 14) 1 15) 4 16) 17) 18) 1 19) 2 20) 21) 4 22) 4 2) 2 24) 2 25) 1 26) 2 27) 4 28) 2 29) 2 0) 1) 2) ) 4) 5) 1 6) 4 7) 8) 9) 2 40) 4 41) 1 42) 1 4) 44) 2 45) 46) 2 47) 2 48) 49) 50) 2 51) 52) 4 5) 54) 1 55) 1 56) 4 57) 58) 4 59) 4 60) 4 61) 62) 2 6) 4 64) 65) 4 66) 2 67) 4 68) 1 69) 4 70) 71) 4 72) 2 7) 74) 4 75) 2 76) 1 77) 1 78) 1 79) 80) 2 81) 82) 2 8) 4

16 SUBTOPIC IV: DIAZOIUM SALTS 1. Benzene diazonium chloride on reaction with KC in the presence of CuC yields X. X on hydrolysis yields Y. ow, Y can also be obtained from 1) Toluene by the action of Cl 2 /FeCl 2) Toluene by oxidation by KMnO 4 ) Toluene by nitration 4) Toluene by sulphonation 2. dil. H 2SO4 Ar. 2Cl X HCl where regarding X, correct statement is 1) it is weakly acidic 2) it liberates H 2 with a ) it is stronger acid than acetic acid 4) 1 and 2. Benzene diazonium salt on reduction with X yields Benzene. X is 1) K 2 Cr 2 O 7 /H + 2) O ) H PO 4 4) H PO 2 4. A):Diazonium ion acts as an electrophile R): Terminal nitrogen atom in diazo group is positively charged 1) A and R are true and R explains A 2) A and R are true but R does not explain A ) A is true but R is false 4) A is false but R is true 5. During diazo coupling, the following group is retained 1) = 2) 2 Cl ) H 2 4) HR 6. Which of the following is an example of electrophillic substitution? 1) diazotisation 2) Sandmayer reaction ) diazo coupling 4) action of KC on Ar 2 Cl 7. Which of the following is the correct order of ease of coupling with C 6 H 5 2 Cl? A) Benzene B) itro benzene C) Phenol D) Chloro benzene 1) A > D > B > C 2) C > A > B > D ) C > A > D > B 4) B > D > A > C 8. Coupling of phenol with benzene diazonium salt yields 1) o-hydroxy derivative of salt 2) p-hydroxy derivative of salt ) m-hydroxy derivative of salt 4) a mixture 1, 2 and 9., -dimethyl aniline on coupling with C 6 H 5 2 Cl yields 1) 4-(,-dimethyl) amino azo benzene 2) 4-(,-dimethyl) nitroso benzene ) 4-(,-dimethyl) amino azoxy benzene 4) 4-(,-dimethyl) amino hydrazo benzene

17 10. Which of the following reactions is an example of Sandmeyer reaction? + 2 HSO4 Br + 2 HSO4 Br CuBr Cu powder HBr + 2 HSO4 I + 2 HSO4 C KI CuC 11. Which of the following reaction is an example ofgattermann reaction? + 2 HSO4 Br + 2 HSO4 Br CuBr Cu powder HBr + 2 HSO4 C + 2 HSO4 I CuC KI 12. Benzenediazonium chloride on reaction with phenol in weakly basic medium gives Diphenyl ether Chlorobenzene P- hydroxyazobenzene Benzene 1. Which of the following is responsible for the colour of diazocompounds? Benzene ring - = -group -OH group -H 2 group 14. Coupling between arenediazoniumcation and amines takes place most rapidly at ph

18 Cl + O A A is = O O OH OH KEY 1)2 2) 4 ) 4 4) 5) 1 6) 7) 8) 2 9) 1 10) 1 11) 2 12) 2 1) 2 14) 15) 2

Benzylamine reacts with nitrous acid to form unstable diazonium salt, which in turn gives alcohol with the evolution of nitrogen gas.

Benzylamine reacts with nitrous acid to form unstable diazonium salt, which in turn gives alcohol with the evolution of nitrogen gas. On the other hand, aniline reacts with HNO2 at a low temperature to