2021 Exam

1. Nitration of the following heterocycle(s) occurs majorly at position 2

a) Indole.
b) Furan and benzofuran.
c) Thiophene and benzo[b]thiophene.
d) Pyridine and quinoline.

2. Nucleophile can attack ………… at position 2

a) Quinoline.
b) Pyrimidine
c) Pyridine
d) All of the above.

3. Which pyridine derivative is more reactive than pyridine towards both nitration and
Chichibabin reactions?

a) Pyridine-N-oxide
b) Pyridinium methiodide.
c) 2-Aminopyridine.
d) 2-Chloropyridine.

4. The final product obtained from the following reactions is….

Butane-2,3-dione+ ethylenediamine  ? , then oxidation  final product.

a) b) c) d)

5. Which of the following reactions shows wrong product ?

a) Pyridine-N-oxide + POCl3  2,4-dichlopyridine.

b) Pyridine + methyl iodide  ? 2-methylpyridine.
c) Pyridine-N-oxide + PCl3  pyridine.
d) None of the above.
* Nifedipine, sold under the brand name Adalat ®, is a medication used to manage high blood
pressure. This drug is easily transformed to the corresponding fully aromatic biologically
inactive derivative. Given this information, answer questions 6-10.

6. Nifedipine is transformed to the aromatic derivative by….

a) oxidation.
b) reduction.
c) neutralization.
d) electrophilic substitution.
7. The aromatic inactive product is….

a) acidic.
b) basic.
c) neutral.

8. Nifedipine can be prepared by the reaction of….

a) aldehyde, amine and ketoester.

b) ketone, amine and ester.
c) aminoketone and ketoester.
d) aminoketone, aldehyde and ester.

9. You can confirm the convertion of nifedipine to the aromatic inactive derivative if you
compare the 1H NMR charts of pure nifedipine and the inactive aromatic product. Which of the
following observations is an evidence for such transformation?

a) The D2O exchangeable peak in the 1H NMR chart of pure nifedipine will disappear in the
1
H NMR chart of the inactive aromatic derivative.
b) A new D2O exchangeable peak will appear in the the 1H NMR chart of the inactive
aromatic derivative.
c) The 1H NMR chart of the aromatic derivative shows new peak at the aliphatic region.
d) The 1H NMR chart of the aromatic derivative shows new peak at the aromatic region.

10. Do you think that IR can guide you to confirm the transformation if you don’t have access to
NMR?

a) Yes, through the disappearance of absorption band at 3200 cm-1.

b) Yes, through the disappearance of absorption bands at 1600-1700 cm-1 .
c) Yes, through the appearance of new absorption bands at 3200 cm-1 .
d) No, no change can be detected after aromatization.

11. Thiophenoxyacetic acid reacts with phosphorous pentoxide to produce….

 a) 2-hydroxybenzo[b]thiophene.
b) 2-hydroxybenzo[c]thiophene.
c) 3-hydroxybenzo[b]thiophene.
d) 3-hydroxybenzo[c]thiophene.

12. o-Phthalaldehyde reacts with hydrazine to produce….

a) benzo[b]pyridazine.
b) benzo[b]pyrimidine
c) benzo[d]pyridazine.
d) benzo[d]pyrimidine.

13. Hex-3-ene-2,5-dione reacts with hydrazine to produce….

a) 1,4-dimethylpyrazine
b) 1,4-dimethylpyridazine.
c) 3,6-dimethylpyriazine.
d) 3,6-dimethylpyridazine.

14. 3-Chloropyridine is prepared by.…

a) reaction of pyridine with Cl2 gas.

b) Reaction of pyridine with Sandmayer’s reagents.
c) reaction of pyrrole with CHCl3 / KOH.
d) Chichibabin’s reaction.

15. Pyridine reacts with HBr to produce….

a) pyridinium hydrobromide.
b) 3-bromopyridine.
c) 3,5-dibrompyridine.
d) Nothing; no reaction occurs.

16. Pyridine reacts with KNO3 / H2SO4 / 370oC to produce….

a) pyridinium hydrogen sulphate.

b) 3-nitropyridinium hydrogen sulphate.
c) 4-nitropyridine.
d) pyridine-3-sulphonic acid.

17. Butandial reacts with phosphorous pentasulphide, then with N-bromosuccinimide to finally
produce….
 a) thiophene.
b) 2-bromothiophene.
c) 5-bromothiophene.
d) 2,5-dibromothiophene.
18. 1,3-Diazole….

a) is called pyrazole.
b) undergoes tautomerism.
c) its molecular formula is C3H3N2
d) is as basic as pyridine.

19. Phenethylamine reacts with acetylchloride, then phosphorous oxychloride to produce….

a) 1-methylisoquinoline.
b) 2-methylquinoline.
c) 1-methyl-3,4-dihydroisoquinoline.
d) 2-methyl-3,4-dihydroquinoline.

20. 4-Aminopyridine is best prepared by….

a) Chichibabin’s reaction of pyridine.

b) nitration, then reduction of pyridine.
c) nitration, then reduction of pyridine-N-oxide.
d) heating pyridine and ammonia.

21. 2-Pyridone is prepared by….

a) boiling pyridine-2-diazonium salt in water.

b) heating 2-chloropyridine and potassium hydroxide.
c) all of the above.
d) none of the above.

22. 2-Aminopyridine is prepared by….

a) Chichibabin’s reaction of pyridine.

b) heating 2-chloropyridine and sodamide.
c) reaction of pyridine-2-diazonium salt with ammonia.
d) all of the above.

23. Piperidine is….

a) the oxidation product of pyridine.

b) the reduction product of pyridine.
 c) basic aromatic heterocycle.
d) acidic aromatic heterocycle.

24. Imidazole reacts with methyliodide to produce….

a) N-methylimidazole.
b) 4(5)-methylimidazole.
c) 4-methylimidazole.
d) 5-methylimidazole.

25. Pyrrole-2-carboxylic acid is prepared by reacting pyrrole with….

a) CHCl3 / NaOH.
b) CH3Cl / NaOH.
c) CO2 / NaOH.
d) HCOOH / NaOH.

26. Heating aminacetone and acetone in presence of acidic catalyst produce….

a) 2,3-dimethylpyrrole.
b) 2,4-dimethylpyrrole.
c) 2,5-dimethylpyrrole.
d) N-methylpyrrole.

27. The correct nomenclature of the following compound is.…

a) 3-aminoethyl-5-hydroxy indole.
b) 3-aminoethyl 5-hydroxy benzo[b]indole.
c) 1-aminoethyl 6-hydroxy indole.
d) 1-aminoethyl 6-hydroxy benzo[2,3-b]indole.

28. The IUPAC is….

a) a pharmaceutical company.
b) The commercial nomenclature system of organic compounds.
c) an international organization.
d) an important organic chemistry textbook.

29. A heterocyclic compound….

a) should be aromatic.
b) can’t form salt.
c) may be aliphatic or aromatic.
 d) None of the above.

30. The correct nomenclature of the following compound is….

a) pyrimido[4,5-c]pyridazine.
b) pyrazino[4,5-c]pyridazine.
c) Pyridazino[3,4-d]pyrimidine.
d) Pyridazino[4,5-c]pyrimidine.

31. The correct nomenclature of the following compound is….

a) 8H-pyrido[3,2-d]-1,2-oxazine.
b) 8H-pyrido[2,3-d]-1,2-oxazine.
c) 5H-pyrido[3,2-d]-1,2-oxazine.
d) 5H-pyrido[2,3-d]-1,2-oxazine.

32. The correct nomenclature of the following compound is….

a) thiazolo[2,1-b]imidazole.
b) imidazo[2,1-b]thiazole.
c) thieno[2,3-b]imidazole.
d) pyrrolo[2,3-b]thiazole.

33. The correct nomenclature of the following compound is….

a) 4-methyl imidazole-2-carboxaylic acid.

b) 5-methyl imidazole-2-carboxaylic acid.
c) 4(5)-methyl imidazole-2-carboxaylic acid.
d) 3-methyl imidazole-1-carboxaylic acid.

* Guided by the following scheme , answer questions 34-36

34. If the product P1 is quinoline, the reagent R1 is….

a) acrolein and sulfuric acid.

b) glycerol and sulfuric acid.
c) acrolein and arsenic pentoxide.
d) glycerol and arsenic pentoxide.

35. If the product P2 is pyridine-3-carboxylic acid, then the reagent R2 is….

a) oxidizing agent.
b) reducing agent.
c) Lewis acid.
 d) Grignard reagent.

36. If the reagent R3 results from reacting α-aminoacetone and acetyl chloride, then the product
P3 is….
a) 1-phenyl-2,5-dimethylpyrazole.
b) 1-phenyl-2,5-dimethylimidazole.
c) 3-phenyl-1,5-dimethylpyrazole.
d) 2-phenyl-1,5-dimethylimidazole.

37. Imidazole….

a) can form salt with acid.

b) can form salt with base.
c) can form salt with acid or base.
d) can’t form salts.

38. Which statement is wrong?

a) Aniline is more basic than pyridine.

b) Pyridine is more basic than aniline.
c) Imidazole is more basic than pyridine.
d) Imidazole is more basic than aniline.
39. Which statement is wrong?

a) Furan is less reactive than thiophene.

b) Thiophene is less reactive than furan.
c) Furan is more reactive than pyrrole.
d) Benzene is more stable than pyrrole.

40. Which statement is correct ?

a) A nuclreophile donates electrons.

b) A nucleophile accepts electrons.
c) The mixture of conc. nitric and suphuric acids is a source of strong nucleophile.
d) None of the above.

* Guided by the next scheme answer questions 41-44

41. If the reagent R1 is pyruvic acid, the product P1 is….

a) a heterocyclic compound.
b) a hydrazone.
c) a hydrazide.
 d) None of the above.

42. If the reagent R2 is ZnCl2 (with heating), then the product P2 is….

a) a hydrazone.
b) an acid.
c) a heterocyclic compound.
d) None of the above.

43. If the reagent R3 is acetyl nitrate, then the reaction of P2 with R3 to produce P3 is….

a) an electrophilic substitution reaction.

b) a nucleophilic substitution reaction.
c) oxidation.
d) reduction.

44. If the reagent R4 is benzoyl acetone, then the product P4 is….

a) 3-methyl-1,5-diphenylpyrazole.
b) 1,5-diphenylpyrazole.
c) 3,5-diphenylpyrazole.
d) 4-methyl-1,2-diphenylimidazole.

45. Hydrazine reacts with o-phthaladehyde to produce….

a) phthalazine.
b) bicyclic compound.
c) Benzo[d]pyridazine.
d) All of the above.
46. Pyrazole is the product of reacting hydrazine with….

a) malondialdehyde.
b) acetic acid.
c) acetaldehyde.
d) none of the above.

47. Pyrazole reacts with oleum at 100 oC to produce….

a) pyrazole-3-sulfonic acid.
b) pyrazole-4-sulfonic acid.
c) 3-nitropyrazole.
d) 4-nitropyrazole.
48. Thiourea reacts with ……….. to produce 4,6-dimethylpyrimidine-2(1H)-thione.

a) pentan-2,4-dione.
b) hexan-2,5-dione.
c) acetone.
d) butanedial.

49. Peracetic acid is useful for preparing….

a) pyridine-N-oxide.
b) Benzofuran.
c) benzothiophene.
d) (b) and (c).

50. Sodamide is useful in….

a) Chichibabin reaction.
b) Reimer-Tiemann reactio.
c) Friedel Craft’s acylation.
d) Friedel Craft’s alkylation.