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This document contains 17 multiple choice questions testing knowledge of heterocyclic aromatic compounds including pyrrole, furan, thiophene, pyridine and related derivatives. Key points addressed include aromatic character, reactivity towards electrophiles, substitution patterns, tautomerism and reaction types such as nitration, oxidation and nucleophilic substitution.
This document contains 17 multiple choice questions testing knowledge of heterocyclic aromatic compounds including pyrrole, furan, thiophene, pyridine and related derivatives. Key points addressed include aromatic character, reactivity towards electrophiles, substitution patterns, tautomerism and reaction types such as nitration, oxidation and nucleophilic substitution.
This document contains 17 multiple choice questions testing knowledge of heterocyclic aromatic compounds including pyrrole, furan, thiophene, pyridine and related derivatives. Key points addressed include aromatic character, reactivity towards electrophiles, substitution patterns, tautomerism and reaction types such as nitration, oxidation and nucleophilic substitution.
b. Pyridine is isoelectronic with benzene. c. Pyrrole has less aromatic character than furan. d. Pyridine is a tertiary amin 2. Which of the following solvents is a heterocyclic compound? a. Diglyme. b. THF. c. DMSO. d. DMF. 3. In pyrrole and pyridine, the number of electrons that the N atom contributes to the π-system is a. pyrrole, 1; pyridine 1. b. pyrrole, 2; pyridine 1. c. pyrrole, 2; pyridine 2. d. pyrrole, 1; pyridine 2. 4. What is the correct order of reactivity (most reactive first) of pyrrole, furan and thiophene towards electrophiles? a. thiophene > pyrrole > furan b. furan > pyrrole > thiophene c. furan > thiophene > pyrrole d. pyrrole > furan > thiophene 5. Electrophilic substitution in furan usually occurs at: a. the C(2) atom. b. the O atom. c. both the C(2) and C(3) atoms. d. the C(3) atom. 6. Nitration of pyrrole is best carried out using a. acetyl nitrate. b. concentrated nitric and sulfuric acids. c. nitric acid. d. ammonium nitrate 7. If you wanted to carry out an electrophilic substitution in pyridine, an initial step could be to react pyridine with H2O2 in acetic acid. What happens in this step? a. 1,4-Dihydropyridine is formed. b. 2-Pyridone is formed. c. 2-Hydroxypyridine is formed. d. Pyridine-N-oxide is formed 8. The reaction of 4-chloropyridine with sodium ethoxide is an example of a. nucleophilic substitution. b. addition. c. addition and elimination. d. electrophilic substitution. 9. Which statement below is incorrect? a. Pyrimidine and pyrazine are isomers. b. In imidazole, each N atom contributes one electron to the π- system. c. Pyrazine is a diazine. d. 4-Methylimidazole and 5-methylimidazole are tautomers 10. If you wanted to form 2,3,4,5-tetrabromopyrrole from pyrrole, which of the following conditions would be the best choice? a. Br2 in the presence of a radical initiator. b. HBr at 298 K. c. Br2 with AlBr3 as a Lewis catalyst. d. Br2 at 273 K 11. Compare the relative reactivities of benzene and pyridine towards electrophiles. Which statement is correct? a. Pyridine is less reactive towards electrophiles than benzene. b. Both pyridine and benzene undergo reactions with electrophiles, but pyridine always forms N-derivatives. c. Both pyridine and benzene behave similarly towards electrophiles. d. Pyridine is more reactive towards electrophiles than benzene 12. Which reagent would you use to convert 2-pyridone to 2- chloropyridine a. PCl3 b. POCl3 c. CCl4 d. HCl 13. 1-Iodobutane reacts with pyridine to give: a. 2-butylpyridine. b. N-butylpyridinium iodide. c. pyridinium iodide. d. 2-iodopyridine. 14. Which statement below is correct? a. Pyrrole readily protonates on the N atom. b. The pKa of the conjugate acid of pyrrole ≈ 7. c. Pyrrole is a very weak base. d. Pyrrole is a stronger base than triethylamine 15. Nitration of furan using acetyl nitrate also leads to a 2,5-addition product. How can this competing process be suppressed? a. By carrying out the nitration in the presence of pyridine. b. By using concentrated nitric and sulfuric acids instead of acetyl nitrate. c. By using nitric acid instead of acetyl nitrate. d. By carrying out the reaction at higher temperatures 16. Which statement about thiophene is incorrect a. Thiophene is more reactive towards electrophiles than furan. b. Thiophene is polar. c. Oxidative polymerization of thiophene leads to a conducting polymer. d. The S atom contributes two electrons to the π-system. 17. Histamine is a derivative of: a. pyridine. b. pyrrole. c. purine. d. imidazole. 18. Which of the following statements is incorrect about the reaction of [Ph3C][BF4] with 4H-pyran? a. A tetrafluoridoborate salt is formed. b. [Ph3C]+ abstracts H– from 4H-pyran. c. An aromatic ring is formed. d. Pyridine is formed