Aromaticity in benzenoid and non‑benzenoid systems and related reactions - Question Bank
1. Which of the following is an example of a non-benzenoid aromatic heterocyclic compound?
2. The Birch reduction of benzene leads to:
3. Which of the following is a characteristic of heteroaromatic compounds like furan or thiophene?
4. The reaction of benzene with a diazonium salt in the presence of a base is known as:
5. Which statement about aromaticity is FALSE?
6. The Wheland intermediate (arenium ion) in electrophilic aromatic substitution is:
7. Which of the following would be the most deactivated towards electrophilic aromatic substitution?
8. The stability of benzene compared to hypothetical hypothetical cyclohexatriene is quantified by its:
9. Which of the following is an example of a fused polycyclic aromatic hydrocarbon (PAH)?
10. Which of the following is a common reaction used to remove a sulfonic acid group from a benzene ring?
11. A compound that is cyclic, planar, and has delocalized pi electrons, but does not follow Hückel's rule (e.g., 8 pi electrons) would be classified as:
12. The regioselectivity of electrophilic aromatic substitution on monosubstituted benzenes is determined by:
13. Which type of catalyst is typically used in the halogenation of benzene?
14. In pyridine, the nitrogen atom contributes to aromaticity by:
15. The compound pyridine is considered aromatic because:
16. Which of the following is a characteristic of antiaromatic compounds?
17. The resonance energy of aromatic compounds is:
18. Which of the following is an example of a non-aromatic compound?
19. A compound that is planar, cyclic, has 4n pi electrons, and is expected to be unstable compared to benzene is called:
20. What is the primary driving force for the stability of aromatic compounds?
21. Friedel-Crafts acylation is often preferred over alkylation because:
22. Which reaction involves the introduction of an acyl group (-COR) onto the benzene ring?
23. A compound that has the same number of pi electrons as benzene (6 pi electrons) but is not a benzene derivative is:
24. Which of the following is an example of a fused ring aromatic system?
25. The order of reactivity of benzene and its derivatives towards electrophilic substitution, with deactivating groups, is generally:
26. The order of reactivity of benzene and its derivatives towards electrophilic substitution, with activating groups, is generally:
27. Which reaction is used to introduce a halogen onto the benzene ring?
28. Friedel-Crafts alkylation is generally not preferred for introducing secondary or tertiary alkyl groups because of:
29. Sulfonation of benzene can be reversed by treatment with:
30. Nitration of benzene typically uses a mixture of concentrated nitric acid and:
31. Halogens (-Cl, -Br, -I) are deactivating but ortho, para directors in electrophilic aromatic substitution due to:
32. Which functional group is typically activating towards electrophilic aromatic substitution and is an ortho, para director?
33. Which functional group is typically deactivating towards electrophilic aromatic substitution?
34. The intermediate formed during electrophilic aromatic substitution is called:
35. In electrophilic aromatic substitution, the electrophile attacks:
36. Which Lewis acid is commonly used as a catalyst in Friedel-Crafts alkylation?
37. The cyclopentadienyl anion (C5H5-) is aromatic because it has:
38. What is the name of the bicyclic aromatic hydrocarbon with 10 pi electrons?
39. Which of the following is NOT a characteristic of aromatic compounds?
40. The delocalization of pi electrons in aromatic systems leads to:
41. Which of the following conditions is essential for a cyclic compound to exhibit aromaticity?
42. What is the characteristic reaction of aromatic compounds?
43. Cyclooctatetraene is considered antiaromatic because it has:
44. The tropylium cation (C7H7+) is aromatic because it has:
45. What is the number of pi electrons in benzene?
46. Which of the following is an example of a non-benzenoid aromatic compound?
47. Which of the following is an example of a benzenoid aromatic compound?
48. According to Hückel's Rule, an aromatic system must have how many pi electrons?
49. Which rule dictates the number of pi electrons required for aromaticity?
50. What is the primary criterion for a compound to be aromatic?