Title: CHE2FND_Aromatic_Quiz

Q: The pK_a of 2,4,6-trichlorophenol is 6.00, while the pK_a of 2,4,6-trinitrophenol is 0.38. By approxiamately what factor is the trinitrophenol more acidic than the trichlorophenol?
- 100,000
- 10,000
- 1,000,000
- 1000
A: 100,000

Q: A chemist was attempting to brominate the aromatic starting material shown below:

[Image: Arom_question9x]

What would be the major product obtained from this reaction?
- [Image: Arom_question9d]
- [Image: Arom_question9c]
- [Image: Arom_question9b]
- [Image: Arom_question9a]
A: [Image: Arom_question9d]

Q: Which substituent below is inductively withdrawing, resonance withdrawing and deactivating?
- -CH_2CH_3
- -NO_2
- -OH
- -Br
A: -NO_2

Q: Of the structures represented below, only one is aromatic. Which one?
- [Image: Arom_question3d]
- [Image: Arom_question3c]
- [Image: Arom_question3b]
- [Image: Arom_question3a]
A: [Image: Arom_question3a]

Q: A pharmaceutical company was looking to synthesize the trisubstituted benzene ring shown below:

[Image: Arom_question10]

Which order of reactions would provide the most efficient synthesis of this compound?
- Chlorination, nitration, then acylation
- Acylation, nitration, then chlorination
- Nitration, chlorination, then acylation
- Chlorination, acylation, then nitration
A: Chlorination, acylation, then nitration

Q: In the presence of a strong base, deprotonation of the aromatic alcohol: [Image: Arom_question4x]produces an aromatic ion. Of the 4 ionised structures represented below, which is NOT a correct resonance form of the aromatic ion?
- [Image: Arom_question4d]
- [Image: Arom_question4c]
- [Image: Arom_question4a]
- [Image: Arom_question4b]
A: [Image: Arom_question4d]

Q: If you added concentrated nitric acid and concentrated sulfuric acid to benzene at low temperature (<5^oC), what product would you expect to obtain?
- [Image: Arom_question7a]
- [Image: Arom_question7d]
- [Image: Arom_question7c]
- [Image: Arom_question7b]
A: [Image: Arom_question7c]

Q: Of the 4 substituted benzoic acids shown below, which would be expected to be the most acidic?
- [Image: Arom_question6d]
- [Image: Arom_question6c]
- [Image: Arom_question6b]
- [Image: Arom_question6a]
A: [Image: Arom_question6b]

Q: What substituent effects would you expect a fluoro substituent (-F) to have?
- Inductively donating, resonance withdrawing, activating
- Inductively withdrawing, resonance withdrawing, deactivating
- Inductively donating, resonance donating, activating
- Inductively withdrawing, resonance donating, deactivating
A: Inductively withdrawing, resonance donating, deactivating

Q: An alkylation reaction was conducted under the conditions as shown below:

[Image: Arom_question8x]

From this reaction, what would be the expected product obtained?
- [Image: Arom_question8d]
- [Image: Arom_question8c]
- [Image: Arom_question8b]
- [Image: Arom_question8a]
A: [Image: Arom_question8d]