UDBB 1164 Fundamentals of Organic ChemistryTutorial 3: Aromatic compounds

1. What is the major organic product obtained from the following reaction?

2. Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?a. benzeneb. nitrobenzenec. bromobenzened. benzaldehyde

3. Which of the following undergoes the most rapid acylation upon treatment with acetyl chloride and AlCl3?a. benzeneb. toluenec. chlorobenzened. 1,4-dichlorobenzene

4. Which of the following sets of substituents are all o/p-directing in electrophilic aromatic substitution reactions?a. Cl, CH3, CNb. Br, OH, COCH3

c. Cl, OH, CH3

d. CN, NO2, COCH3

5. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?a. Cl, CN, NO2

b. Cl, NH2, CH3

c. CH3, OCH3, COCH3

d. CH3, NH2, OCH3

6. What is the major organic product obtained from the following reaction?

7. Place the following in order of reactivity towards electrophilic aromatic substitution.

a. I > II > III > IVb. I > II > IV > IIIc. II > I > III > IVd. II > I > IV > IIIe. III > IV > II > I

8. Consider the production of 1-bromo-4-nitrobenzene:

a) Explain why Pathway A for the production of 1-bromo-4-nitrobenzene produces a higher

yield of the product.

b) If reaction Pathway A is carried out at high temperatures, a trisubstituted product forms. Draw the structure of the product and explain why it forms.

9. Consider the following sequence of reactions:

a) What is the major organic product obtained from the sequence of reactions?

a. b. c. d.

b) If KMnO4 had been replaced by Na2Cr2O7, what would be the final product of the reaction?

10. Consider the following compound:

a) Provide the correct IUPAC name for the compound.

b) Draw and name the other isomeric nitrotoluenes.

11. Which of the following heterocycles is aromatic?a.

b.

c.

d.

12. Draw the structure of o-hydroxybenzoic acid.

13. Draw the structure of 3,5-dimethylphenol.

14.. Draw the structure of p-chlorobenzaldehyde.

Provide the IUPAC name for each of the following compounds.

15. IUPAC Name:

16. IUPAC Name:

17. IUPAC Name:

18. IUPAC Name:

19. Consider the Friedel-Crafts alkylation reaction below to answer the following questions:

On the structures provided below, draw arrows showing the complete stepwise mechanism for this reaction.

20. Write the product:

21. Write the product:

22. Write the product:

23. Write the product:

24. Write the product:

25. Write the product:

26. Write the product:

27. What reagents are required for:

28. What reagents are required for:

29. Synthesize from benzene:

29. Synthesize from toluene:

30. Synthesize from benzene: