Name______________________________________________________________

SN______

Multiple Choice. Identify the choice that best completes the statement or answers the question. ____ 1. What is the IUPAC name of the following compound?

a. 2,4-dibromotoluene ____

b. 2,4-dibromophenol dibromophenol

c. 2,4-dibromoaniline

d. 4,6-dibromophenol dibromophenol

2. What is the IUPAC name of the following compound?

nitrobenzaldehyde a. 3-bromo-4-nitrobenzaldehyde b. 2-bromo-1-nitro-4-benzoic acid benzoic ____

c. 3-bromo-4-nitroacetophenone d. 3-bromo-4-nitrobenzoic acid d. cycloocta-1,3,5,7 1,3,5,7-tetraene

3. Which of the following compounds is aromatic? a. ethane b. cyclobuta-1,3 1,3-diene c. benzene

____

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

a.

c.

b.

d.

____ ____

5. Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3? a. benzene b. nitrobenzene c. bromobenzene d. benzaldehyde 6. Which of the following sets of substituents are all o/p o/p-directing in electrophilic aromatic substitution reactions? a. Cl, CH3, CN b. Br, OH, COCH3 c. Cl, OH, CH3 d. CN, NO2, COCH3

____

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

____

a.

c.

b.

d.

___

9. Which of the following is a correct statement regarding electrophilic aromatic substitution? a. The carbocation intermediate will lose a proton to regain aromaticity, usually from a position other than the site of electrophilic attack. b. Formation of the carbocation intermediate has a high activation barrier due to loss of aromaticity. c. The carbocation intermediate has several resonance structures and is negatively charged. d. Re-formation of the aromatic ring has a low activation barrier and therefore occurs slo formation slowly. e. Many suitable electrophiles are unreactive and can be stored for long periods of time prior to use.

____ 10. Place the following in order of reactivity towards electrophilic aromatic substitution.

a. I > II > III > IV Problem

b. I > II > IV > III

c. II > I > III > IV

d. II > I > IV > III

e. III > IV > II > I

11. Consider the following sequence of reactions:

a)

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

a. b)

b.

c.

d.

If KMnO4 had been replaced by Na2Cr2O7, what would be the final product of the reaction?

Instructions: Consider the reaction below to answer the following question(s).

12. Refer to instructions. The Lewis acid catalyst in the reaction is indicated by letter _____. 13. Circle the aromatic portion of the following molecule:

14. Draw the structure of 3,5-dimethylphenol. dimethylphenol. Instructions: Provide the IUPAC name for each of the following compounds. 15. IUPAC Name:

16. IUPAC Name:

17. IUPAC Name:

18. IUPAC Name:

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

19. What is the role of the AlCl3 in the reaction? Instructions:Starting with benzene or toluene, how would you synthesize these compounds? Assume ortho and para isomers can be separated. 20. Synthesize

Answer Section MULTIPLE CHOICE 1. ANS: B 2. ANS: D 3. ANS: C 4. ANS: C 5. ANS: A 6. ANS: C 7. ANS: A 8. ANS: A 9. ANS: B 10. ANS: B PROBLEM 11. ANS: a) c b) No change, the product would still be the oxidation of the alkyl side chain. PTS: 1 PTS: 1 PTS: 1 PTS: 1 PTS: 1 PTS: 1 PTS: 1 PTS: 1 PTS: 1 PTS: 1

PTS: 1 12. ANS: C PTS: 1 13. ANS:

PTS: 1 14. ANS:

PTS: 1 15. ANS: isopropylbenzene or cumene PTS: 1 16. ANS: cis-1-methyl-3-phenylcyclohexane phenylcyclohexane PTS: 1 17. ANS: 2,4-diaminotoluene PTS: 1 18. ANS: (E)-2,3-diphenyl-2-butene PTS: 1 19. ANS: The AlCl3 is a Lewis acid catalyst that assists in the ionization of the alkyl halide to give the carbocation electrophile. PTS: 1 20. ANS:

PTS: 1