Name______________________________________________________________

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

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

a. 3-bromo-4-nitrobenzaldehydeb. 2-bromo-1-nitro-4-benzoic acid

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

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

a.

b.

____ 5. Which of the following undergoes the most rapid bromination upon treatment with Bra. benzene b. nitrobenzene

____ 6. Which of the following sets of substituents are all o/pa. Cl, CH3, CN b. Br, OH, COCH

Name______________________________________________________________ SN______

Identify the choice that best completes the statement or answers the question.

What is the IUPAC name of the following compound?

dibromophenol c. 2,4-dibromoaniline d. 4,6-dibromophenol

What is the IUPAC name of the following compound?

nitrobenzaldehyde c. 3-bromo-4-nitroacetophenone benzoic acid d. 3-bromo-4-nitrobenzoic acid

Which of the following compounds is aromatic? 1,3-diene c. benzene d. cycloocta-1,3,5,7

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

c.

d.

Which of the following undergoes the most rapid bromination upon treatment with Brnitrobenzene c. bromobenzene d. benzaldehyde

Which of the following sets of substituents are all o/p-directing in electrophilic aromatic substitution reactions?Br, OH, COCH3 c. Cl, OH, CH3 d. CN, NO

SN______

Identify the choice that best completes the statement or answers the question.

dibromophenol

1,3,5,7-tetraene

Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?

electrophilic aromatic substitution reactions? CN, NO2, COCH3

____ 7. Which of the following sets of substituents are all reactions? a. Cl, CN, NO2 b. Cl, NH

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

a.

b.

___ 9. Which of the following is a correct statement regarding electrophilica. 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

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 sloe. 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 b. I > II > IV

Problem

11. Consider the following sequence of reactions:

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

Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution

Cl, NH2, CH3 c. CH3, OCH3, COCH3 d.

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

c.

d.

Which of the following is a correct statement regarding electrophilic aromatic substitution?The carbocation intermediate will lose a proton to regain aromaticity, usually from a position other than the site of electrophilic attack. Formation of the carbocation intermediate has a high activation barrier due to loss of

The carbocation intermediate has several resonance structures and is negatively charged.formation of the aromatic ring has a low activation barrier and therefore occurs slo

Many suitable electrophiles are unreactive and can be stored for long periods of time prior

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

I > II > IV > III c. II > I > III > IV d. II > I > IV > III e.

Consider the following sequence of reactions:

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

in electrophilic aromatic substitution

d. CH3, NH2, OCH3

aromatic substitution? The carbocation intermediate will lose a proton to regain aromaticity, usually from a

intermediate has a high activation barrier due to loss of

The carbocation intermediate has several resonance structures and is negatively charged. formation of the aromatic ring has a low activation barrier and therefore occurs slowly.

Many suitable electrophiles are unreactive and can be stored for long periods of time prior

e. III > IV > II > I

a. b. b) If KMnO4 had been replaced by Na 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. Instructions: Provide the IUPAC name for each of the following compounds.

15. IUPAC Name:

16. IUPAC Name:

17. IUPAC Name:

18. IUPAC Name:

c. d.

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

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

Refer to instructions. The Lewis acid catalyst in the reaction is indicated by letter _____.

Circle the aromatic portion of the following molecule:

dimethylphenol.

Provide the IUPAC name for each of the following compounds.

, what would be the final product of the reaction?

_____.

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

19. What is the role of the AlCl3 in the reaction?

Instructions:Starting with benzene or toluene, how would you synthesize these compounds? Assume and para isomers can be separated.

20. Synthesize

Crafts alkylation reaction below to answer the following questions:

in the reaction?

with benzene or toluene, how would you synthesize these compounds? Assume isomers can be separated.

Crafts alkylation reaction below to answer the following questions:

with benzene or toluene, how would you synthesize these compounds? Assume ortho

Answer Section

MULTIPLE CHOICE

1. ANS: B PTS: 1

2. ANS: D PTS: 1

3. ANS: C PTS: 1

4. ANS: C PTS: 1

5. ANS: A PTS: 1

6. ANS: C PTS: 1

7. ANS: A PTS: 1

8. ANS: A PTS: 1

9. ANS: B PTS: 1

10. ANS: B PTS: 1

PROBLEM

11. ANS: a) c b) No change, the product would still be the oxidation of the alkyl side chain. PTS: 1

12. ANS: C PTS: 1

13. ANS:

PTS: 1

14. ANS:

No change, the product would still be the oxidation of the alkyl side chain.

PTS: 1

15. ANS: isopropylbenzene or cumene PTS: 1

16. ANS: cis-1-methyl-3-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

phenylcyclohexane

is a Lewis acid catalyst that assists in the ionization of the alkyl halide to give the carbocation

is a Lewis acid catalyst that assists in the ionization of the alkyl halide to give the carbocation