Deck 5: Aromatic Compounds

Question 1

Circle the compound(s) in the following set that will undergo both substitution and addition when treated with Br₂.

Answer 1

Question 2

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 slowly.
E) Many suitable electrophiles are unreactive and can be stored for long periods of time prior to use.

Answer 2

Formation of the carbocation intermediate has a high activation barrier due to loss of aromaticity.

Question 3

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

A) benzene
B) nitrobenzene
C) bromobenzene
D) benzaldehyde

Answer 3

benzene

Question 4

Which of the following compounds is aromatic?

A) ethane
B) cyclobuta-1,3-diene
C) benzene
D) cycloocta-1,3,5,7-tetraene

Question 5

Consider the following sequence of reactions:
1)What is the major organic product obtained from the sequence of reactions?

A)
B)
C)
D)
2)If KMnO₄ had been replaced by Na₂Cr₂O₇, what would be the final product of the reaction?

Question 6

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

Question 7

Consider the following compound: a)Provide the correct IUPAC name for the compound.
b)Draw and name the other isomeric nitrotoluenes.

Question 8

Draw the resonance structures for acenaphthene.

Question 9

What is the correct assignment of the names of the following aromatic compounds?

A) 1 = anisole; 2 = furan; 3 = pyrimidine
B) 1 = aniline; 2 = pyrrole; 3 = pyridine
C) 1 = anisole; 2 = pyridine; 3 = pyrrole
D) 1 = aniline; 2 = imidazole; 3 = pyridine

Question 10

Draw the structure of 4-bromo-2-fluorotoluene.

Question 11

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

A) I > II > III > IV
B) I > II > IV > III
C) II > I > III > IV
D) II > I > IV > III
E) III > IV > II > I

Question 12

An accurate description of the structure of benzene is:

A) The $\pi$ bonds are quickly moving around the ring.
B) There are two distinct structures that are in equilibrium.
C) All the carbon-carbon bonds are equal in length.
D) There are distinct single and double bonds.
E) Some bonds are longer than others.

Question 13

Which of the following undergoes the most rapid acylation upon treatment with acetyl chloride and AlCl₃?

A) benzene
B) toluene
C) chlorobenzene
D) 1,4-dichlorobenzene

Question 14

Which of the following sets of substituents are all o/p-directing in electrophilic aromatic substitution reactions?

A) Cl, CH₃, CN
B) Br, OH, COCH₃
C) Cl, OH, CH₃
D) CN, NO₂, COCH₃

Question 15

What is the IUPAC name of the following compound?

A) 3-bromo-4-nitrobenzaldehyde
B) 2-bromo-1-nitro-4-benzoic acid
C) 3-bromo-4-nitroacetophenone
D) 3-bromo-4-nitrobenzoic acid

Question 16

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

A)
B)
C)
D)

Question 17

Draw the major product of the following reaction:

Question 18

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.

Question 19

What is the IUPAC name of the following compound?

A) 2,4-dibromotoluene
B) 2,4-dibromophenol
C) 2,4-dibromoaniline
D) 4,6-dibromophenol

Question 20

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

A)
B)
C)
D)

Question 21

Instructions: Provide the IUPAC name for each of the following compounds.
IUPAC Name:

Question 22

Instructions: Provide the IUPAC name for each of the following compounds.
IUPAC Name:

Question 23

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

Refer to instructions. This reaction proceeds _____________ (faster or slower) than benzene.

Question 24

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

Question 25

Draw the structure of p-chlorobenzaldehyde.

Question 26

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

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

Question 27

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

Refer to instructions. Draw the structure of product D.

Question 28

Instructions:
Consider the Friedel-Crafts alkylation reaction below to answer the following questions:
What is the role of the AlCl₃ in the reaction?

Question 29

Draw the structure of p-bromoaniline.

Question 30

Circle the aromatic portion of the following molecule:

Question 31

Draw the structure of m-fluoronitrobenzene.

Question 32

Which of the following heterocycles is aromatic?

A)
B)
C)
D)

Question 33

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

Refer to instructions. The nucleophile in the reaction is indicated by letter _____.

Question 34

Draw the structure of 3,5-dimethylphenol.

Question 35

Instructions:
Consider the Friedel-Crafts alkylation reaction below to answer the following questions:
Draw the structure of the electrophile in this reaction.

Question 36

Draw the structure of o-hydroxybenzoic acid.

Question 37

Circle the aromatic portion of the following molecule:

Question 38

Instructions: Provide the IUPAC name for each of the following compounds.
IUPAC Name:

Question 39

Instructions: Provide the IUPAC name for each of the following compounds.
IUPAC Name:

Question 40

Instructions: Provide the IUPAC name for each of the following compounds.
IUPAC Name:

Question 41

Instructions:
Choose the best reagent(s) from the list provided below for carrying out the following conversions. Place the letter of the reagent in the box beside the reaction number over the arrow. There is only one answer for each reaction.
a. KMnO₄, H₃O⁺
b. Br₂, FeBr₃
c. Cl₂, FeCl₃
d. CH₃Cl, AlCl₃
e. HNO₃, H₂SO₄
Choose the best reagents:

Question 42

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R."
Write the product:

Question 43

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R."
Write the product:

Question 44

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R."
Write the product:

Question 45

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

Question 46

Instructions:
Choose the best reagent(s) from the list provided below for carrying out the following conversions. Place the letter of the reagent in the box beside the reaction number over the arrow. There is only one answer for each reaction.
a. KMnO₄, H₃O⁺
b. Br₂, FeBr₃
c. Cl₂, FeCl₃
d. CH₃Cl, AlCl₃
e. HNO₃, H₂SO₄
Choose the best reagents:

Question 47

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

Question 48

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R."
Write the product:

Question 49

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R."
Write the product:

Question 50

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R."
Write the product:

Question 51

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R."
Write the product:

Question 52

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R."
Write the product: