Deck 5: Aromatic Compounds

Question 1

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

A)
B)
C)
D)

Answer 1

C

Question 2

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

Answer 2

A

Question 3

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

Answer 3

B

Question 4

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.

Question 5

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 6

An accurate description of the structure of benzene is:

A) The p 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 7

Consider the following sequence of reactions:

Question 8

Draw the major product of the following reaction:

Question 9

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 10

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 11

Which of the following compounds is aromatic?

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

Question 12

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 13

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

Question 14

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

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

Question 15

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 16

Consider the following compound:

Question 17

Draw the resonance structures for acenaphthene.

Question 18

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

Question 19

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

Question 20

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

A)
B)
C)
D)

Question 21

Circle the aromatic portion of the following molecule:

Question 22

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

Question 23

Instructions:
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.

Question 24

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

Question 25

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 26

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

Question 27

Draw the structure of p-bromoaniline.

Question 28

Circle the aromatic portion of the following molecule:

Question 29

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

Question 30

Draw the structure of o-hydroxybenzoic acid.

Question 31

Instructions: Consider the reaction below to answer the following question(s). Refer to instructions. Draw the structure of product
D.

Question 32

Draw the structure of p-chlorobenzaldehyde.

Question 33

Draw the structure of m-fluoronitrobenzene.

Question 34

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

Question 35

Instructions: Consider the reaction below to answer the following question(s). Refer to instructions. The nucleophile in the reaction is indicated by letter _____.

Question 36

Instructions: Consider the reaction below to answer the following question(s). Refer to instructions. This reaction proceeds _____________ (faster or slower) than benzene.

Question 37

Draw the structure of 3,5-dimethylphenol.

Question 38

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

Question 39

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

Question 40

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 41

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

Question 44

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 45

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 46

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

Question 47

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 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: