Deck 9: Aromatic Compounds

Question 1

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 1

Cl, CN, NO₂

Question 2

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

Answer 2

Question 3

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

A)

​
B)

​
C)

​
D)

​

Answer 3

​

Question 4

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

Question 5

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 6

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 7

Which of the following would be an o/p-director in a nucleophilic aromatic substitution reaction?

A) −CH₃
B) −OH
C) −F
D) −CN
E) all of these

Question 8

Predict the major product of each of the following reactions.

Question 9

How many π electrons are present in the following heterocycle?

A) 2
B) 4
C) 6
D) 8
E) 10

Question 10

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

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

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

Which of the following does not correctly characterize a nucleophilic aromatic substitution reaction?

A) favored by electron-withdrawing groups
B) carbanion intermediates
C) −NO₂ and −CHO activate the ring
D) −NO₂ and −CHO are o/p-directors
E) an H atom is replaced on the ring

Question 13

Which of the following statements is true about the structure of benzene?

A) six atomic 2p orbitals interact to form six π molecular orbitals
B) there are three bonding π molecular orbitals and three π antibonding molecular orbitals
C) the ground state electronic configuration of benzene has six electrons in three π bonding molecular orbitals
D) the carbon−carbon bonds are all the same length
E) All of these

Question 14

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 15

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 16

Draw the resonance structures for acenaphthene.

Question 17

Which of the following represents the energy levels of the molecular orbitals of benzene?

A)

B)

C)

D)

Question 18

Which of the following statements correctly characterizes the following compound?

A) contains 6 π electrons and is aromatic
B) contains 6 π electrons and is nonaromatic
C) contains 8 π electrons and is antiaromatic
D) contains 8 π electrons and is aromatic
E) contains 8 π electrons and is nonaromatic

Question 19

Which of the following heterocycles is aromatic?

A)

B)

C)

D)

Question 20

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 21

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 22

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

A)

B)

C)

D)

Question 23

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

A)

B)

C)

D)

Question 24

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

A)

B)

C)

D)

Question 25

An accurate description of the structure of benzene is:

A) The π 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 26

Predict the major product of the following reaction:

Question 27

What is the electrophile in the reaction of benzene with acetyl chloride, CH₃COCl, and AlCl₃?

A) CH₃C
O⁺
B) CH₃⁺
C) CH₃CO₂−
D) benzene

Question 28

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

Question 29

Draw the major product of the following reaction:

Question 30

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

A)A
B)B
C)C
D)D

Question 31

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

A)

B)

C)

D)

Question 32

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

Question 33

Consider the following reaction: a)Predict the major product of the reaction.
b)If steps 2 and 3 were reversed, what effect would this have on the major product?

Question 34

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 35

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?

Question 36

Consider the reaction below to answer the following question(s).
Refer to instructions. The Lewis acid catalyst in the reaction is indicated by letter _____.

A)A
B)B
C)C
D)D

Question 37

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