Deck 22: Benzene and Other Aromatic Compounds: Electrophilic Substitution Reactions

Question 1

Place the following types of species in order of (electronic) stability, with 1 being the most stable and 5 the least stable:

A) Aromatic molecule
B) Radical
C) Anti-aromatic molecule
D) Alkene
E) Conjugated molecule

Answer 1

A, E, D, B, C

Question 2

From the following Frost diagrams, A-D, pick out the correct one for a cyclopentadienyl anion:

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

Answer 2

A

Question 3

How many bonding molecular orbitals are present in cyclobutadiene?

A) 0
B) 1
C) 2
D) 3
E) 4

Answer 3

B

Question 4

Complete the following statement: 'For a molecule to be aromatic it must ….' Please select all that apply.

A) have (4n + 2) sigma-electrons.
B) have 6 pi-electrons.
C) possess uninterrupted (continuous) conjugation.
D) be cyclic.
E) be planar.

Question 5

Which of the following statements are true? Please select all that apply.

A) All aromatic molecules have the same amount of resonance stabilisation.
B) Aromatic molecules are more stable than conjugated molecules.
C) Conjugated molecules can be either cyclic or acyclic.
D) All aromatic molecules have 4n pi-electrons.
E) Conjugated molecules are less stable than anti-aromatic molecules.

Question 6

From the following species, A-E, pick out those which have uninterrupted (continuous) conjugation. Please select all that apply.

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

Question 7

From the following molecules, A-E, pick out those which are aromatic. Please select all that apply.

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

Question 8

For the following species, A-E, pick out those which are aromatic. Please select all that apply.

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

Question 9

Which of the following compounds, A-E, exhibits the greatest resonance stabilisation?

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

Question 10

From the following reactions, A-E, pick out those which give isopropylbenzene as the major product. Please select all that apply.

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

Question 11

What is the major product of the following reaction?

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

Question 12

From the following molecules, A-E, pick out the one which is most reactive towards aromatic bromination:

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

Question 13

From the following molecules, A-E, pick out the molecules which react to give predominantly meta-nitration products. Please select all that apply.

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

Question 14

For the following reaction, pick out the major product:

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

Question 15

Match the following electronic effects to the substituents:

--CH₃

A) +I effect, no M effect
B) +I effect, +M effect
C) +I effect, -M effect
D) -I effect, +M effect
E) -I effect, -M effect

Question 16

Match the following electronic effects to the substituents:

--Ph

A) +I effect, no M effect
B) +I effect, +M effect
C) +I effect, -M effect
D) -I effect, +M effect
E) -I effect, -M effect

Question 17

Match the following electronic effects to the substituents:
--CH=CH-CHO

A) +I effect, no M effect
B) +I effect, +M effect
C) +I effect, -M effect
D) -I effect, +M effect
E) -I effect, -M effect

Question 18

Match the following electronic effects to the substituents:
--NH₂

A) +I effect, no M effect
B) +I effect, +M effect
C) +I effect, -M effect
D) -I effect, +M effect
E) -I effect, -M effect

Question 19

Match the following electronic effects to the substituents:
--NO₂

A) +I effect, no M effect
B) +I effect, +M effect
C) +I effect, -M effect
D) -I effect, +M effect
E) -I effect, -M effect

Question 20

For the following reaction, pick out the major product:

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

Question 21

From the following reaction, pick out the major product:

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

Question 22

From the following sequence of reactions, match the reagents to steps 1-4:

-H₂O

A) Step 2
B) Step 4
C) Step 3
D) Step 1

Question 23

From the following sequence of reactions, match the reagents to steps 1-4:

-MeOH, HCl

A) Step 2
B) Step 4
C) Step 3
D) Step 1

Question 24

From the following sequence of reactions, match the reagents to steps 1-4:

-KMnO₄, H₂O

A) Step 2
B) Step 4
C) Step 3
D) Step 1

Question 25

From the following sequence of reactions, match the reagents to steps 1-4:

-excess Br₂, hv

A) Step 2
B) Step 4
C) Step 3
D) Step 1

Question 26

From the following sequence of reactions, match the reagents to steps 1-4:

-EtCOCl, AlCl₃

A) Reagents 3
B) Reagents 4
C) Reagents B
D) Reagents A

Question 27

From the following sequence of reactions, match the reagents to steps 1-4:

-Zn/Hg, HCl

A) Reagents 3
B) Reagents 4
C) Reagents B
D) Reagents A

Question 28

From the following sequence of reactions, match the reagents to steps 1-4:

-t-BuCl, AlCl₃

A) Reagents 3
B) Reagents 4
C) Reagents B
D) Reagents A

Question 29

From the following sequence of reactions, match the reagents to steps 1-4:

-i-PrCOCl, AlCl₃

A) Reagents 3
B) Reagents 4
C) Reagents B
D) Reagents A

Question 30

For the following reaction sequence, match the products, A-C, to the given structures.

-

A) Product B
B) Product A
C) Product C

Question 31

For the following reaction sequence, match the products, A-C, to the given structures.

-

A) Product B
B) Product A
C) Product C

Question 32

For the following reaction sequence, match the products, A-C, to the given structures.

-

A) Product B
B) Product A
C) Product C

Question 33

Which of the following will be the dominant product of this reaction?

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

Question 34

Which of the following will be the dominant product of this reaction?

A) A
B) B
C) C

Question 35

Which of the following will be the dominant product of this reaction?

Redraw instructions from author: Product structures x4, should be SO3H (subscript 3), not SO3 (subscript 3) i.e. add an H to each of the four groups in A-D

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

Question 36

Which of the following will be the dominant product of this reaction?

A) A
B) B
C) C

Question 37

Which of the following will be the dominant product of this reaction?

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