Chapter 22 Exam Questions Benzene Electrophilic Substitution - Chemistry 3 4e | Test Bank Burrows by Andrew Burrows. DOCX document preview.

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Chapter 22 Exam Questions Benzene Electrophilic Substitution

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

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Type: matching question

Title: Chapter 22 Question 01

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

Section reference: 22.1

a. 1 = Aromatic molecule

b. 2 = Conjugated molecule

c. 3 = Alkene

d. 4 = Radical

e. 5 = Anti-aromatic molecule

Type: multiple choice question

Title: Chapter 22 Question 02

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

A chemical structure of cyclopentadienyl anion shows a five membered ring C 5 bonded with an anion having a lone pair of electrons. (A) A chemical structure shows a five membered ring C 5 put inside an energy circle, which gives the bottom three C atoms having a paired electrons, in turn. (B) A chemical structure shows a five membered ring C 5 put inside an energy circle, which gives the bottom C atom having a paired electrons, and the left and right C atoms have an unpaired electron. (C) A chemical structure shows a five membered ring C 5 put inside an energy circle, which gives the two bottom C atoms having a paired electrons, in turn. (D) A chemical structure shows a five membered ring C 5 put inside an energy circle, which gives the two bottom C atoms having a paired electrons, in turn. The left and right C atoms have an unpaired electron, in turn.

a. A

Section reference: 22.1

b. B

Section reference: 22.1

c. C

Section reference: 22.1

d. D

Section reference: 22.1

Type: multiple choice question

Title: Chapter 22 Question 03

3) How many bonding molecular orbitals are present in cyclobutadiene?

a. 0

Section reference: 22.1

b. 1

Section reference: 22.1

c. 2

Section reference: 22.1

d. 3

Section reference: 22.1

e. 4

Section reference: 22.1

Type: multiple response question question

Title: Chapter 22 Question 04

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

a. have (4n + 2) sigma-electrons.

Section reference: 22.1

b. have 6 pi-electrons.

Section reference: 22.1

c. possess uninterrupted (continuous) conjugation.

Section reference: 22.1

d. be cyclic.

Section reference: 22.1

e. be planar.

Section reference: 22.1

f. F: be neutral (no charge)

Section reference: 22.1

Type: multiple response question question

Title: Chapter 22 Question 05

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

a. All aromatic molecules have the same amount of resonance stabilisation.

Section reference: 22.1

b. Aromatic molecules are more stable than conjugated molecules.

Section reference: 22.1

c. Conjugated molecules can be either cyclic or acyclic.

Section reference: 22.1

d. All aromatic molecules have 4n pi-electrons.

Section reference: 22.1

e. Conjugated molecules are less stable than anti-aromatic molecules.

Section reference: 22.1

Type: multiple response question question

Title: Chapter 22 Question 06

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

(A) A chemical structure shows a six membered C 5 C negative ring with a lone pair of electrons. (B) A chemical structure shows a seven membered C 7 ring. (C) A chemical structure shows a six membered C 6 ring double bonded with an O atom, where an O atom is double bonded with the C atom at para position. (D) A chemical structure shows a six membered C 5 C positive ring single bonded with N O 2. (E) A chemical structure shows a five membered C 4 S ring.

a. A

Section reference: 22.1

b. B

Section reference: 22.1

c. C

Section reference: 22.1

d. D

Section reference: 22.1

e. E

Section reference: 22.1

Type: multiple response question question

Title: Chapter 22 Question 07

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

(A) A chemical structure shows a five membered C 4 (B e) ring. (B) A chemical structure shows a five membered C 4 (B H) ring. (C) A chemical structure shows a five membered C 4 (C H 2) ring. (D) A chemical structure shows a five membered C 4 (N H) ring. (E) A chemical structure shows a five membered C 4 O ring.

a. A

Section reference: 22.1

b. B

Section reference: 22.1

c. C

Section reference: 22.1

d. D

Section reference: 22.1

e. E

Section reference: 22.1

Type: multiple response question question

Title: Chapter 22 Question 08

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

(A) A chemical structure shows C H 2 double bond C H single bond C H double bond C H single bond C H double bond C H 2. (B) A chemical structure of a six membered ring C 6 has a lone electron on two opposite sides of the ring. (C) A chemical structure shows a six membered C 4 (B H) (N H) ring. (D) A chemical structure shows two six membered C 6 rings attached with two common C atoms. (E) A chemical structure shows two six membered C 6 rings attached, having two common C atoms.

a. A

Section reference: 22.1

b. B

Section reference: 22.1

c. C

Section reference: 22.1

d. D

Section reference: 22.1

e. E

Section reference: 22.1

Type: multiple choice question

Title: Chapter 22 Question 09

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

(A) A chemical structure shows a six membered C 5 N ring. (B) A chemical structure shows a six membered C 6 ring. (C) A chemical structure shows a five membered C 4 O ring. (D) A chemical structure shows a five membered C 4 (N H) ring. (E) A chemical structure shows a four membered C 4 ring.

a. A

Section reference: 22.1

b. B

Section reference: 22.1

c. C

Section reference: 22.1

d. D

Section reference: 22.1

e. E

Section reference: 22.1

Type: multiple response question question

Title: Chapter 22 Question 10

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

A chemical structure of isopropylbenzene shows a six membered C 6 ring single bonded with C H molecule, where two C H 3 molecules are single bonded with C H molecule. (A) A chemical reaction shows a six membered C 6 ring under a carbon chain of three C atoms, where third C atom is single bonded with a C l atom and under A l C l 3, gives a product. (B) A chemical reaction shows a six membered C 6 ring under C H 3 single bond C H (C l) single bond C H 3 and A l C l 3, gives a product. (C) A chemical reaction shows a six membered C 6 ring under C H 3 single bond C H double bond C H 2 and H 2 S O 4, gives a product. (D) A chemical reaction shows a six membered C 6 ring C H 3 single bond C H (O H) single bond C H 3 and H 2 S O 4, gives a product. (E) A chemical reaction shows a six membered C 6 ring single bonded with S O 3 H, where C H (C H 3) (C H 3) is single bonded with the C atom at an ortho position under dilute H 2 S O 4, gives a product.

a. A

Section reference: 22.2

b. B

Section reference: 22.2

c. C

Section reference: 22.2

d. D

Section reference: 22.2

e. E

Section reference: 22.2

Type: multiple choice question

Title: Chapter 22 Question 11

11) What is the major product of the following reaction?

A chemical reaction shows a six membered C 6 ring single bonded with O M e under a carbon chain of three atoms, where second C atom is single bonded with C H 3 and third C atom is single bonded with C l and under A l C l 3, gives a product. (A) A chemical structure shows a six membered C 6 ring single bonded with O M e, where a carbon chain of three C atoms is single bonded with the same C atom at para position, where second C atom of carbon chain is single bonded with C H 3. (B) A chemical structure shows a six membered C 6 ring single bonded with O M e, where t dash B u is single bonded with the C atom at para position. (C) A chemical structure shows a six membered C 6 ring single bonded with O M e, where t dash B u is single bonded with the same C atom at an ortho position. (D) A chemical structure shows a six membered C 6 ring single bonded with O H, where C l atom is single bonded with the same C atom at para position.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

d. D

Section reference: 22.3

Type: multiple choice question

Title: Chapter 22 Question 12

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

(A) A chemical structure shows a six membered C 6 ring single bonded with O M e. (B) A chemical structure shows a six membered C 6 ring single bonded with another C atom, where C atom is single bonded with C H 3 and double bonded with an O atom. (C) A chemical structure shows a six membered C 6 ring single bonded with M e. (D) A chemical structure shows a C atom double bonded with an O atom and single bonded with C H 3 and H N, where H N is single bonded with a six membered C 6 ring. (E) A chemical structure shows a six membered C 6 ring single bonded with C l.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

d. D

Section reference: 22.3

e. E

Section reference: 22.3

Type: multiple response question question

Title: Chapter 22 Question 13

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 chemical structure shows a six membered C 6 ring single bonded with N O 2. (B)A chemical structure shows a six membered C 6 ring single bonded with positive N M e 3 along with C l negative. (C) A chemical structure shows a six membered C 6 ring single bonded with M e. (D) A chemical structure shows a six membered C 6 ring single bonded with O M e. (E) A chemical structure shows a six membered C 6 ring single bonded with C l.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

d. D

Section reference: 22.3

e. E

Section reference: 22.3

Type: multiple choice question

Title: Chapter 22 Question 14

14) For the following reaction, pick out the major product:

A chemical structure shows a six membered C 6 ring single bonded with N M e 2 under H N O 3 and H 2 S O 4, gives a product. (A) A chemical structure shows a six membered C 6 ring single bonded with N M e 2, where N O 2 is single bonded with the same C atom at meta position. (B) A chemical structure shows a six membered C 6 ring single bonded with N M e 2, where N O 2 is single bonded with the same C atom at para position. (C) A chemical structure shows a six membered C 6 ring single bonded with N M e 2, where S O 3 H is single bonded with the same C atom at meta position. (D) A chemical structure shows a six membered C 6 ring i single bonded with N M e 2, where S O 3 H is single bonded with the same C atom at para position.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

d. D

Section reference: 22.3

Type: matching question

Title: Chapter 22 Question 15

15) Match the following electronic effects to the substituents:

Section reference: 22.3

a. ‑CH3 = +I effect, no M effect

b. ‑Ph = +I effect, +M effect

c. ‑CH=CH-CHO = +I effect, ‑M effect

d. ‑NH2 = ‑I effect, +M effect

e. ‑NO2 = ‑I effect, ‑M effect

Type: multiple choice question

Title: Chapter 22 Question 16

16) For the following reaction, pick out the major product:

A chemical structure shows a six membered C 6 ring single bonded with C l under a C atom is double bonded with an O atom and single bonded with t dash B u and C l and under A l C l 3, gives a product. (A) A chemical structure shows a six membered C 6 ring single bonded with C l, where another C atom is single bonded with the C atom at para position, where C atom is double bonded with an O atom and single bonded with t-B u. (B) A chemical structure shows a six membered C 6 ring single bonded with C l, where another C atom is single bonded with the C atom at meta position, where C atom is single bonded with t dash B u and double bonded with an O atom. (C) A chemical structure shows a six membered C 6 ring single bonded with C l, where t dash B u is single bonded with the C atom at para position. (D) A chemical structure shows a six membered C 6 ring single bonded with C l, where another C atom is single bonded with the C atom at an ortho position, where C atom is double bonded with an O atom and single bonded with t-B u.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

d. D

Section reference: 22.3

Type: multiple choice question

Title: Chapter 22 Question 17

17) From the following reaction, pick out the major product:

A chemical reaction shows a six membered C 6 ring single bond N H single bond C O single bond another six membered C 6 ring under C l 2 and A l C l 3, gives a product. (A) A chemical structure shows a six membered C 6 ring single bond N H single bond C O single bond another six membered C 6 ring, where C l is single bonded with the C atom of the first C 6 ring at meta position. (B) A chemical structure shows a six membered C 6 ring single bond N H single bond C O single bond another six membered C 6 ring, where C l is single bonded with the C atom of the first C 6 ring at para position. (C) A chemical structure shows a six membered C 6 ring single bond N H single bond C O single bond another six membered C 6 ring, where C l is single bonded with the C atom of the second C 6 ring at ortho position. (D) A chemical structure shows a six membered C 6 ring single bond N H single bond C O single bond another six membered C 6 ring, where C l is single bonded with the C atom of the second C 6 ring at meta position.

a. A

Section reference: 22.4

b. B

Section reference: 22.4

c. C

Section reference: 22.4

d. D

Section reference: 22.4

Type: matching question

Title: Chapter 22 Question 18

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

A chemical reaction shows a six membered C 6 ring single bonded with C H 3 under step 1, gives a six membered C 6 ring is single bonded with C H, where C H is single bonded with two B r, under step 2, gives a six membered C 6 ring is single bonded with C H O, under step 3, gives a six membered C 6 ring is single bonded with another c atom, where C atom is single bonded with H O and double bonded with an O atom, under step 4, gives a six membered C 6 ring is single bonded with M e O and double bonded with an O atom.

Section reference: 22.4

a. H2O = Step 2

b. MeOH, HCl = Step 4

c. KMnO4, H2O = Step 3

d. excess Br2, hv = Step 1

Type: matching question

Title: Chapter 22 Question 19

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

A chemical reaction shows a benzene ring under 1. Reagents A and 2. Reagents B gives a six membered ring single bonded with C (C H 3) 3, where C O C H (C H 3) 2 is attached at meta position, under 3. Reagents 3 and 4. Reagents 4 gives a six membered ring single bonded with C (C H 3) 3, where C H 2 C H (C H 3) C H 3 is attached at right ortho position, and C H 3 C H 2 C H 2 is attached with the left ortho position.

Section reference: 22.4

a. EtCOCl, AlCl3 = Reagents 3

b. Zn/Hg, HCl = Reagents 4

c. t-BuCl, AlCl3 = Reagents B

d. i-PrCOCl, AlCl3 = Reagents A

Type: matching question

Title: Chapter 22 Question 20

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

A chemical reaction shows a six membered C 6 ring single bonded with N H 2, where two C l are single bonded with the C atom at two different ortho position and N O 2 is single bonded with the C atom at para position under 1. H O N O and 2. C u C, gives a product A, under 1. S n comma H C l and 2. N a O H comma H 2 O, gives a product B, under 1. H O N O and 2.H 3 P O 2, gives a product C.

Section reference: 22.4

a. A chemical structure shows a six membered C 6 ring single bonded with Cl, where another two C l are single bonded with the C atom at two different ortho position and N H 2 is single bonded with the C atom at para position. = Product B

b. A chemical structure shows a six membered C 6 ring single bonded with Cl, where another two C l are single bonded with the C atom at two different ortho position and N O 2 is single bonded with the C atom at para position. = Product A

c. A chemical structure shows a six membered C 6 ring single bonded with Cl, where another two C l are single bonded with the C atom at ortho and meta position. = Product C

Type: multiple choice question

Title: Chapter 22 Question 21

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

A chemical reaction shows a six membered C 6 ring single bonded with M e under B r 2 and F e B r 3, gives a product. (A) A chemical structure shows a six membered C 6 ring single bonded with C H 2 (B r). (B) A chemical structure shows a six membered C 6 ring single bonded with M e, where F e is single bonded with the C atom at an ortho position. (C) A chemical structure shows a six membered C 6 ring single bonded with M e, where B r is single bonded with the C atom at a meta position. (D) A chemical structure shows a six membered C 6 ring single bonded with M e, where B r is single bonded with the C atom at para position. (E) A chemical structure shows a six membered C 6 ring single bonded with M e, where two B r atoms are single bonded with the C atom at an ortho and para position.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

d. D

Section reference: 22.3

e. E

Section reference: 22.3

Type: multiple choice question

Title: Chapter 22 Question 22

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

A chemical reaction shows a C atom double bonded with an O atom and single bonded with M e and an O atom, where O atom is single bonded with a six membered C 6 ring, under aqueous H N O 3 and H 2 S O 4, gives a question mark. (A) A chemical structure shows a C atom double bonded with an O atom and single bonded with M e and an O atom, where O atom is single bonded with a six membered C 6 ring, where S O 3 is single bonded with the C atom of C 6 ring at meta position. (B) A chemical structure shows a C atom double bonded with an O atom and single bonded with M e and an O atom, where O atom is single bonded with a six membered C 6 ring, where N O 2 is single bonded with the C atom of C 6 ring at meta position. (C) A chemical structure shows a C atom double bonded with an O atom and single bonded with M e and an O atom, where O atom is single bonded with a six membered C 6 ring, where N O 2 is single bonded with the C atom of C 6 ring at para position.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

Type: multiple choice question

Title: Chapter 22 Question 23

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

A chemical reaction shows a C atom double bonded with an O atom and single bonded with M e and a six membered C 6 ring under heat and H 2 S O 4, gives a question mark. (A) A chemical structure shows a C atom double bonded with an O atom and single bonded with M e and a six membered C 6 ring, where S O 3 is single bonded with the C atom of C 6 ring at an ortho position. (B) A chemical structure shows a C atom double bonded with an O atom and single bonded with M e and a six membered C 6 ring, where S O 3 is single bonded with the C atom of C 6 ring at para position. (C) A chemical structure shows a C atom double bonded with an O atom and single bonded with M e and a six membered C 6 ring, where S O 3 is single bonded with the C atom of C 6 ring at meta position. (D) A chemical structure shows a C atom double bonded with an O atom and single bonded with M e and a six membered C 6 ring, where N O 2 is single bonded with the C atom of C 6 ring at meta position.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

d. D

Section reference: 22.3

Type: multiple choice question

Title: Chapter 22 Question 24

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

A chemical reaction shows a six membered C 6 ring under another C atom single bonded with three C H 3 molecules and a C l atom left parenthesis 2 equivalent right parenthesis and A l C l 3, gives question mark. (A) A chemical structure shows a six membered C 6 ring single bonded with another C atom, where C atom is single bonded with three C H 3 molecules. (B) A chemical structure shows a six membered C 6 ring single bonded with another C atom, where C atom is single bonded with three C H 3 molecules. Another C atom is single bonded with the C atom of C 6 ring at para position, where C atom is single bonded with three C H 3 molecules. (C) A chemical structure shows a six membered C 6 ring single bonded with another C atom, where C atom is single bonded with three C H 3 molecules. Another C atom is single bonded with the C atom of C 6 ring at meta position, where C atom is single bonded with three C H 3 molecules.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

Type: multiple choice question

Title: Chapter 22 Question 25

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

A chemical reaction shows a six membered C 6 ring single bonded with N H 2 under C l 2 and F e C l 3, gives question mark. (A) A chemical structure shows a six membered C 6 ring single bonded with N H 2, where C l is single bonded with the C atom at an ortho position. (B) A chemical structure shows a six membered C 6 ring single bonded with N H 2, where C l is single bonded with the C atom at meta position. (C) A chemical structure shows a six membered C 6 ring single bonded with N H 2, where two C l atoms are single bonded with the C atom at ortho and meta position. (D) A chemical structure shows a six membered C 6 ring single bonded with N H 2, where C l is single bonded with the C atom at para position. (E) A chemical structure shows a six membered C 6 ring single bonded with N H 2, where two C l atoms are single bonded with the C atom at ortho and para position.

a. A

Section reference: 22.3

b. B

Section reference: 22.3

c. C

Section reference: 22.3

d. D

Section reference: 22.3

e. E

Section reference: 22.3

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Document Type:
DOCX
Chapter Number:
22
Created Date:
Aug 21, 2025
Chapter Name:
Chapter 22 Benzene – Electrophilic Substitution
Author:
Andrew Burrows

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