Ch20 Halogenoalkanes Substitution And Verified Test Bank - Chemistry 3 4e | Test Bank Burrows by Andrew Burrows. DOCX document preview.

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Ch20 Halogenoalkanes Substitution And Verified Test Bank

Chapter 20: Halogenoalkanes: Substitution and Elimination Reactions

Test Bank

Type: matching question

Title: Chapter 20 Question 01

1) Match the chemical descriptors to the following molecules:

(A) A chemical structure shows a B atom single bonded with three C H 3 molecules. (B) A chemical structure shows a N atom single bonded with three C H 3 molecules. (C) A chemical structure shows a C atom single bonded with two C H 3 molecules and B r atom. (D) A chemical structure shows a C atom single bonded with two C H 3 molecules and double bonded with a N H molecule.

Section reference: 20.1 and 19.1

a. Weak electrophile = C

b. Strong electrophile = A

c. Weak nucleophile = D

d. Strong nucleophile = B

Type: multiple choice question

Title: Chapter 20 Question 02

2) From the following anions, pick out the one which is the most stable leaving group.

a. A

Section reference: 20.2

b. B

Section reference: 20.2

c. C

Section reference: 20.2

d. D

Section reference: 20.2

e. E

Section reference: 20.2

Type: multiple choice question

Title: Chapter 20 Question 03

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

A chemical reaction shows a six membered C 6 ring single bonded with a C H 3 molecule under B r 2 and h v, 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 a C H 3 molecule, where a B r atom is single bonded with the same C atom at an ortho position. (C) A chemical structure shows a six membered C 6 ring single bonded with a C H 3 molecule, where a B r atom is single bonded with the same C atom at meta position. (D) A chemical structure shows a six membered C 6 ring single bonded with a C H 3 molecule, where a B r atom is single bonded with the same C atom at para position.

a. A

Section reference: 20.2

b. B

Section reference: 20.2

c. C

Section reference: 20.2

d. D

Section reference: 20.2

Type: matching question

Title: Chapter 20 Question 04

4) Match the chemical descriptors to the species in the following reaction:

Section reference: 20.2

a. ‑SAc = Nucleophile

b. ‑OTs = Leaving group

c. CH3OTs = Electrophile

d. K+ = Counter ion

Type: multiple choice question

Title: Chapter 20 Question 05

5) For a SN2 reaction, pick out the strongest nucleophile from the following species:

a. A

Section reference: 20.3

b. B

Section reference: 20.3

c. C

Section reference: 20.3

d. D

Section reference: 20.3

e. E

Section reference: 20.3

Type: multiple choice question

Title: Chapter 20 Question 06

6) For the following SN2 reaction, what would be the relative rate of reaction if the concentrations of the alkyl bromide and potassium acetate (CH3CO2K) were tripled?

A chemical reaction shows a C atom single bonded with H, B r, C H 3 and P h under C H 3 C O 2 K and C H 2 C l 2, gives a C atom single bonded with C H 3 C O 2, H, C H 3 and P h.

a. No change in the relative rate

Section reference: 20.3

b. The relative rate will increase by three times

Section reference: 20.3

c. The relative rate will increase by six times

Section reference: 20.3

d. The relative rate will increase by nine times

Section reference: 20.3

Type: multiple response question

Title: Chapter 20 Question 07

7) Which of the following factors increase the rate of an SN1 reaction? Please select all that apply.

a. Concentration of the aliphatic halide

Section reference: 20.3

b. Concentration of the nucleophile

Section reference: 20.3

c. Temperature

Section reference: 20.3

d. Non-polar aprotic solvent

Section reference: 20.3

e. Protic solvent

Section reference: 20.3

f. Polar aprotic solvent

Section reference: 20.3

Type: multiple choice question

Title: Chapter 20 Question 08

8) What product(s) would you expect from the following SN2 reaction?

A chemical reaction shows a six membered C 6 ring single bonded with C (C H 3) (C H 3) (C H 3), where a B r atom is single bonded with the C atom at para position under N a O E t and E t O H, gives a product. (A) A chemical structure shows a six membered C 6 ring single bonded with C (C H 3) (C H 3) (C H 3), where O E t is single bonded with the C atom at para position. (B) A chemical structure shows a six membered C 6 ring single bonded with C (C H 3) (C H 3) (C H 3), where O E t is single bonded with the C atom at para position. (C) A chemical structure shows a six membered C 6 ring single bonded with a C atom, where C atom is single bonded with three C H 3 molecules.

a. A

Section reference: 20.3

b. B

Section reference: 20.3

c. C

Section reference: 20.3

d. Equimolar mixture of A and B

Section reference: 20.3

e. Non-equimolar mixture of A and B

Section reference: 20.3

Type: multiple response question

Title: Chapter 20 Question 09

9) From the following bromides, pick out those which can react by a SN2 mechanism. Please select all that apply.

(A) A chemical structure shows C H 3 single bond C H 2 single bond C O single bond B r. (B) A chemical structure shows B r single bond C H 2 single bond C O single bond C H 3. (C) A chemical structure shows a C atom single bonded with three C H 3 molecules and a B r atom. (D)A chemical structure shows a six membered C 6 ring single bonded with a B r atom. (E) A chemical structure shows a six membered C 6 ring single bonded with a B r atom.

a. A

Section reference: 20.3

b. B

Section reference: 20.3

c. C

Section reference: 20.3

d. D

Section reference: 20.3

e. E

Section reference: 20.3

Type: multiple choice question

Title: Chapter 20 Question 10

10) Which of the following alkyl halides has the fastest rate for a SN1 reaction?

(A) A chemical structure shows a C atom single bonded with three C H 3 molecules and a F atom. (B) A chemical structure shows a C atom single bonded with three C H 3 molecules and a C l atom. (C) A chemical structure shows a C atom single bonded with three C H 3 molecules and a B r atom. (D) A chemical structure shows a C atom single bonded with three C H 3 molecules and a I atom.

a. A

Section reference: 20.3

b. B

Section reference: 20.3

c. C

Section reference: 20.3

d. D

Section reference: 20.3

e. All of the above have the same rate of reaction

Section reference: 20.3

Type: multiple choice question

Title: Chapter 20 Question 11

11) From the following benzylic chlorides, pick out the one which is the poorest electrophile for a SN1 reaction:

(A) A chemical structure shows a six membered C 6 ring single bonded with C H 2 (C l), where another C l is single bonded with the C atom at para position. (B) A chemical structure shows a six membered C 6 ring single bonded with C H 2 (C l), where M e is single bonded with the C atom at para position. (C) A chemical structure shows a six membered C 6 ring single bonded with C H 2 (C l), where M e O is single bonded with the C atom at para position.

a. A

Section reference: 20.3

b. B

Section reference: 20.3

c. C

Section reference: 20.3

Type: multiple choice question

Title: Chapter 20 Question 12

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

A chemical reaction shows a C atom single bonded with another C atom, where first C atom is double bonded with an O atom and single bonded with C H 3 molecule and second C atom is single bonded with a B r atom and C H 3 molecule under t dash B u O K, gives a product. (A) A chemical structure shows a C atom single bonded with another C atom, where first C atom is double bonded with an O atom and single bonded with C H 3 molecule and the second C atom is single bonded with O dash t dash B u and C H 3 molecule. (B) A chemical structure shows a C atom double bonded with another C atom, where first C atom is single bonded with O H and single bonded with C H 3 molecule and the second C atom is single bonded with a B r atom and C H 3 molecule. (C) A chemical structure shows a C atom double bonded with an O atom and single bonded with C H (C H 2) and C H 3 molecule. (D) A chemical structure shows a C atom single bonded with O dash t dash B u and C H 3 and double bonded with C H (C H 3).

a. A

Section reference: 20.5

b. B

Section reference: 20.5

c. C

Section reference: 20.5

d. D

Section reference: 20.5

Type: multiple choice question

Title: Chapter 20 Question 13

13) Which of the following alkyl bromides can react with a base in an E2 elimination?

(A) A chemical structure shows a C atom single bonded with P h and B r. (B) A chemical structure shows C H 3 single bonded with a B r atom. (C) A chemical structure shows a C atom single bonded with t dash B u and B r. (D) A chemical structure shows C H 3 O single bond C O single bond C H 2 single bond B r.

a. A

Section reference: 20.4

b. B

Section reference: 20.4

c. C

Section reference: 20.4

d. D

Section reference: 20.4

e. None of these substrates are capable of E2 elimination

Section reference: 20.4

Type: multiple choice question

Title: Chapter 20 Question 14

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

A chemical reaction shows I negative M e 3 N positive single bond C H (C H 3) single bond C H 2 single bond C H 3 under N a O H and H 2 O, gives a product. (A) A chemical structure shows C H 2 double bond C H single bond C H 2 single bond C H 3. (B) A chemical structure shows C H 3 single bond C H double bond C H single bond C H 3. (C) A chemical structure shows C H 3 single bond C H double bond C H single bond C H 3. (D) A chemical structure shows H O single bond C H (C H 3) single bond C H 2 single bond C H 3.

a. A

Section reference: 20.4

b. B

Section reference: 20.4

c. C

Section reference: 20.4

d. D

Section reference: 20.4

Type: multiple choice question

Title: Chapter 20 Question 15

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

A chemical reaction shows C H 3 single bond C H 2 single bond C H 2 single bond C (C H 3) (C H 3) single bond B r plus K O E t under E t O H and reflux, gives a product. (A) A chemical structure shows C H 3 single bond C H 2 single bond C H 2 single bond C (C H 3) (C H 3) single bond O E t. (B) A chemical structure shows C H 3 single bond C H 2 single bond C H 2 single bond C (C H 3) double bond C H 2. (C) A chemical structure shows C H 3 single bond C H 2 single bond C H double bond C (C H 3) (C H 3). (D) A chemical structure shows C H 3 single bond C H double bond C H single bond C H (C H 3) (C H 3).

a. A

Section reference: 20.4

b. B

Section reference: 20.4

c. C

Section reference: 20.4

d. D

Section reference: 20.4

Type: multiple choice question

Title: Chapter 20 Question 16

16) For E2 elimination, pick out the descriptor which describes the stereochemical outcome of this elimination step.

a. A

Section reference: 20.4

b. B

Section reference: 20.4

c. C

Section reference: 20.4

d. D

Section reference: 20.4

e. E

Section reference: 20.4

Type: multiple choice question

Title: Chapter 20 Question 17

17) What is the major product of the following E2 elimination?

A chemical reaction shows a C atom single bonded with another C atom, where first C atom is single bonded with H, C H 3 and P h and second C atom is single bonded with C l, C H 3 and H under N a O E t and E t O H, gives a product. (A) A chemical structure shows a C atom double bonded with another C atom, where first C atom is single bonded with C H 3 molecule and a P h atom. The second C atom is single bonded with C H 3 molecule and a H atom. (B) A chemical structure shows a C atom single bonded with another C atom, first C atom is single bonded with H, C H 3 and P h. The second C atom is double bonded with C H 2 and single bonded with a H atom. (C) A chemical structure shows a C atom single bonded with another C atom, where first C atom is double bonded with H 2 C and single bonded with P h. The second C atom is single bonded with two H atom and C H 3 molecule. (D) A chemical structure shows a C atom double bonded with another C atom, where first C atom is single bonded with C H 3 and P h. The second C atom is single bonded with H and C H 3.

a. A

Section reference: 20.4

b. B

Section reference: 20.4

c. C

Section reference: 20.4

d. D

Section reference: 20.4

Type: multiple response question

Title: Chapter 20 Question 18

18) From the following reactions, pick out those which do NOT involve carbocation formation. Please select all that apply.

(A) A chemical reaction shows C H single bonded with two C H 3 molecules and a C l atom under N a O E t and E t O H, gives C H is single bonded with C H 3 molecule and double bonded with C H 2 molecule. (B) A chemical reaction shows C H single bonded with C H 3 molecule and double bonded with C H 2 molecule under B r 2 and h n, gives B r single bond C H 2 single bond C H double bond C H 2. (C) A chemical reaction shows a C atom single bonded with three C H 3 molecules and O H molecule under c. H 2 S O 4, gives a C atom is single bonded with two C H 3 molecules and double bonded with C H 2 molecule. (D) A chemical reaction shows C H 3 single bond C H (B r) single bond C H 2 single bond C H 3 under N a O A c and E t O H, gives C H 3 single bond C H (O A c) single bond C H 2 single bond C H 3.

a. A

Section reference: 20.5

b. B

Section reference: 20.5

c. C

Section reference: 20.5

d. D

Section reference: 20.5

Type: multiple response question

Title: Chapter 20 Question 19

19) From the following chlorides, pick out those which are capable of undergoing SN1 or SN2 reactions. Please select all that apply.

(A) A chemical structure shows C H 3 single bond C H double bond C H single bond C H (C H 3) single bond C H 2 single bond C l. (B) A chemical structure shows C H 3 single bond C H double bond C H single bond C (C H 3) (C l) single bond C H 3. (C) A chemical structure shows C H 3 single bond C H double bond C (C l) single bond C H (C H 3) single bond C H 3. (D) A chemical structure shows C H 3 single bond C (C l) double bond C H single bond C H (C H 3) single bond C H 3. (E) A chemical structure shows C l single bond C H 2 single bond C H double bond C H single bond C H (C H 3) single bond C H 3.

a. A

Section reference: 20.5

b. B

Section reference: 20.5

c. C

Section reference: 20.5

d. D

Section reference: 20.5

e. E

Section reference: Section 20.5

Type: multiple choice question

Title: Chapter 20 Question 20

20) Which is the major product of the following reaction?

A chemical reaction shows a six membered C 6 ring single bonded with O A c, where t dash B u is single bonded with the same C atom at para position under N a O E t and E t O H, gives a product. (A) A chemical structure shows a six membered C 6 ring single bonded with O E t, where t dash B u is single bonded with the C atom at para position. (B) A chemical structure shows a six membered C 6 ring single bonded with O E t, 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 H, 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 double bonded with an O atom, where t dash B u is single bonded with the C atom at para position. (E) A chemical structure shows a six membered C 6 ring single bonded with t dash B u. A double bond between C atoms is in top right position of ring.

a. A

Section reference: 20.5

b. B

Section reference: 20.5

c. C

Section reference: 20.5

d. D

Section reference: 20.5

e. E

Section reference: 20.5

Type: multiple response question

Title: Chapter 20 Question 21

21) Identify the final products and by-products of the following activation reaction. Please select all that apply.

A chemical reaction shows H 3 C single bonded with O H plus a S atom is single bonded with two C l atom and double bonded with an O atom under pyridine, gives a product.

Section reference: 20.2

a. H3C–Cl

b. H3C–SO2Cl

c. Cl–

d. SO2

Type: multiple choice question

Title: Chapter 20 Question 22

22) Which of the following Newman projections depicts the most reactive conformation of ((2S,3R)-3-bromobutan-2-yl)benzene for undergoing E2 elimination?

(A) A Newman projection view of a chemical structure shows two C atoms are single bonded, where the back C atom is single bonded with B r, M e, and H. The front C atom is single bonded with Ph M e, M e, and H atom. (B) A Newman projection view of a chemical structure shows two C atoms are single bonded, where the back C atom is single bonded with B r, M e, and H. The front C atom is single bonded with Ph M e, M e, and H atom. (C) Newman projection view of a chemical structure shows two C atoms are single bonded, where the back C atom is single bonded with B r, M e, and H. The front C atom is single bonded with Ph M e, M e, and H atom. (D) A Newman projection view of a chemical structure shows two C atoms are single bonded, where the back C atom is single bonded with B r, M e, and H. The front C atom is single bonded with Ph M e, M e, and H atom.

a. A

Section reference: 20.4

b. B

Section reference: 20.4

c. C

Section reference: 20.4

d. D

Section reference: 20.4

Type: multiple choice question

Title: Chapter 20 Question 23

23) Identify the major elimination product formed under the following conditions:

A chemical reaction shows C H 3 single bond C H 2 single bond C H 2 single bond C (C H 3) (C H 3) single bonded with a six membered C 6 ring under M e O negative and M e O H, gives a product. (A) A chemical structure shows C H 3 single bond C H 2 single bond C H double bond C (C H 3) single bonded with a six membered C 6 ring. (B) A chemical structure shows C H 3 single bond C H 2 single bond C H double bond C (C H 3) single bonded with a six membered C 6 ring. (C) A chemical structure shows C H 3 single bond C H double bond C H single bond C H (C H 3) single bonded with a six membered C 6 ring. (D) A chemical structure shows C H 3 single bond C H 2 single bond C H 2 single bond C (C H 2) single bonded with a six membered C 6 ring.

a. A

Section reference: 20.4

b. B

Section reference: 20.4

Correct/incorrect

c. C

Section reference: 20.4

Correct/incorrect

d. D

Section reference: 20.4

Type: multiple choice question

Title: Chapter 20 Question 24

24) For the reaction shown, which one of the following statements is correct.

A chemical reaction shows a C atom single bonded with n B u, B r, H and M e plus H 2 O under a solvent, gives a C atom is single bonded with n B u, O H, H and M e plus H B r.

a. This is an SN2 reaction which is accelerated in non-polar solvent.

Section reference: 20.3

b. This is an SN2 reaction which is accelerated in polar solvent.

Section reference: 20.3

c. This is an SN1 reaction which is accelerated in non-polar solvent.

Section reference: 20.3

d. This is an SN1 reaction which is accelerated in polar solvent.

Section reference: 20.3

Type: multiple response question

Title: Chapter 20 Question 25

25) Identify the possible products formed in the following substitution reaction. Please select all that apply.

A chemical reaction shows C H 3 single bond C H double bond C H single bond C H 2 single bond C l under K l, gives which product(s) question mark. (A) A chemical structure shows C H 3 single bond C H double bond C H single bond C H 2 single bond I. (B) A chemical structure shows C H 3 single bond C H (I) single bond C H double bond C H 2. (C) A chemical structure shows C H 3 single bond C H (I) single bond C H double bond C H single bond C l. (D) A chemical structure shows C H 3 single bond C H 2 single bond C H double bond C H single bond I.

Section reference: 20.3

a. Product A

b. Product B

c. Product C

d. Product D

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Document Type:
DOCX
Chapter Number:
20
Created Date:
Aug 21, 2025
Chapter Name:
Chapter 20 Halogenoalkanes Substitution And Elimination Reactions
Author:
Andrew Burrows

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