Chapter 24 Acyl Substitution Reactions Complete Test Bank - Chemistry 3 4e | Test Bank Burrows by Andrew Burrows. DOCX document preview.

Chapter 24 Acyl Substitution Reactions Complete Test Bank

Chapter 24: Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution and α-Substitution Reactions

Test Bank

Type: matching question

Title: Chapter 24 Question 01

1) Rank the following molecules, A-D, in order of their relative electrophilicity (where 1 is the most electrophilic and 4 is the least electrophilic):

(A) A chemical structure shows C single bonded with P h and N M e 2, and double bonded with an O atom.

(B) A chemical structure shows C single bonded with P h and C l, and double bonded with an O atom.

(C) A chemical structure shows C single bonded with P h and O M e, and double bonded with an O atom.

(D) A chemical structure shows C single bonded with P h and M e, and double bonded with an O atom.

Section reference: 24.1

a. 1 = Molecule B

b. 2 = Molecule D

c. 3 = Molecule C

d. 4 = Molecule A

Type: matching question

Title: Chapter 24 Question 02

2) Rank the following molecules, A-D, in order of their relative acidity (where 1 is the most acidic and 4 is the least acidic):

(A) A chemical structure shows C single bonded with C H 3 and O C H 3, and double bonded with an O atom.

(B) A chemical structure shows C single bonded with C H 3 and O H, and double bonded with an O atom.

(C) A chemical structure shows C single bonded with C H 3 and H, and double bonded with an O atom.

(D) A chemical structure shows C single bonded with two C H 3 molecules, and double bonded with an O atom.

Section reference: 24.1

a. 1 = Molecule B

b. 2 = Molecule C

c. 3 = Molecule D

d. 4 = Molecule A

Type: multiple choice question

Title: Chapter 24 Question 03

3) For the following reaction, pick out a suitable rate profile from A-D for this transformation:

A chemical reaction shows C single bonded with P h and C l, and double bonded with an O atom, under N a O M e, gives C single bonded with P h and O M e and double bonded with an O atom, plus N a C l.

(A) A coordinate plane relates Gibbs energy, G to Progress of reaction, where Progress of reaction is drawn along the horizontal axis. A curve is drawn in the first quadrant, which starts from closer to the G axis, goes parallel to the horizontal axis, rises upward, attains a maxima point, dips steeply, goes horizontally to the right, and exits the right viewing window.

(B) A coordinate plane relates Gibbs energy, G to Progress of reaction, where Progress of reaction is drawn along the horizontal axis. A curve is drawn in the first quadrant, which starts from closer to the G axis, goes parallel to the horizontal axis, dips concavely upward, attains minima point, goes horizontally to the right, dips concavely downward, goes horizontally to the right, and exits the right viewing window.

(C) A coordinate plane relates Gibbs energy, G to Progress of reaction, where Progress of reaction is drawn along the horizontal axis. A curve is drawn in the first quadrant, which starts from closer to the G axis, goes parallel to the horizontal axis, rises concavely downward, attains a maxima point, dips steeply, attains minima point, rises concavely downward, dips steeply, goes horizontally to the right, and exits the right viewing window. The first maxima point is higher than the second maxima point.

(D) A coordinate plane relates Gibbs energy, G to Progress of reaction, where Progress of reaction is drawn along the horizontal axis. A curve is drawn in the first quadrant, which starts from closer to the G axis, goes parallel to the horizontal axis, rises concavely downward, attains a maxima point, dips steeply, attains minima point, rises concavely downward, dips steeply, goes horizontally to the right, and exits the right viewing window. The first maxima point is lower than the second maxima point.

a. A

Section reference: 24.1

b. B

Section reference: 24.1

c. C

Section reference: 24.1

d. D

Section reference: 24.1

Type: multiple response question

Title: Chapter 24 Question 04

4) For the following reaction, pick out the products. Please select all that apply.

A chemical reaction shows C H 3 single bond C O single bond O single bond C O single bond C (C H 3) 3, under N H 3 gives a product.
(A) A chemical structure shows C single bonded with C H 3 and N H 2, and double bonded with an O atom.

(B) A chemical structure shows C double bonded with an O atom, and single bonded with N H 2, and a C atom, where C is single bonded with three C H 3 molecules.

(C) A chemical structure shows C H 3 single bond C O single bond N H single bond C O single bond C, where C is single bonded with three C H 3 molecules.

(D) A chemical structure shows C single bonded with C H 3 and O H, and double bonded with an O atom.

(E) A chemical structure shows C double bonded with an O atom, and single bonded with O H, and a C atom, where C is single bonded with three C H 3 molecules.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

e. E

Section reference: 24.2

Type: multiple response question

Title: Chapter 24 Question 05

5) From the following reactions, A-D, pick out those which lead to the formation of ethyl acetate (ethyl ethanoate). Please select all that apply.

A chemical structure of Ethyl acetate or ethyl ethanoate shows C single bonded with C H 3 and E t O, and double bonded with an O atom.

(A) A chemical reaction shows C H 3 single bond C H 2 single bond O H, plus C single bonded with C l and C H 3, and double bonded with an O atom, under E t 3 N and C H 2 C l 2 it gives a product.

(B) A chemical reaction shows C H 3 single bond C H 2 single bond C l, plus C single bonded with N a O and C H 3, and double bonded with an O atom, under C H 2 C l 2 it gives a product.

(C) A chemical reaction shows C H 3 single bond C H 2 single bond O H, plus C H 3 single bond C O single bond O single bond C O single bond C H 3, under E t 3 N and C H 2 C l 2 it gives a product.

(D) A chemical reaction shows C single bonded with O H and C H 3, and double bonded with an O atom, under E t O H and H C l it gives a product.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

Type: multiple choice question

Title: Chapter 24 Question 06

6) For the following transformation, deduce whether it is an oxidation, reduction or neither:

A chemical reaction shows M e single bond C O single bond O single bond C O single bond P h, gives C single bonded with M e and O H, and double bonded with an O atom.

a. Oxidation

Section reference: 24.2

b. Reduction

Section reference: 24.2

c. Neither

Section reference: 24.2

Type: matching question

Title: Chapter 24 Question 07

7) Rank the following molecules, A-D, in order of their ability to form enols (with 1 being most able and 4 the least able):

(A) A chemical structure shows C single bonded with M e O and H, and double bonded with an O atom.

(B) A chemical structure shows M e single bond C O single bond C H 2 single bond C O single bond O M e.

(C) A chemical structure shows C single bonded with M e and O M e, and double bonded with an O atom.

(D) A chemical structure shows C single bonded with two M e, and double bonded with an O atom.

Section reference: 24.3

a. 1 = Molecule B

b. 2 = Molecule D

c. 3 = Molecule C

d. 4 = Molecule A

Type: multiple choice question

Title: Chapter 24 Question 08

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

A chemical reaction shows C single bonded with P h and O H, and double bonded with an O atom, under H C l catalytic and H 2 superscript 18 end superscript O solvent gives a product.

(A) A chemical structure shows C single bonded with P h and C l, and double bonded with an O atom.
A chemical structure shows C single bonded with superscript 18 end superscript O H, two O H molecules, and P h.

(B) A chemical structure shows C single bonded with superscript 18 end superscript O H, O superscript 18 end superscript H, and P h.

(C) A chemical structure shows C single bonded with superscript 18 end superscript O, O H, and P h.

(D) A chemical structure shows C single bonded with superscript 18 end superscript O, O superscript 18 end superscript H, and P h.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

e. E

Section reference: 24.2

Type: multiple response question

Title: Chapter 24 Question 09

9) For the following reaction, pick out the product:

A chemical reaction shows C H 3 single bond C H 2 single bond C H (C H 3) single bond C O single bond O single bond C H (C H 3) single bond C H 3, under L i A l H 4 and H 2 O it gives a product.

(A) A chemical structure shows C H 3 single bond C H 2 single bond C H (C H 3) single bond C H (O H) single bond O C H 3.

(B) A chemical structure shows C H 3 single bond C H 2 single bond C H (C H 3) single bond C H 2 single bond O H.

(C) A chemical structure shows C single bonded with two C H 3 molecules and O H.

(D) A chemical structure shows C H 3 single bond C H 2 single bond C H (C H 3) single bond C O single bond O H.

(E) A chemical structure shows C H 3 single bond C H 2 single bond C H (C H 3) single bond C H (O H) single bond O single bond C H (C H 3) single bond C H 3.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

e. E

Section reference: 24.2

Type: multiple choice question

Title: Chapter 24 Question 10

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

A chemical reaction shows B u b r, under 1. M g, E t 2 O, 2. C O 2, and 3. H C l, H 2 O gives a product.

(A) A chemical structure shows C single bonded with C l and B u, and double bonded with an O atom.

(B) A chemical structure shows C single bonded with O H and B u, and double bonded with an O atom.

(C) A chemical structure shows C single bonded with H and B u, and double bonded with an O atom.

(D) A chemical structure shows C single bonded with two H atoms, B u, and O H.

(E) A chemical structure shows C single bonded with two H atoms, Bu, and C l.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

e. E

Section reference: 24.2

Type: multiple response question

Title: Chapter 24 Question 11

11) For the following reactions, A-D, pick out those which lead to the formation of 2-methyl-2-phenylethanol. Please select all that apply.

A chemical structure of 2 Methyl 2 phenylethanol shows C single bonded with two C H 3 molecules, O H, and P h.

(A) A chemical reaction shows C single bonded with P h and C l, and double bonded with an O atom, under excess C H 3 M g B r and H positive it gives a product.

(B) A chemical reaction shows C single bonded with P h and O C H 3, and double bonded with an O atom, under excess C H 3 M g B r and H positive it gives a product.

(C) A chemical reaction shows C single bonded with P h and O H, and double bonded with an O atom, under excess C H 3 M g B r and H positive it gives a product.

(D) A chemical reaction shows C single bonded with P h and C H 3, and double bonded with an O atom, under C H 3 M g B r and H positive it gives a product.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

Type: multiple choice question

Title: Chapter 24 Question 12

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

A chemical reaction shows P h M g B r under 1. C H 3 C N and 2. H C l, H 2 O it gives a product.

(A) A chemical structure shows C single bonded with P h and C H 3, and double bonded with an O atom.

(B) A chemical structure shows C single bonded with P h and C H 3, and double bonded with an N H atom.

(C) A chemical structure shows C single bonded with P h, C H 3, N H 2, and O H.

(D) A chemical structure shows P h single bond N double bond C H single bond C H 3.

(E) A chemical structure shows P h single bonded with N H 2.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

e. E

Section reference: 24.2

Type: multiple response question

Title: Chapter 24 Question 13

13) Which of the following reagents, A-E, are suitable reagents for the following transformation? Please select all that apply.

A chemical reaction shows C single bonded with H e x and O H, and double bonded with an O atom, gives C single bonded with H e x and C l, and double bonded with an O atom.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

e. E

Section reference: 24.2

Type: multiple choice question

Title: Chapter 24 Question 14

14) Which of the following reagents, A-D, is a suitable reagent for the following transformation?

A chemical reaction shows C single bonded with P h and C l, and double bonded with an O atom, gives C single bonded with P h and H, and double bonded with an O atom.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

Type: multiple choice question

Title: Chapter 24 Question 15

15) Which of the following reagents, A-E, is a suitable reagent for the following transformation?

A chemical reaction shows P h single bond C H 2 single bond O H, gives C single bonded with P h and O H, and double bonded with an O atom.

a. A

Section reference: 24.2, 23.2

b. B

Section reference: 24.2, 23.2

c. C

Section reference: 24.2, 23.2

d. D

Section reference: 24.2, 23.2

e. E

Section reference: 24.2, 23.2

Type: multiple choice question

Title: Chapter 24 Question 16

16) Which of the following reagents, A-E, is a suitable reagent for the following transformation?

A chemical reaction shows C single bonded with P h and M e, and double bonded with an O atom, gives C single bonded with P h and O H, and double bonded with an O atom.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

e. E

Section reference: 24.2

Type: multiple choice question

Title: Chapter 24 Question 17

17) From the following equilibrium, pick out the approximate equilibrium constant for this process:

A chemical reaction shows C single bonded with C H 3 and O E t, and double bonded with an O atom with p K subscript a end subscript equals 25, plus N a O E t, is equivalent to C single bonded with O N a and O E t, and double bonded with C H 2 molecule, plus H O E t with p K subscript a end subscript equals 16.

a. 10-0.64

Section reference: 24.3

b. 10-1.56

Section reference: 24.3

c. 10-9

Section reference: 24.3

d. 10-12

Section reference: 24.3

e. 10-16

Section reference: 24.3

Type: matching question

Title: Chapter 24 Question 18

18) Rank the following molecules, A-D, in order of their relative acidity (where 1 is the most acidic and 4 is the least acidic):

(A) A chemical structure shows C single bonded with C H 3 and N M e 2, and double bonded with an O atom.

(B) A chemical structure shows C single bonded with C H 3 and C l, and double bonded with an O atom.

(C) A chemical structure shows C single bonded with C H 3 and O M e, and double bonded with an O atom.

(D) A chemical structure shows C H 3 single bond C O single bond O single bond C O single bond P h.

Section reference: 24.3

a. 1 = Molecule B

b. 2 = Molecule D

c. 3 = Molecule C

d. 4 = Molecule A

Type: multiple choice question

Title: Chapter 24 Question 19

19) For the following Claisen reaction, pick out the product:

A chemical reaction shows C H 3 single bond C H 2 single bond C O single bond O E t, under N a O E t and E t O H gives a product.

(A) A chemical structure shows C H 3 single bond C H 2 single bond C O single bond C H (C H 3) single bond C O single bond O E t.

(B) A chemical structure shows C H 3 single bond C H 2 single bond C (O N a) double bond C (C H 3) single bond C O single bond O E t.

(C) A chemical structure shows C H 3 single bond C H (E t) single bond C O single bond O E t.

(D) A chemical structure shows C single bonded with two O E t and double bonded with an O atom.

(E) A chemical structure shows C H 3 single bond C H 2 single bond C O single bond O single bond C O single bond C H 2 single bond C H 3.

a. A

Section reference: 24.3

b. B

Section reference: 24.3

c. C

Section reference: 24.3

d. D

Section reference: 24.3

e. E

Section reference: 24.3

Type: multiple choice question

Title: Chapter 24 Question 20

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

A chemical reaction shows C single bonded with P h and C H 3, and double bonded with an O atom, plus C single bonded with C H 3 and O E t, and double bonded with an O atom, under 1. N a O E t, E t O H and 2. H C l, H 2 O gives a product.

(A) A chemical structure shows P h single bond C O single bond C O single bond C H 3.

(B) A chemical structure shows P h single bond C O single bond C H 2 single bond C O single bond C H 3.

(C) A chemical structure shows P h single bond C O single bond C H 2 single bond C O single bond O E t.

(D) A chemical structure shows P h single bond C O single bond C H double bond C (C H 3) single bond P h.

(E) A chemical structure shows C H 3 single bond C O single bond C H 2 single bond C O single bond O E t.

a. A

Section reference: 24.3

b. B

Section reference: 24.3

c. C

Section reference: 24.3

d. D

Section reference: 24.3

e. E

Section reference: 24.3

Type: multiple choice question

Title: Chapter 24 Question 21

21) Identify the reaction class for the following reaction:

A chemical reaction shows C single bonded with R and O R prime groups, and double bonded with an O atom, plus N u H, gives C single bonded with R and N u, and double bonded with an O atom, plus H O R prime.

a. Nucleophilic acyl substitution

Section reference: 24.1

b. α-substitution

Section reference: 24.1

c. carbonyl-carbonyl condensation

Section reference: 24.1

d. nucleophilic alkyl substitution

Section reference: 24.1

Type: multiple response question

Title: Chapter 24 Question 22

22) A Dieckmann reaction is an example of what type of process? Please select all that apply.

Section reference: 24.3

a. Saponification reaction

b. Claisen condensation reaction

c. An intramolecular reaction

d. SN2 reaction

Type: multiple response question

Title: Chapter 24 Question 23

23) How can the formation of ethyl butanoate from butanoic acid and ethanol be favoured? Please select all that apply.

A chemical reaction shows C H 3 single bond C H 2 single bond C H 2 single bond C O single bond O H, plus O H single bond C H 2 single bond C H 3, under H positive it gives C H 3 single bond C H 2 single bond C H 2 single bond C O single bond O single bond C H 2 single bond C H 3, plus H 2 O.

Section reference: 24.2

a. Add a drying agent (e.g. molecular sieves) b. Distillation (e.g. using a Dean-Stark trap) c. Lower reaction temperature (e.g. ice bath) d. Use water as a solvent

e. Use ethanol as a solvent

Type: multiple choice question

Title: Chapter 24 Question 24

24) Predict the major product of the following reaction, at room temperature.

A chemical reaction shows C H 3 single bond C H 2 single bond C O 2 single bond O H, plus N H 2 single bond C H 2 single bond C H 2 single bond C H 3, under room temperature, it is equivalent to product question mark.

(A) A chemical structure shows C H 3 single bond C H 2 single bond C O single bond N H single bond C H 2 single bond C H 2 single bond C H 3.

(B) A chemical structure shows C H 3 single bond C H 2 single bond C (O H) 2 single bond N H single bond C H 2 single bond C H 2 single bond C H 3.

(C) A chemical structure shows C H 3 single bond C H 2 single bond C O single bond O negative N positive H 3 single bond C H 2 single bond C H 2 single bond C H 3.

(D) A chemical structure shows C H 3 single bond C H 2 single bond C H 2 single bond N, where N single bonded with two C O C H 3 molecules.

a. A

Section reference: 24.2

b. B

Section reference: 24.2

c. C

Section reference: 24.2

d. D

Section reference: 24.2

Type: multiple choice question

Title: Chapter 24 Question 25

25) Identify the major enol of methyl 3-oxopentanoate.

(A) A chemical structure shows C H 3 single bond C H 2 single bond C O single bond C H 2 single bond C O negative double bond O single bond C H 3.

(B) A chemical structure shows C H 3 single bond C H double bond C O H single bond C H 2 single bond C O single bond O single bond C H 3.

(C) A chemical structure shows C H 3 single bond C H 2 single bond C O single bond C H double bond C O H single bond O single bond C H 3.

(D) A chemical structure shows C H 3 single bond C H 2 single bond C O H double bond C H single bond C O single bond O single bond C H 3.

a. A

Section reference: 24.3

b. B

Section reference: 24.3

c. C

Section reference: 24.3

d. D

Section reference: 24.3

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Document Type:
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Chapter Number:
24
Created Date:
Aug 21, 2025
Chapter Name:
Chapter 24 Acyl Substitution Reactions
Author:
Andrew Burrows

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