Deck 10: Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution Reactions

Question 1

Instructions: Draw structures corresponding to each of the following IUPAC names.
Draw:
prop-2-enenitrile

Answer 1

Question 2

Instructions: Consider the data in the table below to answer the following question(s).
Refer to instructions. Which of the acids in the table has the strongest conjugate base?

Answer 2

CH₃COOH

Question 3

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give the major product(s):

Answer 3

Question 4

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 5

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 6

Instructions: Draw structures corresponding to each of the following IUPAC names.
Draw:
2,5-dihydroxybenzoic acid

Question 7

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give the major product(s):

Question 8

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give the major product(s):

Question 9

What is the order of increasing acidity for the following compounds? (least to most)

A) IV, I, III, II
B) IV, II, III, I
C) II, III, I, IV
D) I, III, II, IV

Question 10

Instructions: Draw structures corresponding to each of the following IUPAC names.
Draw:
2-propylpentanoic acid

Question 11

Instructions: Consider the data in the table below to answer the following question(s).
Refer to instructions. Draw the structure of the strongest acid in the table.

Question 12

Instructions: Draw structures corresponding to each of the following IUPAC names.
Draw:
phenylacetonitrile or phenylethanenitrile

Question 13

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 14

An ether solution contains the following components.
1,2,3,4-tetramethylbenzene benzyl alcohol 2-hydroxybenzoic acid
If this solution is extracted with a 5% solution of NaHCO₃, that is immiscible with ether, which components end up in the ether layer and which in the NaHCO₃ layer?

Question 15

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give the major product(s):

Question 16

Instructions: Consider the data in the table below to answer the following question(s).
Refer to instructions. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly substituted benzoic acid counterparts.

Question 17

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 18

Instructions: Draw structures corresponding to each of the following IUPAC names.
Draw:
cis-cyclopentane-1,3-dicarboxylic acid

Question 19

Instructions: Draw structures corresponding to each of the following IUPAC names.
Draw:
cyanoacetic acid

Question 20

Instructions: Draw structures corresponding to each of the following IUPAC names.
Draw:
N,N-dimethylformamide

Question 21

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

A)
B)
C)
D)

Question 22

Which of the following would represent the correct reaction conditions for the following conversion?

A) 1) KMnO₄, 2) LiAlH₄
B) 1) Mg, ether, 2) CO₂, 3) LiAlH₄
C) 1) NaOH, H₂O, 2) LiAlH₄
D) 1) SOCl₂, benzene, 2) LiAlH₄
E) either b or c

Question 23

Complete the following reaction sequence with the missing major organic products.

Question 24

Which of the following has the highest boiling point?

A) butanoic acid
B) butan-2-ol
C) hexanoic acid
D) heptan-3-one

Question 25

Circle any of the following structures that are not considered to be derivatives of carboxylic acids.

Question 26

Instructions: Consider the information below to answer the following question(s).
The reaction of a carboxylic acid with an alcohol in the presence of acid is termed a Fischer esterification. Refer to instructions. The nucleophile in this reaction is indicated by letter _____.

Question 27

Which of the following does not represent a similarity between nitriles and carboxylic acids?

A) contain 3 carbon bonds to an electronegative element
B) contain two p bonds.
C) act as electrophiles
D) undergo nucleophilic substitution reactions
E) all of these are characteristic of both nitriles and carboxylic acids.

Question 28

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

A)
B)
C)
D)

Question 29

Rank the following compounds in order of increasing reactivity with a nucleophile.

Question 30

Instructions: Provide IUPAC names for the structures in the following question(s).
Name:

Question 31

Instructions: Provide IUPAC names for the structures in the following question(s).
Name:

Question 32

Draw the structure of (Z)-4-methylhex-3-enoic acid.

Question 33

Instructions: Consider the information below to answer the following question(s). The reaction of a carboxylic acid with an alcohol in the presence of acid is termed a Fischer esterification. Refer to instructions. Compound C functions as _____ in this reaction.

A) a base scavenger
B) a solvent
C) a catalyst
D) a neutralizer

Question 34

What is the correct structure for phenylbenzoate?

A)
B)
C)
D)

Question 35

Draw the structure of prop-2-enamide.

Question 36

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A) FCH₂COOH > CH₃COOH > F₂CHCOOH
B) FCH₂COOH > CH₃COOH > CH₃OH
C) CH₃CH₂OH > ClCH₂COOH > BrCH₂COOH
D) CH₃COOH > ClCH₂COOH > CH₃OH

Question 37

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

A)
B)
C)
D)

Question 38

What is the IUPAC name of the following compound?

A) 5,5-dimethyl-5-phenylpentanoic acid
B) 5-methyl-5-phenylhexanoic acid
C) 2,2-dimethylphenylpropanoic acid
D) 5,5-dimethyl-5-phenylbutanal

Question 39

What is the order of decreasing reactivity towards nucleophilic acyl substitution for the carboxylic acid derivatives? (most reactive first)

A) I, II, III, IV
B) I, III, IV, II
C) II, IV, III, I
D) II, I, III, IV

Question 40

Instructions: Consider the information below to answer the following question(s).
The reaction of a carboxylic acid with an alcohol in the presence of acid is termed a Fischer esterification. Refer to instructions. What would be the identity of A, B and C needed to produce the following compound?

Question 41

Draw the major product of the following reaction (which affords a penicillin derivative).

Question 42

Which of the following is the correct order of decreasing reactivity in hydrolysis reactions (more reactive > less reactive)?

A) anhydrides > amides > acid chlorides
B) amides > acid chlorides > anhydrides
C) anhydrides > acid chlorides > amides
D) acid chlorides > anhydrides > amides

Question 43

Instructions: Provide the missing structure(s) or reagent(s) for each reaction or sequences of reactions. Show all relevant stereochemistry.
Provide missing structure(s):

Question 44

Draw the structure of polymer formed in the following reaction. Show only a single monomer.

Question 45

What is the IUPAC name of the following compound?

A) dimethylamino 3-phenylpropanoic acid
B) N,N-dimethyl 2-phenylethyl amide
C) N,N-dimethyl 3-phenylpropanamide
D) dimethyl 2-phenylpropanoylamine

Question 46

Draw the structure of polymer formed in the following reaction. Show only a single monomer.

Question 47

Instructions: Provide the missing structure(s) or reagent(s) for each reaction or sequences of reactions. Show all relevant stereochemistry.
Provide missing structure(s):

Question 48

What is the major organic product produced by the following reaction?

A)
B)
C)
D)

Question 49

Instructions: Provide the missing structure(s) or reagent(s) for each reaction or sequences of reactions. Show all relevant stereochemistry.
Provide missing structure(s):

Question 50

Which of the following compounds is a 2 $\degree$ amide?

A)
B)
C)
D)

Question 51

Which of the following best describes the key mechanistic steps in the reaction of an acid chloride and an alcohol to form an ester?

A) elimination followed by addition
B) addition followed by decarboxylation
C) addition followed by elimination
D) substitution followed by addition

Question 52

Draw the major product of the following reaction.

Question 53

What is the major organic product produced by the following reaction?

Question 54

What is the correct assignment of the functional groups in the following compounds?

A) 1 = acid chloride; 2 = ester; 3 = nitrile
B) 1 = carboxylic acid; 2 = ester; 3 = imide
C) 1 = acid chloride; 2 = ester; 3 = amide
D) 1 = acid anhydride; 2 = ester; 3 = imide

Question 55

Draw the major products of the following biochemical reaction (where R = a fatty acid chain).

Question 56

Instructions: Provide the missing structure(s) or reagent(s) for each reaction or sequences of reactions. Show all relevant stereochemistry.
Provide missing structure(s):

Question 57

The product of the following reaction is a primary essence contained within bananas.

Question 58

Instructions: Provide the missing structure(s) or reagent(s) for each reaction or sequences of reactions. Show all relevant stereochemistry.
Provide missing structure(s):

Question 59

Instructions: Provide the missing structure(s) or reagent(s) for each reaction or sequences of reactions. Show all relevant stereochemistry.
Provide missing structure(s):

Question 60

Rank the following from highest to lowest reactivity toward reaction with EtOH.

Question 61

Write the complete stepwise mechanism for the basic hydrolysis of acetamide, shown below. Show all electron flow with arrows and draw all intermediate structures.

Question 62

Choose the best reagent(s) for carrying out the following conversion.

Question 63

Choose the best reagent(s) for carrying out the following conversion.

Question 64

Choose the best reagent(s) for carrying out the following conversion.

Question 65

Ethyl phenylacetate is a pleasant smelling compound used in perfumery. Draw structures for each of the intermediates in the synthesis of ethyl phenylacetate below.

Question 66

Choose the best reagent(s) for carrying out the following conversion.