Deck 16: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Question 1

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

Answer 1

I, III, IV, II

Question 2

What is the correct structure for phenylbenzoate?

A)

B)

C)

D)

Answer 2

Question 3

Draw the structure of prop-2-enamide.

Answer 3

Question 4

Consider the reaction below to answer the following question(s).
Refer to instructions. The purpose of the base catalyst in this reaction is:

A) to polarize the carbonyl group to make it more electrophilic
B) to convert the ester to an intermediate carboxylic acid
C) to convert the alcohol group to an alkoxide anion, which is a better nucleophile
D) all of these

Question 5

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 6

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 _____.

A)A
B)B
C)C

Question 7

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 8

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

Question 9

Of the following, which represents a possible direct conversion of the reactant to product shown?

A) ester to acid chloride
B) thioester to acid anhydride
C) ester to amide
D) acid anhydride to acid chloride

Question 10

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

Question 11

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

Question 12

Consider the reaction below to answer the following question(s).
Refer to instructions. The product of this reaction is:

A) a lactone
B) an anhydride
C) a lactam
D) an ether

Question 13

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

Question 14

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

Question 15

Consider the reaction below to answer the following question(s).
Refer to instructions. Write the complete stepwise mechanism for this reaction. Show intermediate structures and all electron flow with arrows.

Question 16

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

Question 17

Consider the reaction below to answer the following question(s).
Refer to instructions. This reaction is an example of:

A) an intermolecular nucleophilic acyl substitution reaction
B) an intramolecular nucleophilic acyl substitution reaction
C) an intermolecular S_N2 reaction
D) an intramolecular S_N2 reaction

Question 18

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

Question 19

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

Question 20

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

Question 21

Tell which spectroscopic technique you would use to distinguish between the two members of the pair. Tell what differences you would expect to see.
Identify spectroscopic technique:

Question 22

Which of the following compounds is a 2° amide?

A)

B)

C)

D)

Question 23

The product of the following reaction is a primary essence contained within bananas. a)Draw its structure.
b)The product of the above reaction could also be produced by the reaction of an acid and an alcohol. Draw their structures.

Question 24

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

Question 25

Tell which spectroscopic technique you would use to distinguish between the two members of the pair. Tell what differences you would expect to see.
Identify spectroscopic technique:

Question 26

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

Question 27

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 28

Draw the major product of the following reaction.

Question 29

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

A)

B)

C)

D)

Question 30

Which of the following is the correct assignment of the classes of the following compounds?

A) 1 = lactone; 2 = ester; 3 = amide
B) 1 = ester; 2 = ester; 3 = imide
C) 1 = ester; 2 = imide; 3 = amide
D) 1 = lactone; 2 = anhydride; 3 = imide

Question 31

Tell which spectroscopic technique you would use to distinguish between the two members of the pair. Tell what differences you would expect to see.
Identify spectroscopic technique:

Question 32

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

Question 33

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

Question 34

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

Question 35

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

A) 1 > 2 > 3
B) 2 > 3 > 1
C) 1 > 3 > 2
D) 3 > 2 > 1

Question 36

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 37

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 38

What is the correct assignment of the names of the following substituted benzenes?

A) 1 = benzoyl chloride; 2 = benzyl amine; 3 = benzyl alcohol
B) 1 = benzyl amine; 2 = benzoyl chloride; 3 = benzamide
C) 1 = benzamide; 2 = benzoyl chloride; 3 = benzoic acid
D) 1 = benzoyl chloride; 2 = benzamide; 3 = benzoic acid

Question 39

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

Question 40

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 41

The two spectra below belong to acetic acid (ethanoic acid) and its isomer, methyl formate (methyl methanoate). Which spectrum corresponds to which compound? Explain your answer. (Spectra obtained from SDBSWeb: http://www.aist.go.jp/RIODB/SDBS)

Question 42

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

Question 43

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

Question 44

Draw the structure of the lactone product of the following reaction.

Question 45

The following a monomer of the polymer used in biodegradable sutures called Lactomerâ. Upon hydrolysis what product(s) form(s)? Draw the appropriate structure(s).

Question 46

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