Deck 16: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Question 1

Instructions: 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

Answer 1

a lactone

Question 2

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 _____.

A)A
B)B
C)C

Answer 2

B

Question 3

Instructions: 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:

Answer 3

IR spectroscopy would differentiate these two compounds based solely on the nitrile absorption in the first compound and the carbonyl of the N,N- disubstituted of the amide in the second.

Question 4

Instructions: 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 5

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 6

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

Question 7

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 8

What is the correct structure for phenylbenzoate?

A)
B)
C)
D)

Question 9

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 10

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 11

Instructions: 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 12

Instructions: 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 13

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 14

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 15

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 16

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 17

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

Question 18

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 19

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 20

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 21

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

Question 22

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

Question 23

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

A)
B)
C)
D)

Question 24

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 25

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 26

Draw the major product of the following reaction.

Question 27

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 28

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 29

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

Question 30

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 31

Instructions: 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

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 33

Instructions: 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 34

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

Question 35

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 36

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

Question 37

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 38

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

Question 39

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 40

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

A)
B)
C)
D)

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 the lactone product of the following reaction.