Deck 18: Carboxylic Anhydrides, Esters, and Amides

Question 1

Which of the following compounds is a cyclic ester?

A) 4-butanolactam
B) 2-propylactane
C) 4-butanolactone
D) 2-propylactam

Answer 1

C

Question 2

Which of the following carboxylic derivatives are rarely found in nature?

A) amides
B) anhydrides
C) esters
D) none of these

Answer 2

B

Question 3

Which of the following compounds is a symmetric anhydride?

A)
B)
C)
D)

Answer 3

D

Question 4

Which of the following occurs during the formation of an amide?

A) A carboxylic acid loses its -OH group and an ammonia or an amine loses its -H atom.
B) A carboxylic acid loses its -OH group and an alcohol loses its -H atom.
C) An alcohol loses its -OH group and an ammonia or an amine loses its -H atom.
D) None of these are correct.

Question 5

Identify the IUPAC name of the given compound.

A) propyl ethanoate
B) butyl ethanoate
C) ethyl propanoate
D) ethyl butanoate

Question 6

Which of the following compounds has β-lactam ring in its chemical structure?

A) pyrethrin
B) aspirin
C) amoxicillin
D) ibuprofen

Question 7

What is the minimum number of oxygen atoms present in an ester?

A) 1
B) 2
C) 3
D) 4

Question 8

Which of the following best describes the functional group of anhydrides?

A) two carbonyl groups bonded directly to each other
B) two carboxyl groups bonded directly to each other
C) two carbonyl groups bonded to the same oxygen atom
D) two carboxyl groups bonded to the same oxygen atom

Question 9

What is the IUPAC name of the following compound?

A) butyl butanoate
B) propyl butanoate
C) propanoic anhydride
D) butanoic anhydride

Question 10

Which of the following are anhydrides?

A) only (i) and (ii)
B) only (i) and (iii)
C) only (i) and (iii)
D) (i), (ii) and (iii)

Question 11

Which of the following occurs during an esterification reaction?

A) An alcohol loses its -OH group and a carboxylic acid loses its -H atom.
B) A carboxylic acid loses its -OH group and an alcohol loses its -H atom.
C) A carboxylic acid loses its -OH group and an amine loses its -H atom.
D) A carboxylic acid loses its double-bonded oxygen and an amine loses two hydrogens.

Question 12

Identify a mixed anhydride.

A)
B)
C)
D)

Question 13

What is the minimum number of carbon atoms present in an ester?

A) 1
B) 2
C) 3
D) 4

Question 14

A chemist treats salicylic acid with acetic anhydride to produce a drug. Identify the drug formed by the reaction.

A) naproxen
B) penicillin G
C) salicin
D) aspirin

Question 15

How many atoms are present in the smallest anhydride?

A) 5
B) 7
C) 9
D) 11

Question 16

What is the minimum number of oxygen atoms present in an anhydride?

A) 1
B) 2
C) 3
D) 4

Question 17

What is the IUPAC name of the following compound?

A) ethyl ethanoate
B) methyl ethanoate
C) N-methylacetamide
D) N,N-dimethylacetamide

Question 18

Identify a tertiary amide.

A) N,N-dimethylformamide
B) N-methylacetamide
C) acetamide
D) propanamide

Question 19

What is the common name of the following compound?

A) salicin
B) aspirin
C) adipic acid
D) barbituric acid

Question 20

What is the minimum number of carbon atoms present in an anhydride?

A) 1
B) 2
C) 3
D) 4

Question 21

Which of the following pairs of reactants is best suited for the synthesis of aspirin?

A) salicin and acetic acid
B) salicylic acid and acetic acid
C) salicin and acetic anhydride
D) salicylic acid and acetic anhydride

Question 22

Which pair of reactants forms ethyl butanoate during an esterification reaction?

A) formic acid and 1-butanol
B) butanoic acid and ethanol
C) acetic acid and methanol
D) ethanoic acid and 2-butanol

Question 23

Which ester is formed by the reaction of CH₃CH₂COOH with CH₃CH₂OH?

A) ethyl acetate
B) ethyl propanoate
C) propyl acetate
D) propyl acetate

Question 24

Which of the following statements is true of the structural composition of β-lactam ring?

A) It consists of a seven-membered, aromatic, heterocyclic ester.
B) It consists of a five-membered, aliphatic, heterocyclic ester.
C) It consists of a seven-membered, aromatic, heterocyclic amide.
D) It consists of a four-membered, aliphatic, heterocyclic amide.

Question 25

Which of the following products is formed when acetic acid reacts with propanol?

A) ethyl acetate
B) ethyl propanoate
C) propyl acetate
D) none of these

Question 26

Identify the product formed by the transesterification of the given ester with ethanol.

A) butanoic acid and 1-butanol
B) decanoic acid and ethanol
C) methyl butanoate and 1-butanol
D) ethyl decanoate and methanol

Question 27

Identify the key enzyme involved in the conversion of arachidonic acid to prostaglandins.

A) esterase
B) β-lactamase
C) cyclooxygenase
D) polymerase

Question 28

What is the IUPAC name of a compound with the common name adipamide?

A) hexanediamide
B) benzamide
C) butanamide
D) pentanamide

Question 29

What is the IUPAC name of the following compound?

A) aminopropanoate
B) propanamide
C) butanoylamine
D) butanamide

Question 30

Identify a commonly used catalyst in a Fischer esterification reaction.

A) acetic acid
B) dilute hydrochloric acid
C) dilute carbonic acid
D) concentrated sulfuric acid

Question 31

Which of the following types of compounds are cyclic amides?

A) lactams
B) lactanes
C) lactines
D) lactones

Question 32

Salicin is hydrolyzed in an aqueous acidic solution to form an intermediate. Then, the intermediate is oxidized to form a product. Identify the product formed at the end of the reaction.

A) adipic acid
B) ibuprofen
C) salicylic acid
D) salicylate

Question 33

Which pair of reactants forms butyl formate during an esterification reaction?

A) formic acid and 1-butanol
B) formamide and 1-butanol
C) butanoic acid and ethanol
D) butanamide and methanol

Question 34

Which enantiomer of ibuprofen inhibits cyclooxygenase (COX) activity?

A) (R)-ibuprofen
B) (S)-ibuprofen
C) both (R)-ibuprofen and (S)-ibuprofen
D) none of these

Question 35

What is the common name of the given compound?

A) adipamide
B) benzamide
C) butyramide
D) propanamide

Question 36

Which of the following statements is true of natural pyrethrins?

A) They are esters of chrysanthemic acid.
B) They are amides of permethrin.
C) They are esters of permethrin.
D) They are amides of chrysanthemic acid.

Question 37

Identify the functional group present in natural pyrethrins.

A) amide
B) anhydride
C) ester
D) none of these

Question 38

For which of the following organisms are pyrethrins poisonous?

A) insects
B) mammals
C) plants
D) all of these

Question 39

What is the IUPAC name of the following compound?

A) ethylpropanamide
B) N-ethylpropanamide
C) N-ethylethanamide
D) pentanamide

Question 40

Identify the IUPAC name of the following compound.

A) diamino pentanoate
B) pentanediamine
C) pentanediamide
D) diamidopropane

Question 41

Which of the following products is formed when an ammonium carboxylate salt is heated?

A) an amide
B) an amino acid
C) an amide and an amino acid
D) none of these

Question 42

Which statement about the acid-catalyzed hydrolysis of esters is not true?

A) Using one equivalent of water gives a high yield of products.
B) Using excess water gives a high yield of products.
C) Removing water from the equilibrium mixture gives a high yield of products.
D) All these statements are false.

Question 43

Which of the following compounds is formed by the reaction of formic anhydride with ammonia?

A) formamide
B) N-methylformamide
C) N,N-dimethylformamide
D) acetamide

Question 44

Which of the products is always formed during the hydrolysis of esters, regardless of whether the hydrolysis is carried out in an acidic or a basic solution?

A) an aldehyde
B) a carboxylic acid
C) a salt
D) none of these

Question 45

Which of the following pairs of products is formed when ethyl benzoate is hydrolyzed in an acidic solution?

A) benzoic acid and an ethanoate salt
B) ethanol and a benzoate salt
C) benzoic acid and ethanol
D) benzoic anhydride and methanol

Question 46

Identify the product formed when propanoic anhydride is treated with diethylamine.

A) propanamide
B) N-ethylpropanamide
C) N,N-diethylpropanamide
D) ethyl propanoate

Question 47

Which of the following by-products is obtained when an amine and an anhydride react to form an amide?

A) an alcohol
B) a carboxylic acid
C) water
D) an ester

Question 48

Which of the following statements is true of ester hydrolysis?

A) It occurs rapidly even in cold water.
B) It occurs rapidly at room temperature.
C) It occurs rapidly in boiling water.
D) None of these statements are correct.

Question 49

Which of the following compounds is formed by the reaction of formic anhydride with methylamine?

A) formamide
B) N-methylformamide
C) N,N-dimethylformamide
D) a mixture of two or more of these compounds

Question 50

Which of the following statements is true of a reaction between a low-molecular-weight anhydride and water?

A) The anhydride physically absorbs the water, but no chemical reaction occurs.
B) The anhydride reacts slowly with water to produce two molecules of carboxylic acid.
C) The anhydride reacts readily with water to produce two molecules of carboxylic acid.
D) Whether or not the anhydride reacts with water depends on its molecular weight.

Question 51

Identify the compound obtained when an amine reacts with a carboxylic acid at room temperature.

A) an amide
B) an amino acid
C) an ammonium carboxylate salt
D) none of these

Question 52

Which of the following statements is true of ester hydrolysis?

A) Both an acid and a base can act as the true catalysts of the reaction.
B) Neither an acid nor a base is the true catalyst of the reaction.
C) An acid is a true catalyst, but a base is a reagent and must be present in the appropriate stoichiometric amount.
D) A base is a true catalyst, but an acid is a reagent and must be present in the appropriate stoichiometric amount.

Question 53

Which of the following can be used to mediate the hydrolysis of esters?

A) aqueous sulfuric acid
B) aqueous sodium hydroxide
C) aqueous sulfuric acid and aqueous sodium hydroxide
D) none of these

Question 54

Which of the following compounds would react together at room temperature to form the given compound?

A) hexanamide and 2-propanol
B) hexanoic acid and 2-propanamine
C) 2-propanamine and hexanoic anhydride
D) pentanoic acid and 2-propanamine

Question 55

Which of the products is always formed during the hydrolysis of esters, regardless of whether the hydrolysis is carried out in an acidic or a basic solution?

A) an alcohol
B) carboxylic acid
C) a salt
D) none of these

Question 56

Identify the products formed by the acid-catalyzed hydrolysis of methyl propanoate.

A) methanol and propanoic acid
B) methanol and a propanoate salt
C) propanol and formic acid
D) propanol and a formate salt

Question 57

Which of the following pairs of products is formed by the acid-catalyzed hydrolysis of ethyl formate?

A) ethanol and a formate salt
B) ethanol and formic acid
C) methanol and an ethanoate salt
D) methanol and ethanoic acid

Question 58

Which combination of reactants is commonly used to synthesize amides at room temperature?

A) an amine and an anhydride
B) an amine and an alcohol
C) an amine and a carboxylic acid
D) none of these

Question 59

Which pair of products is formed when ethyl butanoate is hydrolyzed in a basic solution?

A) ethanol and a butanoate salt
B) ethanol and propanoic acid
C) butanol and an acetate salt
D) propanol and acetic acid

Question 60

Predict the products formed in the given reaction.

A) 1-propanol and butanoic acid
B) 1-propanol and sodium butanoate
C) 1-butanol and propanoic acid
D) 1-butanol and sodium propanoate

Question 61

Which of the following statements is true regarding carboxylic anhydrides and phosphoric anhydrides?

A) Both carboxylic anhydrides and phosphoric anhydrides have important biological functions.
B) Neither carboxylic anhydrides nor phosphoric anhydrides have important biological functions.
C) Carboxylic anhydrides are not important in biochemistry, but phosphoric anhydrides are important in biochemistry.
D) Phosphoric anhydrides are not important in biochemistry, but carboxylic anhydrides are important in biochemistry.

Question 62

Which of the following are produced when acetic anhydride reacts with methanol?

A) only propanoic acid
B) only methyl acetate
C) formic acid and methyl acetate
D) acetic acid and methyl acetate

Question 63

Which of the following compounds is formed when an amide reacts with an amine?

A) a carboxylic acid
B) an ester
C) an imide
D) None, amides do not react with amines.

Question 64

Predict the major products of the given reaction.

A)
B)
C)
D)

Question 65

Which of the following gives the correct order of ease of hydrolysis (with easiest to hydrolyze listed first)?

A) anhydrides, esters, amides
B) anhydrides, amides, esters
C) amides, esters, anhydrides
D) amides, anhydrides, esters

Question 66

Which of the following types of compounds is formed when an anhydride reacts with an alcohol?

A) only a carboxylic acid
B) only an ester
C) a carboxylic acid and an ester
D) none of these

Question 67

Identify the products formed when acetamide is hydrolyzed in hydrochloric acid.

A) sodium acetate and acetic acid
B) sodium acetate and ammonia
C) acetic acid and ammonium chloride
D) acetic acid and ammonia

Question 68

Which of the following statements is true of amide hydrolysis?

A) Both an acid and a base can act as the true catalysts of the reaction.
B) Neither an acid nor a base is the true catalyst of the reaction.
C) An acid is a true catalyst, but a base is a reagent and must be present in the appropriate stoichiometric amount.
D) A base is a true catalyst, but an acid is a reagent and must be present in the appropriate stoichiometric amount.

Question 69

Predict the major products of the given reaction.

A)
B)
C)
D)

Question 70

Which pair of products is formed when formic anhydride reacts with ethanol?

A) acetic acid and ethyl formate
B) acetic acid and methyl formate
C) formic acid and methyl formate
D) formic acid and ethyl formate

Question 71

Which of the following statements is true of amide hydrolysis?

A) The reaction is reversible in either an acidic or a basic solution.
B) The reaction is irreversible in both acidic and basic solutions.
C) The reaction is reversible in an acidic solution but irreversible in a basic solution.
D) The reaction is reversible in a basic solution but irreversible in an acidic solution.

Question 72

How many moles of neutral organic compounds will be formed when one mole of the given compound is hydrolyzed in an aqueous solution containing an excess of sodium hydroxide?

A) 1
B) 2
C) 3
D) 4

Question 73

Which types of amines do not react with esters to form amides?

A) 1°
B) 2°
C) 3°
D) All these types of amines react with esters to form amides.

Question 74

Which of the following are the products of the hydrolysis of an amide in a basic solution?

A) a carboxylic acid and an ammonium salt
B) a carboxylic acid and an amine
C) a carboxylate salt and an ammonium salt
D) a carboxylate salt and an amine

Question 75

Which of the following are the products of the hydrolysis of an amide in an acidic solution?

A) a carboxylic acid and an ammonium salt
B) a carboxylic acid and an amine
C) a carboxylate salt and an ammonium salt
D) a carboxylate salt and an amine

Question 76

Which of the following statements is correct about the core ring structure of barbituric acid?

A) It is an aromatic ring that has three carbons and three nitrogens.
B) It is an aromatic ring that has four carbons and two nitrogens.
C) It is an aliphatic ring that has three carbons and three nitrogens.
D) It is an aliphatic ring that has four carbons and two nitrogens.

Question 77

Which of the following types of amines do not react with anhydrides to form amides?

A) 1° amines
B) 2° amines
C) 3° amines
D) All these types of amines react with anhydrides to form amides.

Question 78

Identify the products formed when acetamide is hydrolyzed in sodium hydroxide.

A) sodium acetate and acetic acid
B) sodium acetate and ammonia
C) acetic acid and ammonium chloride
D) acetic acid and ammonia

Question 79

Which of the following statements is true of amide hydrolysis?

A) Amides do not undergo hydrolysis.
B) Amides are more difficult to hydrolyze than esters.
C) Amides and esters are hydrolyzed under similar conditions.
D) Amides are more easily hydrolyzed than esters.

Question 80

What is the correct stoichiometric ratio for the reactants when anhydrides react with amines to form an amide and an ammonium carboxylate salt?

A) one mole of amine for each mole of anhydride
B) one mole of amine for every two moles of anhydride
C) two moles of amine for every mole of anhydride
D) The ratio will depend on the identity of the amine and the anhydride.