Deck 19: Carboxylic Anhydrides, Esters, and Amides

Question 1

Which of the following are anhydrides?

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

Answer 1

B

Question 2

Given the three compounds (i)
Acetic acid
(ii)
Hydroxyacetone
(iii)
Methyl formate
Which are constitutional isomers of one another?

A) only (i) and (ii)
B) only (i) and (iii)
C) only (ii) and (iii)
D) They are all constitutional isomers of one another.

Answer 2

B

Question 3

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

Answer 3

C

Question 4

Methyl acetate is isomeric with which of the following compounds?

A) ethyl formate
B) propanoic acid
C) both a and b
D) neither a nor b

Question 5

Ethyl ethanoate is isomeric with which of the following esters?

A) methyl propanoate
B) propyl formate
C) both a and b
D) neither a nor b

Question 6

Which of the following represents the overall transformation when a carboxylic acid is converted to an amide?

A) The combining of the fragments which remain after the loss of −OH from the carboxylic acid and −H from ammonia or an amine.
B) The combining of the fragments which remain after the loss of −OH from the carboxylic acid and −H from an alcohol.
C) The combining of the fragments which remain after the loss of an oxygen from the carboxylic acid and two hydrogens from ammonia or an amine.
D) none of the above

Question 7

Which of the following represents the overall transformation when a carboxylic acid is converted to an ester?

A) The combining of the fragments which remain after the loss of −OH from the alcohol and −H from the carboxylic acid.
B) The combining of the fragments which remain after the loss of −OH from the carboxylic acid and −H from the alcohol.
C) The combining of the fragments which remain after the loss of −OH from the carboxylic acid and −H from ammonia or an amine.
D) The combining of the fragments which remain after the loss of an oxygen from a carboxyl group and two hydrogens from ammonia or an amine.

Question 8

Ethyl acetate is isomeric with which of the following compounds?

A) methyl propanoate
B) propyl formate
C) butanoic acid
D) all of these

Question 9

What is the IUPAC name for the following compound?

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

Question 10

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

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

Question 11

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

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

Question 12

Given the three compounds (i)
Acetic acid
(ii)
2-hydroxyethanal
(iii)
Methyl formate
Which are constitutional isomers of one another?

A) only (i) and (ii)
B) only (i) and (iii)
C) only (ii) and (iii)
D) They are all constitutional isomers of one another.

Question 13

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

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

Question 14

Which of the following esters does not have an isomeric ester?

A) methyl formate
B) ethyl formate
C) methyl acetate
D) ethyl acetate

Question 15

Which of the following carboxylic derivatives are so reactive that they are rarely found in nature?

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

Question 16

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

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

Question 17

Which of the following is not an isomer of ethyl acetate?

A) methyl propanoate
B) propyl formate
C) butanoic acid
D) None, they are all isomers of ethyl acetate.

Question 18

If the alcohol and acid which react to form an ester are part of the same molecule, the cyclic ester which is formed belongs to which class of compounds?

A) lactams
B) lactanes
C) lactones
D) Esters, there is no special name for these compounds.

Question 19

How many atoms are in the smallest anhydride?

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

Question 20

What is the IUPAC name for the following compound of the following compound?

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

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 of the following pairs of reagents reacts to give an ester which is an isomer of propyl acetate?

A) formic acid + 1-butanol
B) propanoic acid + methanol
C) butanoic acid + ethanol
D) none of these

Question 23

Given the three compounds (i)
Ethyl formate
(ii)
Hydroxyacetone
(iii)
Propanoic acid
Which are constitutional isomers of one another?

A) only (i) and (ii)
B) only (i) and (iii)
C) only (ii) and (iii)
D) They are all constitutional isomers of one another.

Question 24

Cyclic amides are called which of the following?

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

Question 25

Penicillin and many other antibiotics are β-lactams. What is the composition of the β-lactam ring?

A) 1 carbon atom and 3 nitrogen atoms
B) 2 carbon atoms and two nitrogen atoms with the carbon atoms adjacent
C) an alternating sequence of 2 carbon atoms and two nitrogen atoms
D) 3 carbon atoms and one nitrogen atom

Question 26

Which of the following inhibits cyclooxygenase (COX) activity?

A) (R)-ibuprofen
B) (S)-ibuprofen
C) both a and b
D) neither a nor b

Question 27

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

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

Question 28

What is the IUPAC name for the following compound?

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

Question 29

What is the IUPAC name for the following compound?

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

Question 30

Natural pyrethrins contain which of the following functional groups?

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

Question 31

Aspirin was first synthesized near the end of the 19^th century. Chemists in which country first synthesized aspirin?

A) England
B) France
C) Germany
D) the United States

Question 32

Which of the following is commonly used as the catalyst in a Fischer esterification?

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

Question 33

Which of the following statements best describes the natural pyrethrins?

A) They are ester derivatives of chrysanthemic acid.
B) They are amide derivatives of permethrin.
C) They are ester derivatives of permethrin.
D) They are amide derivatives of chrysanthemic acid.

Question 34

Which ester is formed by the reaction of CH₃COOH and CH₃CH₂CH₂OH?

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

Question 35

Natural pyrethrins are toxic to which of the following?

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

Question 36

Which of the following pairs of reagents reacts to give an ester which is an isomer of ethyl acetate?

A) formic acid + 1-butanol
B) propanoic acid + methanol
C) both a and b
D) neither a nor b

Question 37

Which of the following NSAID drugs is not chiral?

A) aspirin
B) ibuprofen
C) naproxen
D) None, they are all chiral.

Question 38

In which year were the penicillins first discovered by Alexander Fleming?

A) 1900
B) 1914
C) 1928
D) 1943

Question 39

Given the three compounds (i)
Acetic acid
(ii)
Ethyl formate
(iii)
Hydroxypropanone
Which are constitutional isomers of one another?

A) only (i) and (ii)
B) only (i) and (iii)
C) only (ii) and (iii)
D) They are all constitutional isomers of one another.

Question 40

What is the IUPAC name for the following compound?

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

Question 41

Which of the following is always a direct product of the hydrolysis of an ester, regardless of whether the reaction is performed under acidic or basic conditions?

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

Question 42

Which of the following compounds would react together at room temperature to form the following 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 43

Which of the following is true when comparing the hydrolysis of esters in acidic solution with the hydrolysis of esters in basic solution?

A) Both the acid and the base are true catalysts of the hydrolysis reaction.
B) Neither the acid nor the base is a true catalyst of the reaction.
C) The acid is a true catalyst, but the base is a reagent and must be present in the appropriate stoichiometric amount.
D) The base is a true catalyst, but the acid is a reagent and must be present in the appropriate stoichiometric amount.

Question 44

Which of the following occurs when water is added to low molecular weight anhydrides?

A) The anhydride physically absorbs the water, but no chemical reaction occurs.
B) The anhydride reacts slowly to produce two molecules of carboxylic acid.
C) The anhydride reacts readily to produce two molecules of carboxylic acid.
D) What happens is highly dependent on the identity of the anhydride.

Question 45

At room temperature, which combination of reactants is commonly used to synthesize amides?

A) an amine and an anhydride
B) an amine and an alcohol
C) an amine and a carboxylic acid
D) None of these, amides cannot be synthesized at room temperature.

Question 46

Which of the following can be formed when the ammonium salt derived from reaction of a carboxylic acid and an amine is heated to a sufficiently high temperature?

A) an amide
B) an amino acid
C) Either a or b, it depends on the identity of the salt.
D) neither a nor b

Question 47

Which of the following is formed by the reaction of propanoic anhydride with diethylamine?

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

Question 48

Which of the following is produced 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 an formate salt

Question 49

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

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 will be formed when an amine and a carboxylic acid react at room temperature?

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

Question 51

Which of the following is produced by the acid-catalyzed hydrolysis of ethyl formate, also known as ethyl methanoate?

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

Question 52

Which of these products would be formed in the following 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 53

Which of the following statements concerning the acid-catalyzed hydrolysis of esters is false?

A) High yields of the hydrolysis products are best achieved in the presence of one equivalent of water.
B) High yields of the hydrolysis products are best achieved in the presence of a large excess of water.
C) High yields of the hydrolysis products are best achieved by removing the water from the equilibrium mixture.
D) All three statements are false.

Question 54

Which is following is true of the hydrolysis of esters?

A) It occurs rapidly, even in cold water.
B) It occurs rapidly in water at room temperature.
C) It occurs rapidly in boiling water.
D) none of the above

Question 55

Which of the following 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 56

Which of the following is always a direct product of the hydrolysis of an ester, regardless of whether the reaction is performed under acidic or basic conditions?

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

Question 57

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

A) aqueous sulfuric acid
B) aqueous sodium hydroxide
C) either a or b
D) neither a nor b

Question 58

Which of the following is produced by hydrolysis of methyl propanoate under basic conditions?

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

Question 59

When an amine reacts with an anhydride to produce an amide, what else is formed?

A) an alcohol
B) a carboxylic acid
C) water
D) No other compound, the amide is the only product.

Question 60

Which of the following is true when comparing the hydrolysis of esters in acidic solution with the hydrolysis of esters in basic solution?

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 when carried out in acidic solution, but is irreversible when carried out in basic solution.
D) The reaction is reversible when carried out in basic solution, but is irreversible when carried out in acidic solution.

Question 61

Which of the following describes the types of compounds produced 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, anhydrides do not react with alcohols.

Question 62

Which of the following 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 63

Which of the following statements is true regarding the hydrolysis of amides?

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

Question 64

What products are obtained when acetamide is hydrolyzed in a solution which contains 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 65

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 66

Anhydrides do not react with which class of amines to form amides?

A) 1°
B) 2°
C) 3°
D) None, anhydrides react with all of these.

Question 67

Which of the following are the products of the hydrolysis of an amide in 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 68

Which of the following are the products of the hydrolysis of an amide in 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 69

What products are obtained when acetamide is hydrolyzed in a solution which contains 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 70

Which of the following is true when comparing the hydrolysis of amides in acidic solution with the hydrolysis of amides in basic solution?

A) Either the acid or base is a true catalyst of the hydrolysis reaction.
B) Neither the acid nor the base is a true catalyst of the reaction.
C) The acid is a true catalyst, but the base is a reagent and must be present in the appropriate stoichiometric amount.
D) The base is a true catalyst, but the acid is a reagent and must be present in the appropriate stoichiometric amount.

Question 71

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

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

Question 72

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

A) a less highly substituted amide
B) a more highly substituted amide
C) an imide
D) Nothing, amides do not react with amines.

Question 73

Which of the following are produced 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 74

Which of the following correctly describes the core ring system found in barbituric acid and all barbiturates?

A) an aromatic ring which has three carbon atoms and three nitrogen atoms
B) an aromatic ring which has four carbon atoms and two nitrogen atoms
C) a non-aromatic ring which has three carbon atoms and three nitrogen atoms
D) a non-aromatic ring which has four carbon atoms and two nitrogen atoms

Question 75

Which of the following is true when comparing the hydrolysis of amides in acidic solution with the hydrolysis of amides in basic solution?

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

Question 76

What is the correct stoichiometric ratio for the reagents 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.

Question 77

Esters do not react with which class of amines to form amides?

A) 1°
B) 2°
C) 3°
D) None, esters react with all of these to form amides.

Question 78

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 79

What are the organic products obtained from the following reaction?

A)
B)
C)
D)

Question 80

What is/are the products formed in the following reaction?

A)
B)
C)
D)