Test Bank Carboxylic Acids, Esters, and Amides Ch17

General, Organic and Biological Chemistry, 4e (Smith)

Chapter 17 Carboxylic Acids, Esters, and Amides

1) Which compound is a secondary amide?

A)

B)

C)

D)

E)

2) What is the IUPAC name of the compound below? 

A) 2-methyl-2-propylpropanoic acid

B) 2-methyl-2-propyl-1-propanoic acid

C) 2,2-dimethylpentanoic acid

D) 2,2-dimethyl-1-pentoic acid

E) 4,4-dimethylpentanoic acid

3) Which statement about the labeled carbons in the compound below is true?

A) C1 is an α carbon and C2 is a β carbon

B) C2 is an α carbon and C1 is a β carbon

C) C3 is an α carbon and C2 is a β carbon

D) C2 is an α carbon and C3 is a β carbon

4) What is the common name of the compound below? 

A) m-bromobenzoic acid

B) 3-bromoacetobenzenoic acid

C) o-bromobenzene carboxylic acid

D) 3-bromo-1-acetobenzoic acid

5) What is the IUPAC name of the compound below?

A) Heptyl propanoate

B) Hexyl propanoate

C) Propyl heptanoate

D) 4-decanoate

E) Propyl hexanoate

6) Which structure properly represents the compound sodium hexanoate?

A)

B)

C)

D)

7) What is the IUPAC name of the compound below? 

A) Propanamide

B) Ethylamide

C) Propanamine

D) N-propylamide

8) What is the IUPAC name of the compound below? 

A) N,N-dimethylpropanamide

B) N,N-dimethylethylamide

C) Dimethylpropanamide

D) Dimethylaminopropanamide

9) What is the structure of 2-chloro-3-hydroxy-4-methylpentanoic acid?

A)

B)

C)

D)

10) What is the structure of 4-ethyl-5-methylheptanoic acid?

A)

B)

C)

D)

11) Which compound has the highest boiling point?

A) (CH3)2CHCH2CHO

B) CH3CH2CH2CH2CH2COOH

C) (CH3)2CHCH2CH2CH2OH

D) CH3(CH2)6CH3

E) All of the compounds have the same boiling point.

12) Which amide has the lowest boiling point?

A) CH3(CH2)5CONH2

B) CH3CH2CON(CH2CH3)2

C) CH3CH2CH2CH2CONHCH2CH3

D) All of the amides have the same boiling point.

13) Which carboxylic acid is responsible for the sting of some types of ants?

A) Formic acid (HCO2H)

B) Hexanoic acid (CH3(CH2)4COOH)

C) Acetic acid (CH3CO2H)

D) Propanoic acid (CH3CH2COOH)

14) Which compound is an a-hydroxy acid?

A)

B)

C)

D)

15) Carboxylic acids react with bases such as NaOH to form what type of compounds?

A) Alcohols

B) Esters

C) Carboxylate salts

D) Carboxylic amides

16) What are the products of the acid–base reaction below?

A)

B)

C)

D) No reaction occurs.

17) Which of the following properly describes soaps?

A) Fatty acids

B) Salts of carboxylic acids that have a long hydrocarbon chain

C) Salts of carboxylic acids that have a short hydrocarbon chain

D) Carboxylic acids

18) What organic product is formed when a carboxylic acid reacts with an alcohol in the presence of sulfuric acid?

A) An ether

B) An ester

C) A ketone

D) An amide

19) Which compound can react with ammonia to produce an amide?

A)

B)

C)

D)

E) More than one of the compounds above can react with ammonia to produce an amide.

20) The reaction of a carboxylic acid (RCOOH) with an alcohol (R'OH) in the presence of an acid catalyst to form an ester (RCOOR') is called which of the following?

A) An addition reaction

B) A Fischer esterification

C) An acid–base reaction

D) A saponification

21) Heating a carboxylic acid with a primary amine forms water along with what organic product?

A) A primary amide

B) A secondary amide

C) A tertiary amide

D) An ester

22) What are the products of the reaction shown? 

A) Hexyl cyclopentanoate + water

B) Cyclopentyl hexanoate + water

C) Pentyl cyclopentanoate + water

D) Cyclopentyl pentanoate + water

23) Which reagent, when reacted with dimethylamine, would produce the compound shown below?

A)

B)

C)

D) N(CH3)3

24) What products are formed in the acid hydrolysis of the ester shown below? 

A) Ethanol and acetic acid

B) Acetic acid and water

C) Propanoic acid and ethanol

D) Acetic acid and ethane

E) Ethanal and ethanol

25) What products are formed in the base hydrolysis of the ester shown below with NaOH?

A) Ethanol and acetic acid

B) Acetic acid and sodium ethoxide

C) Methanol and sodium propanoate

D) Sodium acetate and water

E) Sodium acetate and ethanol

26) What is the hydrolysis reaction of an ester by a base called?

A) An addition reaction

B) A Fischer esterification

C) A substitution reaction

D) A saponification

27) Which compound is a triacylglycerol?

A)

B)

C)

D)

28) Which statement is NOT true?

A) Olestra has properties similar to the triacylglycerols in fats and oils.

B) All natural and synthetic fibers are polymers.

C) Fibers like wool and silk obtained from animals are proteins, and are joined together by many ester linkages.

D) Olestra has so many ester units clustered together that they are too crowded to be hydrolyzed.

29) Which is NOT a polyamide?

A) Kevlar

B) Nylon

C) Olestra

D) N,N-dimethylpropylamide

E) More than one of the compounds is not a polyamide.

30) Which is a lactone?

A)

B)

C)

D)

31) Clavulanic acid (structure shown) is a drug used in conjunction with some antibiotics to overcome certain types of antibiotic resistance. Which of these functional groups is NOT contained in clavulanic acid?

A) Carboxylic acid

B) β-lactam

C) Lactone

D) Ether

32) Aspartame is an artificial sweetener, drawn below. Which of these functional groups is NOT contained in aspartame? 

A) Carboxylic acid

B) Ester

C) Amide

D) Ether

33) Clavulanic acid (structure shown) is a drug used in conjunction with some antibiotics to overcome certain types of antibiotic resistance. How many chirality centers are in clavulanic acid? 

A) 0

B) 1

C) 2

D) 3

E) 4

34) Aspartame is an artificial sweetener, drawn below. How many chirality centers are in aspartame?

A) 0

B) 4

C) 3

D) 1

E) 2

35) Which name is possible for a carboxylic acid?

A) 1-chloropentanoic acid

B) 2-pentylbutanoic acid

C) m-butylbenzoic acid

D) 6,6-dimethylhexanoic acid

36) Which compound is the most soluble in water?

A) (CH3)2CHCH2COOCH3

B) CH3CH2CH2CH2CH2COOH

C) CH3(CH2)6CH3

D) CH3CH2CH2CH2CH2COOK

37) What amide is formed when pentanoic acid is heated with ethylamine?

A)

B)

C)

D)

38) What amide is formed when ethanoic acid (also called acetic acid) is heated with N,N-dimethylamine?

A)

B)

C)

D)

39) Which statement is false?

A) Aspirin is a synthetic compound; that is, it does not occur in nature.

B) The active ingredient in aspirin is acetylsalicylic acid.

C) Salicin, found in willow bark, and salicylic acid, found in meadowsweet blossoms, have structures that are similar to aspirin.

D) Aspirin is a strong acid.

40) Which of these structures represents a soap?

A) CH3CO2– K+

B) CH3(CH2)14CO2– Na+

C) CH3(CH2)12COOH

D) CH3(CH2)7CO2(CH2)7Na

E) More than one of the compounds is a soap.

41) Which statement concerning carboxylic acids is incorrect?

A) The functional group of a carboxylic acid is abbreviated as COOH or CO2H.

B) Carboxylic acids are hydrogen ion donors.

C) The presence of a carboxylic acid increases the [H3O+] in an aqueous solution relative to water.

D) The reaction of a carboxylic acid with a strong base produces a water-insoluble carboxylate salt.

42) At the pH of the aqueous environment in the cells, carboxylic acids exist primarily in their ionized form. Consider the structure of succinic acid, an intermediate in the citric acid cycle. Which of the following properly shows how this carboxylic acid exists in the cell?

A)

B)

C)

D)

43) Which choice represents the products of the acid base reaction shown below:

A)

B)

C)

D)

44) 2-amino-3-methylpentanoic acid (common name isoleucine) is an essential amino acid found in the body's proteins. Which of the following properly represents the structure of this compound?

A)

B)

C)

D)

45) 3-hydroxybutanoic acid is an important starting material for polymer synthesis. Which of the following properly represents the structure of this compound?

A)

B)

C)

D)

46) Methylparaben is an ester used as a preservative in foods, beverages, and cosmetics. It is synthesized in the following reaction. What is the structure of methylparaben?  

A)

B)

C)

D)

47) The organic compound known as aspirin, can be formed in the reaction shown below. Which choice represents the main organic product of this reaction?

A)

B)

C)

D)

48) The drug Clofibrate is used to lower blood triglycerides and cholesterol. It can be made by a Fisher esterification reaction between a carboxylic acid and an alcohol. Which structure represents the alcohol required for its synthesis?

A)

B)

C)

D)

49) The compound shown below is a naturally occurring ester in honey. Which structure represents the carboxylic acid required for its synthesis?

A)

B)

C)

D)

50) The active ingredient in many insect repellants is the amide N,N-diethyl-m-toluamide, also known as DEET. DEET is formed by the reaction between the carboxylic acid and amine shown below. What is the structure of DEET?

A)

B)

C)

D)

51) What is the major organic product of the reaction shown below?

A)

B)

C)

D)

52) Hydrolysis of amides is an important reaction because it represents the first step in the digestion of dietary protein. Which of the following compounds is formed as a result of the hydrolysis of N-methylbutanamide as shown below?

A)

B)

C)

D) NH3

53) Hydrolysis of amides is an important reaction because it represents the first step in the digestion of dietary protein. Which of the following compounds is formed as a result of the hydrolysis of N,N-diethylpropanamide as shown below?

A)

B)

C)

D)

54) Aspirin relieves pain and decreases inflammation because it prevents the synthesis of prostaglandins, the compounds responsible for both of these physiological responses.

55) The compound below is named potassium 2-chloro-3-hydroxybutanoate.

56) The compound below is named sodium 3-hydroxy-5-propylnonanoate.

57) The compound below can hydrogen bond to another molecule like itself. 

58) When soap is mixed with water, the nonpolar hydrocarbon tails dissolve the dirt on the exterior of micelles.

59) To be active, aspirin must cross a cell membrane, and to do so, it must be ionic.

60) A common type of reaction for acyl compounds is substitution.

61) Fischer esterification can be used to synthesize aspirin from salicylic acid.

62) Treatment of an amide (RCONHR') with water in the presence of an acid catalyst (HCl) forms a carboxylic acid with the structure R'COOH, and an amine salt with the structure RNH3+ Cl–.

63) When the compound below reacts with water in the presence of HCl, ethanol and acetic acid are formed.

64) Triacylglycerols are esters formed from glycerol and three acids, each of which has a long carbon chain bonded to the carbonyl group.

65) Animal fats and vegetable oils are composed of triacylglycerols.

66) The first step in the metabolism of a triacylglycerol is hydrolysis of the ester bonds to form glycerol and three fatty acids in a reaction called a simple ester hydrolysis. In the cells of the body, this reaction is catalyzed by acids.

67) All natural and synthetic fibers are polymers.

68) Nylon is an example of a condensation polymer.

69) A condensation polymer is a polymer formed when monomers containing two functional groups come together with the gain of a small molecule such as water.

70) Polyesters are condensation polymers.

71) Penicillin acts as an antibiotic by reacting with an enzyme needed to synthesize the cell nucleus of a bacterium.

72) The ester below contains a propoxy group.

73) The ester below contains a butoxy group. 

74) A lactam can be a primary amide.

75) The compound below is an example of a lactam. 

76) The compound below has the molecular formula C9H11NO, contains a benzene ring, and is a 2° amide.

77) The compound below is a 1° amide.

78) The two compounds below have approximately the same boiling point.

79) The two compounds below have approximately the same boiling point.

80) 2-ethylheptanamide is an alternative name for N-ethylheptanamide.

81) The polyamide product shown is the result of the polymerization reaction between the indicated diacid and amine. 

82) Compounds that contain both a hydroxyl group (OH) and a carboxyl group (COOH) can undergo an intramolecular esterification reaction. The lactone product shown is the result of the intramolecular esterification reaction of the indicated starting material.

83) The following reaction correctly shows the acidic hydrolysis of an amide.

84) The compound 3-chloro-2-hydroxybutanoic acid is an a-hydroxy acid.

85) When a carboxylic acid is dissolved in water, an acid–base equilibrium occurs: the carboxylic acid donates a proton to H2O, forming its conjugate base, a carboxylate anion, and water gains a proton, forming its conjugate acid, H3O+.

86) The salts of carboxylic acids are commonly used as preservatives.

87) The two compounds shown below are formed when N-butylacetamide is hydrolyzed with water in the presence of NaOH.

  and

88) When trimethylamine is heated up with propanoic acid, an amide is formed.

89) The name of the compound below is N-ethylpentanamide. 

90) The name of the compound below is N,N-dipropylbutanamide.

91) Carboxylic acids, esters, and amides are three families of organic molecules that contain a carbonyl group (C=O) bonded to an element more electronegative than carbon.

92) All carbonyl compounds that contain a nitrogen atom are amides.

93) The psychoactive drug benzodiazepine (structure shown) contains two amide groups.

94) (CH3)2CHCHO has a lower boiling point than CH3CH2CH2CH2COOH.

95) Carboxylic acids are capable of hydrogen bonding and often form dimers.

96) (CH3)2CHCH2OH has a lower boiling point than CH3CH2COOH.

97) Tertiary (3°) amides have higher boiling points and melting points than primary (1°) and secondary (2°) amides.

98) A cyclic ester is called a(n) ________.

99) A tertiary amide contains ________ C—N bonds.

100) ________ is the common name of the simplest amide.

101) Carboxylic acids, esters, and amides are called ________ compounds.

102) In a propanoic acid dimer, the two propanoic acid molecules are held together by two ________.

103) When a carboxylic acid is dissolved in water, an acid–base equilibrium occurs: the carboxylic acid donates a proton to H2O, forming its conjugate base, a/an ________, and water gains a proton, forming its conjugate acid, H3O+.

104) Dissolving soap in water forms spherical droplets called ________.

105) The IUPAC name of the compound below is ________. 

106) The IUPAC name of the compound below is ________. 

107) The contents on a bottle of hand lotion list octyl palmitate as an ingredient. Based on its name, the functional group in octyl palmitate is a(n) ________.