Deck 17: Carboxylic Acids and Their Derivatives

Question 1

The pleasant,characteristic odor of fruit flavorings is often associated with the presence of

A)esters
B)carboxylic acids
C)carboxylate salts
D)ketones

Answer 1

esters

Question 2

Which functional group contains a carbonyl group and a hydroxyl group bonded to the same carbon atom?

A)aldehyde
B)amide
C)carboxylic acid
D)ester
E)ketone

Answer 2

carboxylic acid

Question 3

The similarities in properties of carboxylic acids,esters,and amides can best be explained by

A)their polarity and structural similarities.
B)their similarities in molar mass.
C)hydrogen bonding.
D)the ease with which they form ions.
E)none of these.

Answer 3

their polarity and structural similarities.

Question 4

Which acid would be expected to have the lowest boiling point?

A)acetic,CH₃CO₂H
B)benzoic,C₆H₅CO₂H
C)formic,HCO₂H
D)oxalic, (CO₂H)₂
E)stearic,CH₃(CH₂)₁₆CO₂H

Question 5

What is the IUPAC name of the compound shown?

A)1-butanoic acid
B)4-butanoic acid
C)1-butenoic acid
D)3-butenoic acid
E)none of the above

Question 6

Which of the following has the highest boiling point?

A)ethane,CH₃CH₃
B)dimethyl ketone,CH₃COCH₃
C)ethyl alcohol,CH₃CH₂OH
D)acetic acid,CH₃COOH
E)formaldehyde,HCHO

Question 7

Which molecule is a carboxylic acid?

A)

B)

C)

D)

E)CH₃CH₂CH₂NH₂

Question 8

Which molecule is an amide?

A)

B)

C)

D)

E)CH₃CH₂CH₂NH₂

Question 9

Which compound is a carboxylic acid?

A)CH₃COO^-K⁺
B)CH₃COOH
C)(CH₃)₂CHOOCH₃
D)(CH₃CO)₂O
E)(CH₃)₂O

Question 10

Which molecule is an ester?

A)

B)

C)

D)

E)CH₃CH₂CH₂NH₂

Question 11

All of the statements concerning citric acid are true except

A)it contains three carboxylic acid groups because its carbon skeleton is branched.
B)it is very soluble in water.
C)its salts are used in many consumer products.
D)it is produced only by plants.
E)it is a weak acid.

Question 12

What is the IUPAC name of the compound shown?

A)3-hexanoic acid
B)2-ethyl pentanoate
C)2-ethylpentanoic acid
D)3-heptanoic acid
E)4-heptanoic acid

Question 13

Which acid would be expected to have the highest boiling point?

A)acetic,CH₃CO₂H
B)benzoic,C₆H₅CO₂H
C)formic,HCO₂H
D)oxalic, (CO₂H)₂
E)stearic,CH₃(CH₂)₁₆ CO₂H

Question 14

Which functional group contains a carbonyl group and an ether linkage bonded to the same carbon atom?

A)aldehyde
B)amide
C)carboxylic acid
D)ester
E)ketone

Question 15

Which of the following bonds is not present in a carboxylic acid functional group?

A)C=C
B)C=O
C)C-O
D)O-H
E)none of the above

Question 16

What is the common name of the molecule shown?

A)γ-amino-α-hydroxybutyric acid
B)4-amino-2-hydroxybutanoic acid
C)α-amino-γ-hydroxybutyric acid
D)1-amino-3-hydroxybutanoic acid
E)none of these

Question 17

Which molecule shown is β-hydroxy butyric acid?

A)

B)

C)

D)

E)

Question 18

The most common reactions of carboxylic acids or their derivatives involve

A)addition across the double bond between carbon and oxygen.
B)replacement of the oxygen atom in the carbonyl group.
C)replacement of the group bonded to the carbonyl atom.
D)oxidation of the R group.
E)reduction of the R group.

Question 19

All of the statements about carboxylic acids are true except

A)they undergo substitution reactions involving the -OH group.
B)at low molecular weights they are liquids with sharp stinging odors.
C)they form hydrogen bonds,causing their boiling points to be higher than expected on the basis of molecular weight.
D)they react with bases to form salts which are often more soluble than the original acid.
E)when they behave as acids,the -OH group is lost leaving the CO^- ion.

Question 20

Which molecule is formic acid?

A)

B)

C)

D)

E)

Question 21

Carboxylic acids generally taste ________.

A)sour
B)sweet
C)bitter
D)salty
E)spicy

Question 22

What is the IUPAC name of the molecule shown?

A)ethyl butanoate
B)butyl ethanoate
C)acetyl butyrate
D)butyl acetate
E)2-hexanoic ester

Question 23

Which acid would be expected to have the lowest boiling point?

A)acetic
B)benzoic
C)formic
D)oxalic
E)stearic

Question 24

What is the IUPAC name of the compound shown?

A)1-methylpropanamide
B)N-methylpropanamide
C)N-butylethanamide
D)N-methylbutanamide
E)N-butylformamide

Question 25

What is the IUPAC name of the molecule shown?

A)γ-amino-α-hydroxybutyric acid
B)4-amino-2-hydroxybutanoic acid
C)α-amino-γ-hydroxybutyric acid
D)1-amino-3-hydroxybutanoic acid
E)none of these

Question 26

An acyl group is a group in which

A)an amine and a carbonyl are bonded to the same carbon atom.
B)a hydroxyl and an alkene are bonded to the same carbon atom.
C)an alpha carbon is bonded to an alkyl group.
D)an alkyl group is bonded to a carbonyl carbon atom.
E)an acidic group is bonded to an aromatic group.

Question 27

Which of the compounds shown can form hydrogen bonds with other identical molecules? Explain each case.

Question 28

What is the common name of the molecule shown?

A)acetic acid
B)butyric acid
C)formic acid
D)lactic acid
E)oxalic acid

Question 29

What is the IUPAC name of the molecule shown?

A)diethanoic acid
B)ethanedioc
C)dibutanoic acid
D)butanedioic acid
E)pentanedioic acid

Question 30

Which molecule is acetic acid?

A)

B)

C)

D)

E)

Question 31

Which equation correctly represents the dissociation of a carboxylic acid in water?

A)CH₃COOH + H₂O

CH₃CHCOOH₂⁺ + OH^-
B)CH₃COOH

CH₃COO^- + H⁺
C)CH₃COOH + H₂O

CH₃COO^- + H₃O⁺
D)CH₃COOH + H₃O⁺

CH₃COOH₂⁺ + H₂O
E)CH₃COOH + 2 H₂O

CH₃COO^2- + 2 H₃O⁺

Question 32

What is the IUPAC name of the compound shown?
CH₃CH₂COOCH₃

A)2-butanoic acid
B)3-butanoic acid
C)methyl ethanoate
D)propyl methanoate
E)methyl propanoate

Question 33

The solubility of compounds containing the carboxylic acid group can be increased by reaction with

A)sulfuric acid.
B)nitric acid.
C)sodium hydroxide.
D)water.
E)benzoic acid.

Question 34

What is the common name of the molecule shown?

A)ethyl butanoate
B)butyl ethanoate
C)ethyl butyrate
D)butyl acetate
E)2-hexanoic ester

Question 35

When common names are used for acids,the underlined carbon atom in the molecule shown would be designated as the ________ C atom.

A)alpha
B)beta
C)gamma
D)#1
E)#2

Question 36

An alpha hydroxy carboxylic acid has an additional -OH group attached to the molecule at which location?

A)the carbonyl carbon atom
B)the #2 carbon atom
C)the carbon atom farthest from the carboxyl group
D)the carbon atom that contains the amine group
E)none of the above

Question 37

Which molecule is oxalic acid?

A)

B)

C)

D)

E)

Question 38

What is the IUPAC name of the compound shown?

A)2-methyl propanamide
B)N-methyl propanamide
C)2-methyl butanamide
D)3-methyl butanamide
E)N-methyl butanamide

Question 39

Which acid would be expected to have the highest boiling point?

A)acetic
B)benzoic
C)formic
D)oxalic
E)stearic

Question 40

The ion formed from a carboxylic acid is called the

A)carboxylate anion.
B)carboxylate cation.
C)ester anion.
D)ester cation.
E)amide cation.

Question 41

In the production of an ester,the carboxylic acid loses which atom or group of atoms?

A)oxygen from the C=O
B)H from the OH group
C)the OH group
D)the entire COOH group
E)oxygen from the OH

Question 42

The reactants needed to produce simple polyesters are

A)diacids and dialcohols.
B)diacids and diamines
C)diamines and dialcohols.
D)alkenes and catalysts.
E)diacids and phosphates.

Question 43

The products of basic hydrolysis of an ester are

A)another ester + water.
B)alcohol + acid.
C)alcohol + water.
D)acid + water.
E)carboxylate salt + alcohol.

Question 44

Hydrolysis of the ester ethyl acetate produces

A)ethanol and acetic acid.
B)butanol.
C)butanal and ethanol.
D)ethanal and acetic acid.
E)butanoic acid.

Question 45

The common chemical name of aspirin is

A)acetamide.
B)acetylsalicylic acid.
C)phenylalanyl aspartic acid.
D)acetaminophen.
E)lidocaine.

Question 46

Reaction of an ester with a strong base is called

A)reverse esterification.
B)esterification.
C)saponification.
D)oxidation.
E)condensation.

Question 47

When an alcohol reacts with a carboxylic acid the major product is

A)an amide.
B)an amine.
C)an ester.
D)a salt.
E)a soap.

Question 48

The functional groups in the aspirin molecule shown are

A)aromatic,carboxylic acid.
B)aromatic,ester.
C)carboxylic acid,ester.
D)aromatic,carboxylic acid,ester.
E)amide,aromatic,carboxylic acid.

Question 49

Which carboxylic acid is used to prepare the ester shown?

A)CH₃CH₂COOH
B)CH₃COOH
C)(CH₃)₂CHCOOH
D)(CH₃)₂CHCH₂COOH
E)CH₃ (C H₂


COOH

Question 50

The products of acid hydrolysis of an ester are

A)another ester + water.
B)alcohol + acid.
C)alcohol + water.
D)acid + water.
E)salt + water.

Question 51

What are the major organic products of the reaction shown?

A)CH₃CH₂CH₂COOH + HOCH₂CH₃
B)CH₃CH₂CH₂COO^- + ⁺H₂OCH₂CH₃
C)CH₃COOH + HOCH₂CH₂CH₂CH₃
D)CH₃CH₂CH₂CH₂OH + CH₃CH₂OH
E)CH₃CH₂CH₂COOH + CH₃COOH

Question 52

The reactants needed to produce simple polyamides (nylons)are

A)diacids and dialcohols.
B)diacids and diamines
C)diamines and dialcohols.
D)alkenes and catalysts.
E)diacids and phosphates.

Question 53

Reaction of a carboxylic acid with a base like sodium hydroxide,NaOH gives ________

A)a carboxylate salt.
B)an alkoxide salt.
C)an ester.
D)an alcohol.
E)none of the above.

Question 54

Reaction of butanoic acid with ethanol produces

A)butyl ethanoate.
B)ethyl butanoate.
C)butyl ethanamide.
D)ethyl butanamide.
E)butyl ethyl ester.

Question 55

The potassium or sodium salt of a long chain carboxylic acid is called a

A)soap.
B)triglyceride.
C)ester.
D)emollient.
E)none of the above

Question 56

What is the major organic product of the reaction shown?

A)

B)

C)

D)

E)
CH₃CH₂CH₂CH₂OCH₂OCH(CH₃)₂

Question 57

Which formula correctly illustrates the form which acetic acid would take in a basic solution?

A)

B)

C)

D)

E)

Question 58

Which of these compounds is the most soluble in water?

A)CH₃CH₂CH₂CH₂CH₂COOH
B)CH₃CH₂CH₂CH₂CH₂COO^-Na⁺
C)CH₃CH₂CH₂CH₂CH₂OH
D)CH₃CH₂CH₂CH₂CH₂CH₃
E)CH₃CH₂OCH₂CH₂CH₃

Question 59

Which of the following conditions would favor the carboxylate ion form of a carboxylic acid?

A)low pH
B)high pH
C)both A and B
D)neither A nor B

Question 60

When an amine reacts with a carboxylic acid at high temperature the major product is

A)an ester.
B)an amide.
C)a thiol.
D)an ether.
E)an alcohol.

Question 61

Phosphate esters are prepared from

A)phosphoric acid + alcohol.
B)phosphoric acid + ester.
C)phosphoric acid + carboxylic acid.
D)phosphate + ester.
E)phosphate + alcohol.

Question 62

This compound is

A)an anhydride only.
B)an ester only.
C)both an ester and an anhydride.
D)neither an ester nor an anhydride.
E)phosphoric acid.

Question 63

The amide produced from pentanoic acid and ammonia is

A)N-pentanamide.
B)N-methylpentanamide.
C)pentanoicamide.
D)pentanamide.

Question 64

The two monomers used to make Dacron polyester fabric are

A)ethylene glycol and mylar.
B)terephthalic acid and mylar.
C)propylene glycol and mylar.
D)ethylene glycol and terephthalic acid.
E)none of the above

Question 65

Hydrolysis of a carboxylic acid ester using base is called ________.

A)saponification
B)decarboxylation
C)detoxification
D)alcoholysis
E)extraction.

Question 66

Match the following.
ester

A)a molecule that contains one phosphate ester linkage and one phosphoric anhydride linkage
B)a molecule that contains one phosphate ester linkage and two phosphoric anhydride linkages
C)a polymer produced by reacting diamines with diacids or diacyl chlorides
D)a functional group formed when two acid molecules give up one water molecule
E)a functional group consisting of an amine group bonded to a carbonyl carbon
F)the type of ester produced when phosphoric acid reacts with two molecules of alcohol
G)a functional group consisting of a carbonyl carbon with a single bond to another oxygen; the remaining bonds are formed with R groups
H)the carbon atom bonded directly to the carbonyl carbon atom
I)the type of ester produced when phosphoric acid reacts with three molecules of alcohol
J)The common name of this compound is acetic acid.
K)the type of ester produced when phosphoric acid reacts with one molecule of alcohol
L)the transfer of a phosphoryl group from one molecule to another
M)The common name of this compound is formic acid.

Question 67

When an amide is hydrolyzed under basic conditions,the products are

A)an amine and a carboxylic acid.
B)an amine and a carboxylate ion.
C)an ammonium ion and a carboxylate ion.
D)an ammonium ion and a carboxylic acid.
E)There is no reaction.

Question 68

Match the following.
ethanoic acid

A)a molecule that contains one phosphate ester linkage and one phosphoric anhydride linkage
B)a molecule that contains one phosphate ester linkage and two phosphoric anhydride linkages
C)a polymer produced by reacting diamines with diacids or diacyl chlorides
D)a functional group formed when two acid molecules give up one water molecule
E)a functional group consisting of an amine group bonded to a carbonyl carbon
F)the type of ester produced when phosphoric acid reacts with two molecules of alcohol
G)a functional group consisting of a carbonyl carbon with a single bond to another oxygen; the remaining bonds are formed with R groups
H)the carbon atom bonded directly to the carbonyl carbon atom
I)the type of ester produced when phosphoric acid reacts with three molecules of alcohol
J)The common name of this compound is acetic acid.
K)the type of ester produced when phosphoric acid reacts with one molecule of alcohol
L)the transfer of a phosphoryl group from one molecule to another
M)The common name of this compound is formic acid.

Question 69

When an amide is hydrolyzed under acidic conditions,the products are

A)an amine and a carboxylic acid.
B)an amine and a carboxylate ion.
C)an ammonium ion and a carboxylate ion.
D)an ammonium ion and a carboxylic acid.
E)There is no reaction.

Question 70

Match the following.
acid anhydride

A)a molecule that contains one phosphate ester linkage and one phosphoric anhydride linkage
B)a molecule that contains one phosphate ester linkage and two phosphoric anhydride linkages
C)a polymer produced by reacting diamines with diacids or diacyl chlorides
D)a functional group formed when two acid molecules give up one water molecule
E)a functional group consisting of an amine group bonded to a carbonyl carbon
F)the type of ester produced when phosphoric acid reacts with two molecules of alcohol
G)a functional group consisting of a carbonyl carbon with a single bond to another oxygen; the remaining bonds are formed with R groups
H)the carbon atom bonded directly to the carbonyl carbon atom
I)the type of ester produced when phosphoric acid reacts with three molecules of alcohol
J)The common name of this compound is acetic acid.
K)the type of ester produced when phosphoric acid reacts with one molecule of alcohol
L)the transfer of a phosphoryl group from one molecule to another
M)The common name of this compound is formic acid.

Question 71

Match the following.
amide group

A)a molecule that contains one phosphate ester linkage and one phosphoric anhydride linkage
B)a molecule that contains one phosphate ester linkage and two phosphoric anhydride linkages
C)a polymer produced by reacting diamines with diacids or diacyl chlorides
D)a functional group formed when two acid molecules give up one water molecule
E)a functional group consisting of an amine group bonded to a carbonyl carbon
F)the type of ester produced when phosphoric acid reacts with two molecules of alcohol
G)a functional group consisting of a carbonyl carbon with a single bond to another oxygen; the remaining bonds are formed with R groups
H)the carbon atom bonded directly to the carbonyl carbon atom
I)the type of ester produced when phosphoric acid reacts with three molecules of alcohol
J)The common name of this compound is acetic acid.
K)the type of ester produced when phosphoric acid reacts with one molecule of alcohol
L)the transfer of a phosphoryl group from one molecule to another
M)The common name of this compound is formic acid.

Question 72

When an alcohol reacts with phosphoric acid,the product is referred to as a

A)phosphate salt.
B)phosphate ester.
C)phosphate anion.
D)pyrophosphate.
E)none of the above

Question 73

Which of the following might be obtained as one of the products in this reaction?

A)

B)

C)

D)

Question 74

Match the following.
alpha carbon

A)a molecule that contains one phosphate ester linkage and one phosphoric anhydride linkage
B)a molecule that contains one phosphate ester linkage and two phosphoric anhydride linkages
C)a polymer produced by reacting diamines with diacids or diacyl chlorides
D)a functional group formed when two acid molecules give up one water molecule
E)a functional group consisting of an amine group bonded to a carbonyl carbon
F)the type of ester produced when phosphoric acid reacts with two molecules of alcohol
G)a functional group consisting of a carbonyl carbon with a single bond to another oxygen; the remaining bonds are formed with R groups
H)the carbon atom bonded directly to the carbonyl carbon atom
I)the type of ester produced when phosphoric acid reacts with three molecules of alcohol
J)The common name of this compound is acetic acid.
K)the type of ester produced when phosphoric acid reacts with one molecule of alcohol
L)the transfer of a phosphoryl group from one molecule to another
M)The common name of this compound is formic acid.

Question 75

Match the following.
nylon

A)a molecule that contains one phosphate ester linkage and one phosphoric anhydride linkage
B)a molecule that contains one phosphate ester linkage and two phosphoric anhydride linkages
C)a polymer produced by reacting diamines with diacids or diacyl chlorides
D)a functional group formed when two acid molecules give up one water molecule
E)a functional group consisting of an amine group bonded to a carbonyl carbon
F)the type of ester produced when phosphoric acid reacts with two molecules of alcohol
G)a functional group consisting of a carbonyl carbon with a single bond to another oxygen; the remaining bonds are formed with R groups
H)the carbon atom bonded directly to the carbonyl carbon atom
I)the type of ester produced when phosphoric acid reacts with three molecules of alcohol
J)The common name of this compound is acetic acid.
K)the type of ester produced when phosphoric acid reacts with one molecule of alcohol
L)the transfer of a phosphoryl group from one molecule to another
M)The common name of this compound is formic acid.

Question 76

What are the products of this reaction?

A)

B)

C)

D)

Question 77

Match the following.
phosphate triester

A)a molecule that contains one phosphate ester linkage and one phosphoric anhydride linkage
B)a molecule that contains one phosphate ester linkage and two phosphoric anhydride linkages
C)a polymer produced by reacting diamines with diacids or diacyl chlorides
D)a functional group formed when two acid molecules give up one water molecule
E)a functional group consisting of an amine group bonded to a carbonyl carbon
F)the type of ester produced when phosphoric acid reacts with two molecules of alcohol
G)a functional group consisting of a carbonyl carbon with a single bond to another oxygen; the remaining bonds are formed with R groups
H)the carbon atom bonded directly to the carbonyl carbon atom
I)the type of ester produced when phosphoric acid reacts with three molecules of alcohol
J)The common name of this compound is acetic acid.
K)the type of ester produced when phosphoric acid reacts with one molecule of alcohol
L)the transfer of a phosphoryl group from one molecule to another
M)The common name of this compound is formic acid.

Question 78

One requirement for the reactants in the formation of polyester is that each molecule contain

A)at least one carbon-carbon double bond.
B)one aromatic ring.
C)at least two functional groups that can form ester linkages.
D)an amine group somewhere on the carbon skeleton.
E)none of these

Question 79

Match the following.
methanoic acid

A)a molecule that contains one phosphate ester linkage and one phosphoric anhydride linkage
B)a molecule that contains one phosphate ester linkage and two phosphoric anhydride linkages
C)a polymer produced by reacting diamines with diacids or diacyl chlorides
D)a functional group formed when two acid molecules give up one water molecule
E)a functional group consisting of an amine group bonded to a carbonyl carbon
F)the type of ester produced when phosphoric acid reacts with two molecules of alcohol
G)a functional group consisting of a carbonyl carbon with a single bond to another oxygen; the remaining bonds are formed with R groups
H)the carbon atom bonded directly to the carbonyl carbon atom
I)the type of ester produced when phosphoric acid reacts with three molecules of alcohol
J)The common name of this compound is acetic acid.
K)the type of ester produced when phosphoric acid reacts with one molecule of alcohol
L)the transfer of a phosphoryl group from one molecule to another
M)The common name of this compound is formic acid.

Question 80

Nylons and proteins are both referred to as polyamides because

A)each reactant molecule contains an amide group.
B)they are produced by reaction between an amide and an ester.
C)they are formed when an acid reacts with ammonia.
D)they are produced by basic hydrolysis of an amine.
E)they are formed when an acid functional group reacts with an amine functional group.