Deck 16: Carboxylic Acids, Esters, and Other Acid Derivatives

Question 1

The IUPAC name for the compound is

A) 2-methyl-4-butanoic acid
B) 2-methyl-4-pentanoic acid
C) 3-methylbutanoic acid
D) 3-methylpentanoic acid

Answer 1

3-methylbutanoic acid

Question 2

Which of the following statements concerning acid anhydrides is incorrect?

A) They undergo hydrolysis to produce the parent carboxylic acid.
B) They are generally less reactive than the corresponding acid chloride.
C) They have structures in which three oxygen atoms are present.
D) They are produced by reacting two carboxylic acids with each other.

Answer 2

They are produced by reacting two carboxylic acids with each other.

Question 3

In which of the following pairs of types of compounds is the first member of the pair classified as an acyl compound and the second member of the pair classified as a carbonyl compound.

A) carboxylic acid, ester
B) ester, acid chloride
C) aldehyde, ketone
D) ketone, carboxylic acid

Answer 3

ketone, carboxylic acid

Question 4

The functional group present in carboxylic acids is called a

A) carbonyl group
B) carboxyl group
C) carboxylate group
D) carbohydroxyl group

Question 5

Which of the following statements concerning the acid strength of carboxylic acids is correct?

A) All are weak acids.
B) All are strong acids.
C) Aromatic acids are strong and nonaromatic acids are weak.
D) Unbranched acids are weak and branched acids are strong.

Question 6

Which of the following is a general structural representation for an ester?

A)
B)
C)
D)

Question 7

Esters are produced through the reaction of

A) a ketone and an ether
B) an alcohol and a carboxylic acid
C) a carboxylic acid and an aldehyde
D) a ketone and an alcohol

Question 8

Carboxylic acids may be prepared by oxidation of

A) ketones
B) secondary alcohols
C) primary alcohols
D) tertiary alcohols

Question 9

Which of the following acids would produce a carboxylate ion with a minus-two charge?

A)
B)
C)
D)

Question 10

Carboxylic acid salts may be converted to their "parent" carboxylic acids by reacting them with

A) a weak base such as ammonia
B) a strong acid such as HBr
C) an alcohol such as ethanol
D) a phenol

Question 11

Which of the following statements concerning the properties of carboxylic acids is incorrect?

A) Short-chain monocarboxylic acids are liquids at room temperature.
B) Carboxylic acids have higher boiling points than alcohols of similar molecular mass.
C) Carboxylic acids cannot hydrogen bond to water.
D) Carboxylic acids can hydrogen bond to each other.

Question 12

The monomers for the formation of a polyester are

A) a dicarboxylic acid and a monoalcohol.
B) a dicarboxylic acid and a dialcohol.
C) two diesters.
D) two monoesters.

Question 13

The IUPAC name for the ester is

A) butyl methanoate
B) methyl butanoate
C) methyl butyl ester
D) methyl carboxybutane

Question 14

Which of the following statements concerning carboxylate ions is correct?

A) They may be negatively or positively charged.
B) Carboxylate ions formed from dicarboxylic acids carry a -2 charge.
C) They contain more carbon atoms than their parent acids.
D) They are mostly positively charged.

Question 15

The common name for the C₆ unbranched dicarboxylic acid is

A) pimelic acid
B) adipic acid
C) oxalic acid
D) succinic acid

Question 16

Which of the following polyfunctional carboxylic acids is incorrectly characterized?

A) tartaric acid, C₄ dihydroxydiacid
B) malic acid, C₄ hydroxydiacid
C) pyruvic acid, C₃ ketoacid
D) acrylic acid, C₃ ketodiacid

Question 17

Which of the following is the general formula for a phosphate monoester?

A)
B)
C)
D)

Question 18

When an ester undergoes saponification, one reaction product is

A) water
B) a carboxylic acid
C) a ketone
D) a carboxylic acid salt

Question 19

The common names for the C₂ mono- and dicarboxylic acids are, respectively,

A) formic acid and acetic acid
B) acetic acid and formic acid
C) oxalic acid and acetic acid
D) acetic acid and oxalic acid

Question 20

The ester obtained by reacting methanol and ethanoic acid is called

A) methyl ethane
B) methyl ethanoate
C) ethyl methanoate
D) ethane methanoate

Question 21

Which of the following statements concerning the boiling points of carboxylic acids is correct?

A) They are higher than those of corresponding alcohols.
B) They are lower than those of corresponding alkanes.
C) They are lower than those of corresponding aldehydes.
D) More than one correct response.
E) No correct response.

Question 22

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) A carboxylic acid and its corresponding carboxylate ion differ in the number of oxygen atoms they contain.
(2) In ester hydrolysis, the carbon-oxygen double bond breaks, producing an alcohol and a carboxylic acid.
(3) The acronym PET stands for polyester(terephthalate).

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 23

In which of the following pairs of carboxylic acids are both members of the pair dicarboxylic acids?

A) malonic acid and succinic acid
B) glutaric acid and butyric acid
C) oxalic acid and acetic acid
D) more than one correct response
E) no correct response

Question 24

Which of the following esters is paired with an incorrect IUPAC name for it?

A)
B)
C)
D) more than one correct response
E) no correct response

Question 25

Which of the following types of inorganic esters would contain two oxygen-carbon single bonds?

A) diphosphate monoester
B) phosphate triester
C) diphosphate diester
D) more than one correct response
E) no correct response

Question 26

Which of the following compounds is a constitutional isomer of ethyl ethanoate?

A) methyl methanoate
B) ethyl propanoate
C) butanoic acid
D) more than one correct response
E) no correct response

Question 27

In which of the following pairs of compounds does the first listed compound have a greater solubility in water than the second listed compound?

A) hexanoic acid, methanoic acid
B) sodium butanoate, butanoic acid
C) pentanoic acid, potassium pentanoate
D) more than one correct response
E) no correct response

Question 28

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) Hydrogen bonding is not possible between carboxylic acid molecules.
(2) The alpha-carbon atom in a carboxylic acid is the carbon atom to which the carboxyl group is attached.
(3) Sodium butanoate and ethyl butanoate are both examples of esters.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 29

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) The boiling points of esters are much higher than those of corresponding carboxylic acids.
(2) The compound benzoic acid is a heterocylic compound.
(3) In linear form, the ester functional group can be represented as -COOR.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 30

Which of the following carboxylic acids possesses two acidic hydrogen atoms?

A) butanedioic acid
B) 2-methylbutanoic acid
C) succinic acid
D) more than one correct response
E) no correct response

Question 31

The general structural difference between a carboxylic acid and an ester is the same as that between an

A) alcohol and an ether
B) aldehyde and a ketone
C) alkane and an alkene
D) more than one correct response
E) no correct response

Question 32

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) The compound 4-oxobutanoic acid contains both a carboxyl group and a carbonyl group.
(2) Aldehyde oxidation is a method for preparing a carboxylic acid.
(3) Both IUPAC and common names for esters consist of two words.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 33

Which of the following carboxylic acids is paired with its correct IUPAC name?

A)
B)
C)
D) more than one correct response
E) no correct response

Question 34

Which of the following pairings of ester common and IUPAC names is correct?

A) ethyl propionate and propyl ethanoate
B) propyl acetate and propyl ethanoate
C) ethyl butyrate and butyl ethanoate
D) more than one correct response
E) no correct response

Question 35

For which of the following types of carboxylic acid derivatives is the parent carboxylic acid(s) a product of the derivative's hydrolysis?

A) acid anhydride
B) acid chloride
C) ester
D) more than one correct response
E) no correct response

Question 36

Which of the following compounds could not be oxidized to a carboxylic acid?

A) propanal
B) 2-methyl-1-propanol
C) 2-methyl-2-propanol
D) more than one correct response
E) no correct response

Question 37

Which of the following is a correct notation for the carboxylic acid functional group?

A)
B)
C)
D) more than one correct response
E) no correct response

Question 38

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) The compound ethanoic acid contains two carbon atoms and two oxygen atoms.
(2) Unsubstituted short-chain monocarboxylic acids are completely miscible with water.
(3) The two reactants in an esterification reaction are a carboxylic acid and an aldehyde.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 39

For which of the following biochemically important polyfunctional carboxylic acids is its accompanying characterization correct?

A) fumaric acid; a keto acid
B) pyruvic acid; an unsaturated acid
C) lactic acid; a dihydroxy acid
D) more than one correct response
E) no correct response

Question 40

Which of the following functional groups is always found at the end of a carbon chain?

A) aldehyde
B) carboxylic acid
C) ketone
D) more than one correct response
E) no correct response

Question 41

Use the following to answer the questions below:
For each of the compound characterizations, select from the response list the number of constitutional isomers that exist. Responses may be used more than once or need not be used at all.
Chlorobenzoic acid

A)two
B)three
C)four
D)five

Question 42

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) Nitroglycerin is an example of a phosphate triester.
(2) In the body, aspirin is converted to salicylic acid, which is the "active" ingredient.
(3) Both ibuprofen and aspirin are propanoic acid derivatives.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 43

Use the following to answer the questions below:
For each pair of compounds, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Methyl propanoate, Propyl methanoate

A) have the same molecular formula but are different compounds
B) both contain a carbon ring system
C) contain the same number of carbon atoms but have different molecular formulas
D) two names for the same compound

Question 44

Use the following to answer the questions below:
Identify the missing reactant in each of the reactions using the response list. Responses may be used more than once or need not be used at all.


-Acid + ? $\rightarrow$ carboxylate ion + H₃O⁺

A) water
B) base in water
C) alcohol
D) carboxylic acid

Question 45

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) Hydrolysis of a mixed acid anhydride produces two different carboxylic acids as products.
(2) Short-chain unsubstituted monocarboxylic acids are strong acids, while their longer-chain counterparts are weak acids.
(3) The parent alcohol for the ester methyl acetate is methyl alcohol.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 46

Use the following to answer the questions below:
For each pair of compounds, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Butanedioic acid, Butanoic acid

A) have the same molecular formula but are different compounds
B) both contain a carbon ring system
C) contain the same number of carbon atoms but are not constitutional isomers
D) two names for the same compound

Question 47

Use the following to answer the questions below:
For each pair of carboxylic acids, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Acrylic acid, Pyruvic acid

A) Both are dicarboxylic acids.
B) Both are C₃ acids.
C) Both are monohydroxy acids.
D) Both are unsubstituted monocarboxylic acids.

Question 48

Use the following to answer the questions below:
For each of the compound characterizations, select from the response list the number of constitutional isomers that exist. Responses may be used more than once or need not be used at all.
Molecular formula of C₃H₆O₂

A)two
B)three
C)four
D)five

Question 49

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) Structurally, the difference between malonic acid and succinic acid is a -CH₂- grouping.
(2) A carboxylic acid salt is generally more soluble in water than the carboxylic acid from which it is obtained.
(3) Ester hydrolysis and ester saponification are "reverse" reactions of each other.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 50

Use the following to answer the questions below:
For each of the compound characterizations, select from the response list the number of constitutional isomers that exist. Responses may be used more than once or need not be used at all.
Saturated four-carbon dicarboxylic acid

A)two
B)three
C)four
D)five

Question 51

Use the following to answer the questions below:
For each of the compound characterizations, select from the response list the number of constitutional isomers that exist. Responses may be used more than once or need not be used at all.
Saturated four-carbon monocarboxylic acid

A)two
B)three
C)four
D)five

Question 52

Use the following to answer the questions below:
For each pair of carboxylic acids, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Citric acid, Lactic acid

A) Both are dicarboxylic acids.
B) Both are C₃ acids.
C) Both are monohydroxy acids.
D) Both are unsubstituted monocarboxylic acids.

Question 53

Use the following to answer the questions below:
For each pair of carboxylic acids, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Oxalic acid, Glutaric acid

A) Both are dicarboxylic acids.
B) Both are C₃ acids.
C) Both are monohydroxy acids.
D) Both are unsubstituted monocarboxylic acids.

Question 54

Use the following to answer the questions below:
For each pair of carboxylic acids, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Valeric acid, Caproic acid

A) Both are dicarboxylic acids.
B) Both are C₃ acids.
C) Both are monohydroxy acids.
D) Both are unsubstituted monocarboxylic acids.

Question 55

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) Pyruvic acid is the keto acid.
(2) Reaction of a carboxylic acid with a thiol produces a thioester, a compound containing two carbon-sulfur single bonds.
(3) One of the products of an esterification reaction is water.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 56

Use the following to answer the questions below:
For each pair of compounds, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Acetic acid, Ethanoic acid

A) have the same molecular formula but are different compounds
B) both contain a carbon ring system
C) contain the same number of carbon atoms but are not constitutional isomers
D) two names for the same compound

Question 57

Use the following to answer the questions below:
For each of the compound characterizations, select from the response list the number of constitutional isomers that exist. Responses may be used more than once or need not be used at all.
Saturated four-carbon ester

A)two
B)three
C)four
D)five

Question 58

Use the following to answer the questions below:
For each pair of carboxylic acids, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Fumaric acid, Succinic acid

A) Both are dicarboxylic acids.
B) Both are C₃ acids.
C) Both are monohydroxy acids.
D) Both are unsubstituted monocarboxylic acids.

Question 59

Use the following to answer the questions below:
For each pair of compounds, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.

Benzoic acid, Propyl butanoate

A) have the same molecular formula but are different compounds
B) both contain a carbon ring system
C) contain the same number of carbon atoms but are not constitutional isomers
D) two names for the same compound

Question 60

Use the following to answer the questions below:
In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices:
Statements: (1) "Pleasant odor" is a general characteristic of esters.
(2) Citric acid is both a tricarboxylic acid and a ketoacid.
(3) Esters and carboxylic acids with the same number of carbon atoms and the same degree of saturation are constitutional isomers.

A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.

Question 61

Use the following to answer the questions below:
Identify the missing reactant in each of the reactions using the response list. Responses may be used more than once or need not be used at all.


-Acid + ? $\rightarrow$ acid salt + H₂O

A) water
B) base in water
C) alcohol
D) carboxylic acid

Question 62

Use the following to answer the questions below:
Identify the missing reactant in each of the reactions using the response list. Responses may be used more than once or need not be used at all.


-Ester + ? $\rightarrow$ acid salt + alcohol

A) water
B) base in water
C) alcohol
D) carboxylic acid

Question 63

Use the following to answer the questions below:
Identify the missing reactant in each of the reactions using the response list. Responses may be used more than once or need not be used at all.


-Acid + ? $\rightarrow$ ester + H₂O

A) water
B) base in water
C) alcohol
D) carboxylic acid

Question 64

Use the following to answer the questions below:
Identify the missing reactant in each of the reactions using the response list. Responses may be used more than once or need not be used at all.


-Ester + ? $\rightarrow$ acid + alcohol

A) water
B) base in water
C) alcohol
D) carboxylic acid