Deck 17: Carboxylic Acids

Question 1

What is the approximate pK_a value of acetic acid

A) −2
B) 5
C) 15
D) 35

Answer 1

5

Question 2

What is the IUPAC name of the following compound?

A) 5,5-dimethyl-5-phenylpentanoic acid
B) 5-methyl-5-phenylhexanoic acid
C) 2,2-dimethylphenylpropanoic acid
D) 5,5-dimethyl-5-phenylbutanal

Answer 2

5-methyl-5-phenylhexanoic acid

Question 3

Which of the following is the most soluble in water?

A) hexane
B) 1-pentanol
C) pentanal
D) butanoic acid

Answer 3

butanoic acid

Question 4

Which of the following statements is not true regarding benzoic acid acids?

A) The neutral acid is the predominant species in aqueous solution at pH <2.
B) The anionic carboxylate is the predominant species in aqueous solution at pH >7.
C) Sodium benzoate is less soluble in water than benzoic acid.
D) Benzoic acid is extracted out of diethyl ether by treatment with aqueous sodium bicarbonate.

Question 5

What is the IUPAC name of the following compound?

A) (E)-4-ethyl-3-pentenoic acid
B) (Z)-4-ethyl-3-pentenoic acid
C) (E)-4-methyl-3-hexenoic acid
D) (Z)-4-methyl-3-hexenoic acid

Question 6

What is the major organic product obtained from the following reaction?

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

Question 7

What is the IUPAC name of the following compound?

A) cis-4-methylcyclohexanecarboxylic acid
B) trans-4-methylcyclohexanecarboxylic acid
C) cis-3-methylcyclohexanecarboxylic acid
D) trans-3-methylcyclohexanecarboxylic acid

Question 8

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A) ICH₂COOH > ClCH₂COOH > FCH₂COOH
B) Cl₂CHCOOH > ClCH₂COOH > CH₃COOH
C) CH₃CH₂OH > FCH₂COOH > ClCH₂COOH
D) CH₃COOH > FCH₂COOH > CH₃CH₂OH

Question 9

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A) FCH₂COOH > CH₃COOH > F₂CHCOOH
B) FCH₂COOH > CH₃COOH > CH₃OH
C) CH₃CH₂OH > ClCH₂COOH > BrCH₂COOH
D) CH₃COOH > ClCH₂COOH > CH₃OH

Question 10

What is the correct assignment of the names of the following substituted benzenes?

A) 1 = succinic acid; 2 = oxalic acid; 3 = malonic acid; 4 = adipic acid
B) 1 = oxalic acid; 2 = malonic acid; 3 = succinic acid; 4 = adipic acid
C) 1 = oxalic acid; 2 = succinic acid; 3 = adipic acid; 4 = malonic acid
D) 1 = adipic acid; 2 = malonic acid; 3 = succinic acid; 4 = oxalic acid

Question 11

What is the major organic product obtained from the following reaction?

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

Question 12

What is the correct assignment of the names of the following substituted benzenes?

A) 1 = salicylic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = phthalic acid
B) 1 = terephthalic acid; 2 = salicylic acid; 3 = benzoic acid; 4 = phthalic acid
C) 1 = salicylic acid; 2 = terephthalic acid; 3 = phthalic acid; 4 = benzoic acid
D) 1 = phthalic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = salicylic acid

Question 13

Which of the following has the highest boiling point?

A) acetic acid
B) pentanol
C) butanoic acid
D) pentanal

Question 14

What is the IUPAC name of the following compound

A) 3,3-dimethylhexanoic acid
B) 2,2-dimethylpentanoic acid
C) 2,2-dimethylpentanal
D) 4,4-dimethyl-6-hexanoyl acid

Question 15

Which of the following is the most soluble in water?

A) acetic acid
B) pentanol
C) butanoic acid
D) pentanal

Question 16

Which of the following has the highest boiling point?

A) hexane
B) 1-pentanol
C) pentanal
D) butanoic acid

Question 17

What is the IUPAC name of the following compound?

A) 4-methyl-3-phenyl-3-pentenoic acid
B) 4,4-dimethyl-3-phenyl-3-butenoic acid
C) 3-phenyl-2-methyl-2-penten-5-oic acid
D) (Z)-3-methyl-2-phenyl-2-butenoic acid

Question 18

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A) FCH₂COOH > ClCH₂COOH > BrCH₂COOH
B) CH₃COOH > ClCH₂COOH > Cl₂CHCOOH
C) CH₃COOH > FCH₂COOH > CH₃CH₂OH
D) CH₃CH₂OH > FCH₂COOH > ClCH₂COOH

Question 19

What is the major organic product obtained from the following reaction?

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

Question 20

What is the IUPAC name of the following compound?

A) (2R,3R)-dihydroxybutanedioic acid
B) (2S,3S)-dihydroxybutanedioic acid
C) (2R,3S)-dihydroxybutanedioic acid
D) (2S,3R)-dihydroxybutanedioic acid

Question 21

Which of the following is a reactive intermediate in the thermal decarboxylation of a 1,3-diacid?

A) enol
B) carbocation
C) carbanion
D) carboxylate

Question 22

What is the major organic product obtained from the following reaction?

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

Question 23

What is the major organic product obtained from the following reaction?

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

Question 24

What is the major organic product obtained from the following reaction?

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

Question 25

What is the major organic product obtained from the following reaction?

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

Question 26

What is the best choice of reagent(s) to perform the following transformation?

A) CH₃OH, H₂SO₄
B) CH₃I, H₂SO₄
C) NaOCH₃
D) CH₃Li

Question 27

What is the best choice of reagent(s) to perform the following transformation?

A) CH₃I, H₂SO₄
B) CH₃MgBr
C) LiOCH₃
D) CH₂N₂

Question 28

Which of the following best describes the key mechanistic steps in the esterification of a carboxylic acid upon treatment with an alcohol in the presence of a strong acid?

A) addition followed by elimination
B) substitution followed by addition
C) elimination followed by addition
D) addition followed by decarboxylation

Question 29

What is the major organic product obtained from the following reaction?

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

Question 30

The structure of cis-1,3-cyclopentanedicarboxylic acid is shown below.

Question 31

What is the major organic product obtained from the following reaction?

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

Question 32

What is the major organic product obtained from the following reaction?

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

Question 33

What is the major organic product obtained from the following reaction?

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

Question 34

Which of the following carboxylic acids undergoes the most rapid thermal decarboxylation reaction?

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

Question 35

What is the major organic product obtained from the following reaction?

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

Question 36

What is the major organic product obtained from the following reaction?

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

Question 37

What is the major organic product obtained from the following reaction?

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

Question 38

What is the best choice of reagent to perform the following transformation?

A) NaCl
B) HCl
C) SOCl₂
D) Cl₂

Question 39

What is the major organic product obtained from the following reaction?

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

Question 40

Consider the data in the Table below to answer the following question:
Acidities of Substituted Benzoic and Acetic Acids
pK_as at 25°C
Y−C₆H₄COOH
Y
Y−CH₂COOH
meta
para
H
4.75
4.19
4.19
CN
2.47
3.64
3.55
OCH₃
3.57
4.09
4.46
The structure of the strongest acid in the table above is NC−CH₂−COOH.

Question 41

What is the major organic product obtained from the following reaction?

Question 42

What is the major organic product obtained from the following reaction?

Question 43

Malonic acid is an example of a β-ketoacid.

Question 44

The strongest acid of the following is indicated by the Roman numeral ______.

Question 45

What is the major organic product obtained from the following reaction?

Question 46

What is the major organic product obtained from the following reaction?

Question 47

When CO₂ is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, ____________ _____ is produced.

Question 48

Consider the data in the Table below to answer the following question:
Acidities of Substituted Benzoic and Acetic Acids
pK_as at 25°C
Y−C₆H₄COOH
Y
Y−CH₂COOH
meta
para
H
4.75
4.19
4.19
CN
2.47
3.64
3.55
OCH₃
3.57
4.09
4.46
The structure of the acid with the strongest conjugate base in the table above is CH₃COOH.

Question 49

What is the IUPAC name of the following compound?

Question 50

Consider the following reaction. $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H} \quad \underset{\Delta}{\stackrel{\mathrm{H}^{+}}{\longrightarrow}}$ The expected product is

Question 51

Pentanoic acid can be converted to its methyl ester in very high yield by reaction with ___________________.

Question 52

What is the IUPAC name of the following compound?

Question 53

Consider the following reaction. The major organic product obtained is

Question 54

Provide the correct name for the following compound which can be used to produce aspirin.

Question 55

The strongest acid of the following is indicated by the Roman numeral ______.

Question 56

Based on the following IR spectrum, this compound would be classified as aromatic carboxylic acid.
​ ​
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 11-07-08)

Question 57

Ethyl propanoate (CH₃CH₂COOCH₂CH₃) can be prepared by the reaction of ethanol with ____________ acid.

Question 58

Benzoic acid can be produced by the treatment of bromobenzene with 1. Mg, ether, and 2.) CO₂ followed by acidification.

Question 59

Consider the following ¹H NMR to answer the following question. Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 11-07-08)
This compound is known to contain both a −C=O group and an −OH group. Based on this spectrum, this compound would be classified as aliphatic carboxylic acid.

Question 60

Consider the following reaction. The major organic product obtained is

Question 61

What is the common name of the given compound? ​

A) Azelaic acid
B) Seabacic acid
C) Suberic acid
D) Adepic acid

Question 62

Which is the only carboxylic acid that does not have a hydrophobic hydrocarbon chain?

A) Adepic acid
B) Succinic acid
C) Formic acid
D) Acetic acid

Question 63

Select the compound that is most suitable to complete the given reaction. ? $\mathrm{CH}_{3} \mathrm{COOH}+? \rightarrow 3 \mathrm{CH}_{3} \mathrm{COCl}+\mathrm{H}_{3} \mathrm{PO}_{4}$

A) PCl₃
B) SOCl₂
C) HCl
D) PCl₅

Question 64

Match the structures with the most appropriate boiling points.
141.2^oC

A)CH3COOH
B)CH3(CH2)2COOH
C)CH3(CH2)4COOH
D)CH3CH2COOH

Question 65

Match the structures with the most appropriate boiling points.
118^oC

A)CH3COOH
B)CH3(CH2)2COOH
C)CH3(CH2)4COOH
D)CH3CH2COOH

Question 66

What is the major organic product obtained from the following sequence of reactions?

Question 67

What is the major organic product obtained from the following reaction?

Question 68

What is the IUPAC name of succinic acid?

A) butane-1,4-dioic acid
B) 1,1-butanedioic acid
C) propanedioic acid
D) propan-1,3-dioic acid

Question 69

Match the structures with the most appropriate boiling points.
163^oC

A)CH3COOH
B)CH3(CH2)2COOH
C)CH3(CH2)4COOH
D)CH3CH2COOH

Question 70

Identify the final product of the following reaction. ​

A)

B)

C)

D)

Question 71

What is the major organic product obtained from the following reaction?

Question 72

What is the major organic product obtained from the following reaction?

Question 73

What is the major organic product obtained from the following sequence of reactions?

Question 74

What is the major organic product obtained from the following reaction?

Question 75

Match the structures with the most appropriate boiling points.
205^oC

A)CH3COOH
B)CH3(CH2)2COOH
C)CH3(CH2)4COOH
D)CH3CH2COOH

Question 76

It is possible to reduce aldehydes and ketones selectively by using the less reactive _____ as the reducing agent.