CHAPTER 17CARBOXYLIC ACIDS

MULTIPLE CHOICE
1. What is the IUPAC name of the following compound

a.
b.
c.
d.

3,3-dimethylhexanoic acid
2,2-dimethylpentanoic acid
2,2-dimethylpentanal
4,4-dimethyl-6-hexanoyl acid

ANS: A
2. What is the IUPAC name of the following compound?

a.
b.
c.
d.

5,5-dimethyl-5-phenylpentanoic acid
5-methyl-5-phenylhexanoic acid
2,2-dimethylphenylpropanoic acid
5,5-dimethyl-5-phenylbutanal

ANS: B
3. What is the IUPAC name of the following compound?

a.
b.
c.
d.

(E)-4-ethyl-3-pentenoic acid
(Z)-4-ethyl-3-pentenoic acid
(E)-4-methyl-3-hexenoic acid
(Z)-4-methyl-3-hexenoic acid

ANS: D

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4. What is the IUPAC name of the following compound?

a.
b.
c.
d.

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

ANS: A
5. What is the IUPAC name of the following compound?

a.
b.
c.
d.

(2R,3R)-dihydroxybutanedioic acid
(2S,3S)-dihydroxybutanedioic acid
(2R,3S)-dihydroxybutanedioic acid
(2S,3R)-dihydroxybutanedioic acid

ANS: B
6. What is the IUPAC name of the following compound?

a.
b.
c.
d.

cis-4-methylcyclohexanecarboxylic acid
trans-4-methylcyclohexanecarboxylic acid
cis-3-methylcyclohexanecarboxylic acid
trans-3-methylcyclohexanecarboxylic acid

ANS: A

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

a.
b.
c.
d.

1 = salicylic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = phthalic acid

1 = terephthalic acid; 2 = salicylic acid; 3 = benzoic acid; 4 = phthalic acid
1 = salicylic acid; 2 = terephthalic acid; 3 = phthalic acid; 4 = benzoic acid
1 = phthalic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = salicylic acid

ANS: A
8. What is the correct assignment of the names of the following substituted benzenes?

a.
b.
c.
d.

1 = succinic acid; 2 = oxalic acid; 3 = malonic acid; 4 = adipic acid

1 = oxalic acid; 2 = malonic acid; 3 = succinic acid; 4 = adipic acid
1 = oxalic acid; 2 = succinic acid; 3 = adipic acid; 4 = malonic acid
1 = adipic acid; 2 = malonic acid; 3 = succinic acid; 4 = oxalic acid

ANS: B
9. Which of the following is the most soluble in water?
a. hexane
b. 1-pentanol
c. pentanal
d. butanoic acid
ANS: D
10. Which of the following is the most soluble in water?
a. acetic acid
b. pentanol
c. butanoic acid
d. pentanal
ANS: A

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11. Which of the following has the highest boiling point?

a. hexane
b. 1-pentanol
c. pentanal
d. butanoic acid
ANS: D
12. Which of the following has the highest boiling point?
a. acetic acid
b. pentanol
c. butanoic acid
d. pentanal
ANS: C
13. What is the approximate pKa value of acetic acid
a. 2
b. 5
c. 15
d. 35
ANS: B
14. 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.
ANS: C
15. 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
ANS: B
16. 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
ANS: B
17. 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
ANS: A

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

a.
b.
c.
d.

1
2
3
4

ANS: B
19. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C

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

a.
b.
c.
d.

1
2
3
4

ANS: B
21. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C

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

a.
b.
c.
d.

1
2
3
4

ANS: A
23. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A

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

a.
b.
c.
d.

1
2
3
4

ANS: B
25. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: B

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

a.
b.
c.
d.

1
2
3
4

ANS: C
27. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A

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

a.
b.
c.
d.

1
2
3
4

ANS: C
29. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A

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

a.
b.
c.
d.

1
2
3
4

ANS: D
31. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D

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

a.
b.
c.
d.

1
2
3
4

ANS: C
33. Which of the following carboxylic acids undergoes the most rapid thermal decarboxylation reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C

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

a.
b.
c.
d.

CH3OH, H2SO4
CH3I, H2SO4
NaOCH3
CH3Li

ANS: A
35. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

CH3I, H2SO4
CH3MgBr
LiOCH3
CH2N2

ANS: D
36. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

1. LiAlH4; 2. H3O+
H2, Pt
1. NaBH4; 2. H2O
NaH

ANS: A
37. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

1. LiAlH4; 2. H3O+
H2, Pt
1. NaBH4; 2. H2O
NaH

ANS: B

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

a.
b.
c.
d.

1. LiAlH4; 2. H3O+
H2, Pt
1. NaBH4; 2. H2O
NaH

ANS: C
39. What is the best choice of reagent to perform the following transformation?

a.
b.
c.
d.

NaCl
HCl
SOCl2
Cl2

ANS: C
40. 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
ANS: A
41. 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
ANS: A

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PROBLEM
1. What is the IUPAC name of the following compound?

ANS:
(Z)-2-butenoic acid
2. What is the IUPAC name of the following compound?

ANS:
(E)-3-pentenoic acid
3. What is the major organic product obtained from the following reaction?

ANS:

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

ANS:

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

ANS:

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

ANS:

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

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ANS:

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

ANS:

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

ANS:

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

ANS:

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

ANS:

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

ANS:

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