Brown Organic Chemistry 6e Test Bank 1

CHAPTER 17—CARBOXYLIC ACIDS

MULTIPLE CHOICE

1. 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

ANS: A

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

ANS: B

3. 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

ANS: D

Brown Organic Chemistry 6e Test Bank 2

4. 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

ANS: A

5. 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

ANS: B

6. 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

ANS: A

Brown Organic Chemistry 6e Test Bank 3

7. 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

ANS: A

8. 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

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

Brown Organic Chemistry 6e Test Bank 4

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

Brown Organic Chemistry 6e Test Bank 5

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

a. 1 b. 2 c. 3 d. 4

ANS: B

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

a. 1 b. 2 c. 3 d. 4

ANS: C

Brown Organic Chemistry 6e Test Bank 6

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

a. 1 b. 2 c. 3 d. 4

ANS: B

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

a. 1 b. 2 c. 3 d. 4

ANS: C

Brown Organic Chemistry 6e Test Bank 7

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

a. 1 b. 2 c. 3 d. 4

ANS: A

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

a. 1 b. 2 c. 3 d. 4

ANS: A

Brown Organic Chemistry 6e Test Bank 8

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

a. 1 b. 2 c. 3 d. 4

ANS: B

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

a. 1 b. 2 c. 3 d. 4

ANS: B

Brown Organic Chemistry 6e Test Bank 9

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

a. 1 b. 2 c. 3 d. 4

ANS: C

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

a. 1 b. 2 c. 3 d. 4

ANS: A

Brown Organic Chemistry 6e Test Bank 10

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

a. 1 b. 2 c. 3 d. 4

ANS: C

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

a. 1 b. 2 c. 3 d. 4

ANS: A

Brown Organic Chemistry 6e Test Bank 11

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

a. 1 b. 2 c. 3 d. 4

ANS: D

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

a. 1 b. 2 c. 3 d. 4

ANS: D

Brown Organic Chemistry 6e Test Bank 12

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

a. 1 b. 2 c. 3 d. 4

ANS: C

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

a. 1 b. 2 c. 3 d. 4

ANS: C

Brown Organic Chemistry 6e Test Bank 13

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

a. CH3OH, H2SO4

b. CH3I, H2SO4

c. NaOCH3

d. CH3Li

ANS: A

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

a. CH3I, H2SO4

b. CH3MgBr

c. LiOCH3

d. CH2N2

ANS: D

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

a. 1. LiAlH4; 2. H3O+

b. H2, Pt

c. 1. NaBH4; 2. H2O

d. NaH

ANS: A

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

a. 1. LiAlH4; 2. H3O+

b. H2, Pt

c. 1. NaBH4; 2. H2O

d. NaH

ANS: B

Brown Organic Chemistry 6e Test Bank 14

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

a. 1. LiAlH4; 2. H3O+

b. H2, Pt

c. 1. NaBH4; 2. H2O

d. NaH

ANS: C

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

a. NaCl

b. HCl

c. SOCl2

d. 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

Brown Organic Chemistry 6e Test Bank 15

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:

Brown Organic Chemistry 6e Test Bank 16

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?

Brown Organic Chemistry 6e Test Bank 17

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:

Brown Organic Chemistry 6e Test Bank 18

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: