Douglas County High School, Minden

ORGO CHEM 1020

Chapter 10 -- Carboxylic Acids and Their Derivatives

MULTIPLE CHOICE

1)What is the common name for CH₃COOH?

1. 1. formic acid
   2. acetic acid
   3. propionic acid
   4. oxalic acid
   5. malonic acid

2. Which of the following represents p-bromobenzoic acid?
   1. D)

1. 2. E)

C)

3. The IUPAC name for succinic acid is butanedioic acid. What is the structure of succinic acid?
   1. CH₃CH₂CH₂CO₂H
   2. CH₃CH=CHCO₂H
   3. HO₂CCH₂CH₂CO₂H
   4. CH₃CH₂CH₂CO₃H
   5. HOCH₂CH₂CH₂CO₂H

4. What is a correct name for the following structure?

1. 1. pentanoic acid
   2. cyclopentanecarboxylic acid
   3. cyclopentanoic acid
   4. cyclopentylacetic acid
   5. formyl cyclopentane

5. Which of the following carboxylic acids is terephthalic acid?

1. 1. I
   2. II
   3. III
   4. IV
   5. V

6. What is the IUPAC name of the following molecule?

1. 1. cyclohexyl propanoate
   2. cyclohexyl acetate
   3. ethyl cyclohexanoate
   4. propyl cyclohexanoate
   5. propanoyl cyclohexyl ether

7. What is the name of the following molecule, (CH₃)₂CHCONH₂?
   1. 2-methylpropanamide
   2. 3-methylpropanamide
   3. butyramide
   4. ?-methylbutyramide
   5. methylethanamide

8. What is the IUPAC name of CH₃CO₂CH(CH₃)₂?
   1. ethyl acetate

1. 2. propyl acetate
   3. isopropyl ethanoate
   4. ethyl propanoate
   5. dimethyl acetate

9. Which of the following molecules is not an anhydride?
   1. D)

1. 2. 
      E)

C)

10. The IUPAC name for                                               is
    1. potassium 3-bromopropanoate.
    2. potassium 2-bromopropanoate.
    3. potassium 3-bromopropionate.
    4. potassium ?-bromopropionate.
    5. potassium ?-bromopropanoate.

11. The IUPAC name for                                                               is
    1. 2-bromoisopropyl isopropanoate.
    2. isopropyl-2-bromoisobutanoate.
    3. isopropyl-2-bromo-2-methylpropanoate.
    4. 2-bromoisobutanoyl-2-propanoate.
    5. isopropyl-2-bromo-3-methylbutanoate.

12. The formula for butanoic anhydride is

A)

B)

C)

D)

E)

13. Which of the following molecules would have the highest boiling point?
    1. CH₃CO₂H
    2. CH₃CH₂OH
    3. CH₃CHO
    4. CH₃CH=CH₂
    5. HCO₂H

14. Which of the following statements regarding                                          is false?
    1. Rotation around the C—N bond is restricted.
    2. The carbonyl group, NH group, and both methyl carbons lie in a plane.
    3. The nitrogen is strongly basic.
    4. The C—N bond is shorter than the C—N bond in amines.
    5. The compound is named Nmethylacetamide.

15. The boiling point of propanoic acid is higher than that of 1-butanol because:
    1. propanoic acid has a higher molecular weight than 1-butanol.
    2. propanoic acid is more soluble in water than 1-butanol.
    3. propanoic acid is a better hydrogen bond donor than 1-butanol.
    4. propanoic acid forms hydrogen bonded dimers and 1-butanol does not.
    5. 1-butanol forms hydrogen bonded dimers and propanoic acid does not.

16. Which of the following compounds undergoes hydrolysis at the fastest rate upon reaction with sodium hydroxide in water?

1. 1. I
   2. II
   3. III
   4. IV
   5. V

17. Which structure best describes the double bond character of the amide bond in acetamide?

1. 1. I
   2. II
   3. III
   4. IV
   5. V

18. Which of the following molecules is the weakest acid?
    1. CH₃CH₂CO₂H
    2. CH₃CH₂CH₃
    3. CH₃CH₂OH
    4. CH₃CH₂NH₂
    5. H₂O

19. Which of the following molecules has the most acidic ?-hydrogen?

A)

B)

C)

D)

E)

20. The expected order of decreasing acidity for the following is:

A) 2 > 3 > 4 > 1

B) 2 > 1 > 4 > 3

C) 1 > 2 > 3 > 4

D) 3 > 2 > 1 > 4

E)   1 > 3 > 4 > 2

F)   3 > 4 > 1 > 2

21. Rank the following according to their relative acidities

A) 3>2>1

B) 1>2>3

C) 2>3>1

D) 3>1>2

E)   2>1>3

22. Saponification of                                                                      is expected to give:

A)

B)

C)

D)

E)

23. The mechanism of saponification is
    1. nucleophilic aromatic substitution.
    2. nucleophilic acyl substitution.
    3. electrophilic aromatic substitution.
    4. S_N2.
    5. S_N1.

24. The following structure is an intermediate in the reaction of

1. 1. CH₃CO₂CH₃ with HCl.
   2. CH₃COCl with CH₃O^– Na⁺.
   3. CH₃CO₂CH₃ with HOCl.
   4. CH₃CH(OCH₃)₂ with Cl₂.
   5. CH₃Cl with (CH₃)₂C=O.

25. 
    Which structure represents the tetrahedral intermediate in the following reaction?

1. 1. D)

1. 2. E)

C)

26. 
    What is the product of the following reaction sequence?

A)

B)

C)

D)

E)

27. 
    The product of the following reaction sequence is:

1. 1. D)

1. 2. E)

C)

28. Acid chlorides react with alcohols to give:
    1. ketones
    2. esters
    3. acetals
    4. amides
    5. carboxylic acids

29. Which of the following carbonyl compounds reacts fastest with water?
    1. carboxylic acid
    2. ester
    3. ketone
    4. acid chloride
    5. amide

30. Oxidation of                                                                   with KMnO₄

A)

C)

D)

E)

31. (CH₃)₃CCO₂H can best be prepared by:

A)

B)

C)

D)

E)

32. The product(s) from                                                                                                         are:

A)

B)

C)

D)

E)

33. Treatment of 1 mole of CH₃CH₂CO₂CH₂CH₃ with 2 moles of Na^{+ —}OCH₂CH₃ followed by the addition of an aqueous solution of acid gives

B)

D)

E) no reaction

34. Benzoic acid cannot be prepared by which one of the following methods?

A)

B)

C)

D)

E)

35. The expected product of the reaction                                                                                                  is:

A)

B)

C)

D)

E)