Chapter 19: Carboxylic Acids and The Acidity of The O-H Bond

Chapter 1: Structure and Bonding
51. What is the product of the following reaction?
A) I B) II C) III D) IV
Chapter 19: Carboxylic Acids and the Acidity of the O-H Bond
1. What is the hybridization of the carbon atom in a carboxy group?

A) sp B) sp2 C) sp3 D) p
2. Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an
alcohol?
A) The carbon in the alcohol is sp2 hybridized and has a higher percent s-character that
lengthens the C-O bond in the alcohol.
B) The carbon in the carboxylic acid is sp3 hybridized and has a lower percent s-
character that shortens the C-O bond in the carboxylic acid.
C) The carbon in the carboxylic acid is sp hybridized and has a higher percent s-
D) The carbon in the carboxylic acid is sp2 hybridized and has a higher percent s-
3. What two groups make up the carboxylic acid group (RCOOH)?

A) Carbon dioxide and hydrogen C) Carbon monoxide and hydroxyl
B) Carbonyl and hydroxyl D) Carbonyl oxide and hydrogen
4. What is the correct IUPAC name of the following compound?
A) 4-Isopropyl-3-methylbutanoic acid C) 3,5-Dimethylhexanoic acid

B) 2,4-Dimethylhexanoic acid D) 3,5-Dimethy-1-hexanoic acid
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A) 3,5,5-Trimethylcyclohexanecarboxylic acid
B) 3,3,5-Trimethylcyclohexanecarboxylic acid
C) 3,3,5-Trimethylcyclohexanoic acid
D) 3,5,5-Trimethylcyclohexanoic acid
A) 2-sec-Butyl-4,4-dimethylnonanoic acid
B) 4,4-Dimethyl-2-isobutylnonanoic acid
C) 4,4-Dimethyl-2-sec-butylnonanoic acid
D) 2-Isobutyl-4,4-dimethylnonanoic acid
A) 3,4-Dimethylcyclohexanoic acid
B) 3,4-Dimethylcyclohexanecarboxylic acid
C) 4,5-Dimethylcyclohexanecarboxylic acid
D) 1,2-Dimethylcyclohexanecarboxylic acid
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8. What is the common name of the following compound?
A) -Methylbutyric acid C) -Methylvaleric acid

B) -Propylpropionic acid D) -Methylcaproic acid
A) ,-Dimethoxyvaleric acid C) 2,3-Dimethoxycaproic acid

B) 2,3-Dimethoxyvaleric acid D) ,-Dimethoxycaproic acid
A) ,-Dimethyl--fluorobutyric acid
B) -Fluoro-,-dimethylbutyric acid
C) -Fluoro-,,-trimethylpropionic acid
D) -Fluoro-,,-trimethylbutyric acid
A) Propanedioic acid C) Malonic acid

B) 1,3-propanedicarboxylic acid D) Succinic acid
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A) (E)-2-Hexenoic acid C) (E)-4-Hexenoic acid

B) (Z)-2-Hexenoic acid D) (Z)-4-Hexenoic acid
A) 2-Methoxypentanoic acid C) 4-Methoxybutanoic acid

B) 2-Methoxybutanoic acid D) 4-Methoxypentanoic acid
14. Which of the following is the structure of oxalic acid?
15. Which of the following is the correct IUPAC name for the following structure?
A) Potassium propanoate C) Potassium propanoic

B) Butanoic potassium D) Potassium butanoate
16. Which of the following is the most polar organic compound?

A) CH3CH2CH2CH3
B) CH3CH2CHO
C) CH3CH2CH2OH
D) CH3COOH
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17. Arrange the following compounds in order of increasing boiling point, putting the
compound with the lowest boiling point first.
A) I < II < III < IV C) III < II < IV < I

B) I < IV < II < III D) II < IV < I < III
18. Arrange the following compounds in order of decreasing water solubility, putting the
most soluble compound first.
A) I > II > III > IV C) I > II > IV > III

B) I > IV > II > III D) IV > III > II > I
19. Arrange the following compounds in order of increasing water solubility, putting the
least soluble compound first.
A) I < II < III < IV C) I < III < II < IV

B) II < I < III < IV D) IV < II < III < I
20. What two strong absorptions are characteristic of the IR spectrum of carboxylic acids?
A) A C=O absorption at 1710 cm-1 and a C-H absorption at 3000 cm-1.
B) A C=O absorption at 1710 cm-1 and an O-H absorption at 2500-3500 cm-1.
C) A C=O absorption at 1600 cm-1 and an O-H absorption at 2500-3000 cm-1.
D) A C-O absorption at 1500 cm-1 and an O-H absorption at 2500-3500 cm-1.
21. Where do the two noteworthy peaks of carboxylic acids appear in 1HNMR spectra?
A) Between 10 and 12 ppm for the OH proton and 2-2.5 ppm for the protons on the 
carbon to the carboxy group.
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B) Between 6 and 9 ppm for the OH proton and 2-2.5 ppm for the protons on the 
C) Between 10 and 12 ppm for the OH proton and 1-1.5 ppm for the protons on the 
D) Between 6 and 9 ppm for the OH proton and 1-1.5 ppm for the protons on the 
22. Why is pure acetic acid often called glacial acetic acid?
A) Because it freezes just below 0°C, forming white crystals.
B) Because it freezes just below 100°C, forming white crystals.
C) Because it freezes just below room temperature, forming white crystals.
D) Because it freezes just above room temperature, forming white crystals.
23. Which of the following reagents can accomplish the transformation below?
A) PCC, CH2Cl2 C) [1] O3; [2] H2O

B) [1] LiAlH4, THF; [2] H2O D) K2Cr2O7, H2SO4, H2O
24. What is the other product formed in the oxidation of the following terminal alkyne?
A) HCOOH B) HCOH C) CO2 D) CO
25. Which of the following cannot be the starting material for the following reaction?
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26. In the presence of strong acids, which of the oxygen atoms on the carboxyl group is
preferentially protonated and why?
A) Protonation occurs at the carbonyl oxygen because the resulting conjugate acid is
stabilized by resonance.
B) Protonation occurs at the carbonyl oxygen because the resulting conjugate base is
stabilized by the inductive effect.
C) Protonation occurs at the hydroxyl oxygen because the resulting conjugate acid is
stabilized by resonance.
D) Protonation occurs at the hydroxyl oxygen because the resulting conjugate base is
stabilized by the inductive effect.
27. Which of the following structures is the major contributor to the resonance hybrid of the
phenoxide anion?
28. Arrange the following compounds in order of increasing acidity, putting the least acidic
first.
A) I < II < III < IV C) III < IV < II < I

B) IV < III < II < I D) IV < II < III < I
29. Which of the following bases are strong enough to significantly deprotonate ethanol,
CH3CH2OH (pKa = 16)?
A) NaOCH3 B) NaOH C) NaH D) NaOCH2CH3
30. Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least
acidic.
A) Ha < Hb < Hc < Hd C) Hd < Ha < Hc < Hb

B) Hb < Hc < Ha < Hd D) Hb < Hc < Hd < Ha
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31. Rank the following compounds in order of decreasing acidity, putting the most acidic
first.
A) IV > III > I > II C) II > I > IV > III

B) IV > II > I > III D) II > I > III > IV
32. Rank the following compounds in order of increasing acidity, putting the least acidic
first.
A) II < III < I < IV C) IV < III < I < II

B) II < I < III < IV D) IV < I < II < III
first.
A) III < II < IV < I C) I < IV < II < III

B) III < IV < II < I D) I < II < III < IV
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first.
A) IV > III > II > I C) I > II > III > IV

B) IV > I > III > II D) IV > II > III > I
first.
A) I < II < III < IV C) IV < I < II < III

B) III < II < I < IV D) I < IV < III < II
first.
A) III > IV > I > II C) I > II > III > IV

B) IV > III > I > II D) IV > III > II > I
37. What physical property and reaction type are used by extraction as useful techniques to
separate and purify mixtures of compounds?
A) Physical property = solubility differences; reaction type = acid-base reaction.
B) Physical property = boiling point; reaction type = acid-base reaction.
C) Physical property = solubility differences; reaction type = oxidation-reduction.
D) Physical property = density; reaction type = oxidation-reduction.
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38. What would happen if a mixture of benzoic acid (C6H5COOH) and NaCl is added to a
separatory funnel containing H2O and CH2Cl2?
A) The benzoic acid would dissolve in the water layer and the NaCl would dissolve in
the organic layer.
B) The benzoic acid would dissolve in the organic layer and the NaCl would dissolve
in the water layer.
C) Both benzoic acid and NaCl would dissolve in the organic layer.
D) Both benzoic acid and NaCl would dissolve in the water layer.
39. What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH2Cl2
is treated with aqueous NaOH solution?
A) Benzoic acid would remain in the CH2Cl2 layer, and cyclohexanol would dissolve
in the aqueous layer.
B) Benzoic acid would dissolve in the aqueous layer while cyclohexanol would
remain in the CH2Cl2 layer.
C) The salt of benzoic acid would dissolve in the aqueous layer while cyclohexanol
would remain in the CH2Cl2 layer.
D) The salt of benzoic acid would remain in the CH2Cl2 layer while cyclohexanol
would dissolve in the aqueous layer.
compound first.
A) III < I < II < IV C) III < II < I < IV

B) IV < I < II < III D) II < IV < I < III
41. What is the overall charge of the amino acid, alanine, at pH = 2?

A) + 1 B) – 1 C) No overall charge D) + 2
A) + 1 B) – 1 C) No overall charge D) – 2

A) + 1 B) – 1 C) No overall charge D) + 2
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44. As applied to the chemistry of amino acids, what is the definition for the isoelectric
point?
A) The pH at which the amino acid exists primarily in its acidic form.
B) The pH at which the amino acid exists primarily in its basic form.
C) The pH at which the amino acid exists as a mixture of isomers.
D) The pH at which the amino acid exists primarily in its neutral form.
Chapter 20: Introduction to Carbonyl Chemistry;

Organometallic Reagents; Oxidation and Reduction
1. What is the name of the general reaction type that aldehydes and ketones undergo?
A) Electrophilic addition C) Nucleophilic substitution
B) Nucleophilic addition D) Electrophilic substitution
2. What is the name of the general reaction type that carboxylic acids, esters, and amides
undergo?
A) Electrophilic acyl addition C) Nucleophilic acyl substitution
B) Nucleophilic acyl addition D) Electrophilic acyl substitution
3. What are the two steps in a nucleophilic addition mechanism?

A) Nucleophilic attack followed by protonation.
B) Nucleophilic attack followed by deprotonation.
C) Nucleophilic attack followed by substitution.
D) Nucleophilic attack followed by elimination.
4. Which of the following terms explain why aldehydes are more reactive than ketones?
A) Electronegativity and resonance C) Electronegativity and hybridization
B) Hybridization and resonance D) Sterics and electronics
5. Why are ketones less reactive than aldehydes?

A) Ketones are more sterically hindered.
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Chapter 22: Carboxylic Acids and Derivatives
1. Which of the following is a lactam?
2. Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride?
A) Nitrogen is a better leaving group.
B) Chloride is a better leaving group.
C) Nitrogen donates more electron density into the carbonyl.
D) The amide anion is less basic.
3. What is the IUPAC name for the following compound?
A) methyl 3-methylbutanamide C) N-methyl 3-methylhexanamide
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B) 5-methylhexanamide D) N-methyl 3-methylbutanamide
A) 4-fluoro-3-methylbenzoate C) 3-methyl-4-fluorobenzoic acid

B) 4-fluoro-3-methylbenzoic acid D) 4-fluoro-5-methylbenzoic acid
5. What is the structure for acetic propanoic anhydride?
6. What is the structure for ethyl 4-chlorobenzoate?
7. What is the structure for 3-cyanocyclopentanone?
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A) 2-fluorobutanonitrile C) 3-fluoropentanonitrile
B) 2-fluoropentanonitrile D) 2-fluorobutylcyanide
9. Where is the carbonyl absorption found in the IR spectrum of a simple ester?

A) 2.5 ppm B) 2250 cm-1 C) 3800 cm-1 D) 1740 cm-1
10. Which of the following peaks would you see in the IR spectrum of a carboxylic acid?
A) A flat line (carboxylic acids are not IR active)
B) A sharp line at 2250 cm-1
C) A broad peak from 3800-2800 cm-1
D) A broad peak from 800-600 cm-1
11. You see an absorption at 2250 cm-1 in the IR spectrum of a compound. What kind of
functional group is present?
A) A ketone B) An aldehyde C) An ester D) A nitrile
12. Where do the carbonyl signals appear in the 13C NMR spectrum of carboxylic acid
derivatives?
A) 1700 cm-1 B) 180-160 ppm C) 2.5-3.0 ppm D) 100-80 ppm
13. Which structure is consistent with the following 1H NMR spectrum?
A) ethyl acetate C) 3,3-dimethyl-2-pentanone
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B) 2-propanone D) ethyl 2,2-dimethylpropionate
14. What is the first step in the general mechanism for nucleophilic acyl substitution?
A) Protonation of the carbonyl
B) Removal of an -proton
C) Addition of the nucleophile to the carbonyl
D) Loss of the leaving group
15. Why doesn't nucleophilic acyl substitution stop at the tetrahedral intermediate?
A) The nucleophile is too basic.
B) Reforming the carbonyl is energetically favorable.
C) The leaving group is unstable and wants to be negatively charged.
D) There is no tetrahedral intermediate.
16. Will the following reaction occur?
A) Yes B) No
A) Yes B) No
A) Yes B) No
19. Why is pyridine included in the reaction of an acid chloride and an amine or alcohol?
A) Pyridine will deprotonate the amine or alcohol, making it a better nucleophile.
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B) Pyridine will neutralize the acid by-product of the reaction.

C) Pyridine will protonate the carbonyl of the acid chloride, making it more reactive.
D) Pyridine will absorb the heat of the reaction.
22. How can you convert a carboxylic acid into an ester?

A) Heat with an alcohol and catalytic acid
B) Deprotonate with a base and react with an alcohol
C) Deprotonate with a base and react with an alkyl halide
D) Both (a) heat with an alcohol and catalytic acid and (c) deprotonate with a base and
react with an alkyl halide
E) Both (a) heat with an alcohol and catalytic acid and (b) deprotonate with a base and
react with an alcohol
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23. How can you convert a carboxylic acid into an acid chloride?
A) Heat with hydrochloric acid C) React with sodium chloride
B) React with thionyl chloride (SOCl2) D) React with Cl2 and FeCl3
25. What is the direct product of the base-promoted hydrolysis of an ester?

A) A nitrile B) A carboxylic acid C) An amide D) A carboxylic acid salt
26. Which of the following two amides will react more readily with a nucleophile? Why?
A) I, because it is less hindered C) I, because it is more strained

B) II, because it is less hindered D) II, because it is more strained
A) Hexanoic acid B) 1-Hexanamide C) Hexanal D) 1-Hexanamine
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28. What is the product of the following reaction (after acidic work-up)?
29. What reagent would you use for the following transformation?
A) LiAlH4 B) DIBAL-H C) NaBH4 D) H2, Pd/C
30. What is the structure for the compound whose IUPAC name is pentyl 2-
methylbutanoate?
A) Propionyl phenol C) Phenol propanoate

B) Phenyl propanoate D) Phenyl acetate
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38. What is the missing reagent in the reaction below?
A) acetic acid B) NaOMe C) SOCl2 D) pyridine
39. Which of the following reaction conditions can be used to synthesize an ester
(RCOOR')?
A) RCOCl + R'NH2 + pyridine C) RCOOH + R'OH + OH-
B) RCOOH + R'OH + H+ D) RCONH2 + R'OH
40. Rank the following compounds in order of increasing reactivity in nucleophilic acyl
substitution.
A) I > II > III B) III > II > I C) II > III > I D) III > I > II
41. Draw the structure of N-phenyl acetamide.
42. Which of the following substrates cannot be used as an immediate precursor to

synthesize an ester?
43. From the list below, pick the compound that does not react with acetyl chloride.
A) Isopropyl alcohol B) Benzoic acid C) Ammonia D) Triethyl amine
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44. Which of the following statements about amides is true?

A) Amides react with methyl alcohol in the presence of an acid catalyst to form an
ester.
B) Amides are hydrolyzed in acid or base to form carboxylic acids or carboxylate
anions.
C) Amides react with thionyl chloride to form the acid chloride.
D) Amides do not react under any conditions. They are inert compounds.
45. n-Butanenitrile will undergo all of the following listed reactions except one. Which
reaction listed is not true for n-butanenitrile?
A) n-Butane nitrile will react with ethylmagnesium bromide to form an alcohol.
B) n-Butanenitrile with be reduced to butyl amine in the presence of LiAlH4 with an
aqueous work-up.
C) n-Butanenitrile is hydrolyzed in the presence of acid to form butanoic acid.
D) n-Butanenitrile is reduced with DIBAL-H to form n-butanal.
46. An unknown compound has a sharp, medium peak at 2250 cm-1. The unknown
compound is probably
A) an alkane B) an aldehyde C) an alkene D) a nitrile
47. All of the following contain sp2 hybridized atoms in their functional group except
A) a carboxylic acid B) a nitrile C) an aldehyde D) an anhydride
Chapter 23: Substitution Reactions of Carbonyl Compounds at

the Alpha-Carbon
1. Which is the more stable form of acetophenone?
A) Only I B) Only II C) Only III D) I and II are equally stable
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Chapter 19: Carboxylic Acids and The Acidity of The O-H Bond

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Chapter 1: Structure and Bonding

51. What is the product of the following reaction?

1. What is the hybridization of the carbon atom in a carboxy group?

3. What two groups make up the carboxylic acid group (RCOOH)?

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

A) 4-Isopropyl-3-methylbutanoic acid C) 3,5-Dimethylhexanoic acid

5. What is the correct IUPAC name of the following compound?

6. What is the correct IUPAC name of the following compound?

7. What is the correct IUPAC name of the following compound?

8. What is the common name of the following compound?

A) -Methylbutyric acid C) -Methylvaleric acid

9. What is the common name of the following compound?

A) ,-Dimethoxyvaleric acid C) 2,3-Dimethoxycaproic acid

10. What is the common name of the following compound?

11. What is the common name of the following compound?

A) Propanedioic acid C) Malonic acid

12. What is the correct IUPAC name of the following compound?

A) (E)-2-Hexenoic acid C) (E)-4-Hexenoic acid

13. What is the correct IUPAC name of the following compound?

A) 2-Methoxypentanoic acid C) 4-Methoxybutanoic acid

14. Which of the following is the structure of oxalic acid?

A) Potassium propanoate C) Potassium propanoic

16. Which of the following is the most polar organic compound?

A) I < II < III < IV C) III < II < IV < I

A) I > II > III > IV C) I > II > IV > III

A) I < II < III < IV C) I < III < II < IV

A) PCC, CH2Cl2 C) [1] O3; [2] H2O

A) HCOOH B) HCOH C) CO2 D) CO

A) I < II < III < IV C) III < IV < II < I

A) Ha < Hb < Hc < Hd C) Hd < Ha < Hc < Hb

A) IV > III > I > II C) II > I > IV > III

A) II < III < I < IV C) IV < III < I < II

A) III < II < IV < I C) I < IV < II < III

A) IV > III > II > I C) I > II > III > IV

A) I < II < III < IV C) IV < I < II < III

A) III > IV > I > II C) I > II > III > IV

A) III < I < II < IV C) III < II < I < IV

41. What is the overall charge of the amino acid, alanine, at pH = 2?

43. What is the overall charge of the amino acid, alanine, at pH = 7?

Chapter 20: Introduction to Carbonyl Chemistry;

3. What are the two steps in a nucleophilic addition mechanism?

5. Why are ketones less reactive than aldehydes?

45. What is the product of the following reaction?

Chapter 22: Carboxylic Acids and Derivatives

1. Which of the following is a lactam?

3. What is the IUPAC name for the following compound?

A) methyl 3-methylbutanamide C) N-methyl 3-methylhexanamide

B) 5-methylhexanamide D) N-methyl 3-methylbutanamide

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

A) 4-fluoro-3-methylbenzoate C) 3-methyl-4-fluorobenzoic acid

5. What is the structure for acetic propanoic anhydride?

6. What is the structure for ethyl 4-chlorobenzoate?

7. What is the structure for 3-cyanocyclopentanone?

8. What is the IUPAC name for the following compound?

9. Where is the carbonyl absorption found in the IR spectrum of a simple ester?

13. Which structure is consistent with the following 1H NMR spectrum?

A) ethyl acetate C) 3,3-dimethyl-2-pentanone

B) 2-propanone D) ethyl 2,2-dimethylpropionate