Ch19 Carboxylic Acids And The Test Questions & Answers

Organic Chemistry, 6e (Smith)

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-character that shortens the C-O bond in the carboxylic acid.

D) The carbon in the carboxylic acid is sp2 hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid.

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

A) Carbon dioxide and hydrogen

B) Carbonyl and hydroxyl

C) Carbon monoxide and hydroxyl

D) Carbonyl oxide and hydrogen

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

A) 4-Isopropyl-3-methylbutanoic acid

B) 2,4-Dimethylhexanoic acid

C) 3,5-Dimethylhexanoic acid

D) 3,5-Dimethy-1-hexanoic acid

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

A) 3,5,5-Trimethylcyclohexanecarboxylic acid

B) 3,3,5-Trimethylcyclohexanecarboxylic acid

C) 3,3,5-Trimethylcyclohexanoic acid

D) 3,5,5-Trimethylcyclohexanoic acid

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

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

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

A) 3,4-Dimethylcyclohexanoic acid

B) 3,4-Dimethylcyclohexanecarboxylic acid

C) 4,5-Dimethylcyclohexanecarboxylic acid

D) 1,2-Dimethylcyclohexanecarboxylic acid

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

A) a-Methylbutyric acid

B) a-Propylpropionic acid

C) a-Methylvaleric acid

D) a-Methylcaproic acid

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

A) a,b-Dimethoxyvaleric acid

B) 2,3-Dimethoxyvaleric acid

C) 2,3-Dimethoxycaproic acid

D) a,b-Dimethoxycaproic acid

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

A) b,b-Dimethyl-a-fluorobutyric acid

B) a-Fluoro-b,b-dimethylbutyric acid

C) a-Fluoro-b,b,b-trimethylpropionic acid

D) a-Fluoro-b,b,b-trimethylbutyric acid

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

A) Propanedioic acid

B) 1,3-Propanedicarboxylic acid

C) Malonic acid

D) Succinic acid

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

A) (E)-2-Hexenoic acid

B) (Z)-2-Hexenoic acid

C) (E)-4-Hexenoic acid

D) (Z)-4-Hexenoic acid

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

A) 2-Methoxypentanoic acid

B) 2-Methoxybutanoic acid

C) 4-Methoxybutanoic acid

D) 4-Methoxypentanoic acid

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

A) I

B) II

C) III

D) IV

15) Which of the following is the correct IUPAC name for the following structure?

A) Potassium propanoate

B) Butanoic potassium

C) Potassium propanoic

D) Potassium butanoate

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

A) CH3CH2CH2CH3

B) CH3CH2CHO

C) CH3CH2CH2OH

D) CH3COOH

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

B) I < IV < II < III

C) III < II < IV < I

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

B) I > IV > II > III

C) I > II > IV > 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

B) II < I < III < IV

C) I < III < II < 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 a carbon to the carboxy group.

B) Between 6 and 9 ppm for the OH proton and 2-2.5 ppm for the protons on the a carbon to the carboxy group.

C) Between 10 and 12 ppm for the OH proton and 1-1.5 ppm for the protons on the a carbon to the carboxy group.

D) Between 6 and 9 ppm for the OH proton and 1-1.5 ppm for the protons on the a carbon to the carboxy group.

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

B) [1] LiAlH4, THF; [2] H2O

C) [1] O3; [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?

A) I

B) II

C) III

D) IV

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?

A) I

B) II

C) III

D) IV

28) Arrange the following compounds in order of increasing acidity, putting the least acidic first.

A) I < II < III < IV

B) IV < III < II < I

C) III < IV < 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

B) Hb < Hc < Ha < Hd

C) Hd < Ha < Hc < Hb

D) Hb < Hc < Hd < Ha

31) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > III > I > II

B) IV > II > I > III

C) II > I > IV > 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

B) II < I < III < IV

C) IV < III < I < II

D) IV < I < II < III

33) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) III < II < IV < I

B) III < IV < II < I

C) I < IV < II < III

D) I < II < III < IV

34) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > III > II > I

B) IV > I > III > II

C) I > II > III > IV

D) IV > II > III > I

35) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) I < II < III < IV

B) III < II < I < IV

C) IV < I < II < III

D) I < IV < III < II

36) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) III > IV > I > II

B) IV > III > I > II

C) I > II > III > IV

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

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.

40) What is the overall charge of the amino acid, alanine, at pH = 2?

A) + 1

B) – 1

C) No overall charge

D) + 2

41) What is the overall charge of the amino acid, alanine, at pH = 10?

A) + 1

B) – 1

C) No overall charge

D) – 2

42) What is the overall charge of the amino acid, alanine, at pH = 7?

A) + 1

B) – 1

C) No overall charge

D) + 2

43) 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.

44) Which of the following compounds is most basic?

A) I

B) II

C) III

D) IV

45) Which of the following compounds is least basic?

A) I

B) II

C) III

D) IV

46) Give the IUPAC name for the following compound.

A) (E,R)-2-bromo-3-pentenoic acid

B) (Z,R)-2-bromo-3-pentenoic acid

C) (E,S)-2-bromo-3-pentenoic acid

D) (Z,S)-2-bromo-3-pentenoic acid

47) Give the IUPAC name for the following compound.

A) (E,R)-2-bromo-3-pentenoic acid

B) (Z,R)-2-bromo-3-pentenoic acid

C) (E,S)-2-bromo-3-pentenoic acid

D) (Z,S)-2-bromo-3-pentenoic acid

48) Give the IUPAC name of the following compound.

A) R-2-methylpentanenitrile

B) S-2-methylpentanenitrile

C) R-2-nitrilehexane

D) S-2-nitrilehexane

49) Give the IUPAC name for the following compound.

A) (E,R)-2-methyl-3-pentenenitrile

B) (E,S)-2-methyl-3-pentenenitrile

C) (Z,R)-2-methyl-3-pentenenitrile

D) (Z,S)-2-methyl-3-pentenenitrile

50) What reagents are necessary to perform the following reaction?

A) H2O, H+

B) LiAlH4, H2O

C) DIBAL-H, H2O

D) CH3MgBr, H2O

51) What reagents are necessary to perform the following reaction?

A) H2O, H+

B) LiAlH4, H2O

C) DIBAL-H, H2O

D) CH3MgBr, H2O

52) What reagents are necessary to perform the following reaction?

A) H2O, H+

B) LiAlH4, H2O

C) DIBAL-H, H2O

D) CH3MgBr, H2O

53) What reagents are necessary to perform the following reaction?

A) H2O, H+

B) LiAlH4, H2O

C) DIBAL-H, H2O

D) CH3MgBr, H2O