Question 1

Which of the following is the most polar organic compound?

Accepted Answer

A)  CH3CH2CH2CH3 
B)  CH3CH2CHO 
C)  CH3CH2CH2OH 
D)  CH3COOH 
A)  CH3CH2CH2CH3 
B)  CH3CH2CHO 
C)  CH3CH2CH2OH 
D)  CH3COOH D

Question 2

Why is pure acetic acid often called glacial acetic acid?

Accepted Answer

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. 
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. C

Question 3

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

Accepted Answer

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

Question 4

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

Accepted Answer

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

Question 5

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

Accepted Answer

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

Question 6

What would happen if a mixture of benzoic acid (C6H5COOH) and NaCl is added to a separatory funnel containing H2O and CH2Cl2?

Accepted Answer

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. 
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.

Question 7

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

Accepted Answer

A)  Carbon dioxide and hydrogen 
B)  Carbonyl and hydroxyl 
C)  Carbon monoxide and hydroxyl 
D)  Carbonyl oxide and hydrogen 
A)  Carbon dioxide and hydrogen 
B)  Carbonyl and hydroxyl 
C)  Carbon monoxide and hydroxyl 
D)  Carbonyl oxide and hydrogen

Question 8

What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH2Cl2 is treated with aqueous NaOH solution?

Accepted Answer

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. 
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.

Question 9

Which of the following structures is the major contributor to the resonance hybrid of the phenoxide anion?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 10

What is the correct IUPAC name of the following compound?

Accepted Answer

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

Question 11

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

Accepted Answer

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

Question 12

Which of the following bases are strong enough to significantly deprotonate ethanol, CH3CH2OH (pKa = 16)?

Accepted Answer

A)  NaOCH3 
B)  NaOH 
C)  NaH 
D)  NaOCH2CH3 
A)  NaOCH3 
B)  NaOH 
C)  NaH 
D)  NaOCH2CH3

Question 13

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

Accepted Answer

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

Question 14

What is the correct IUPAC name of the following compound?

Accepted Answer

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)  3,5,5-Trimethylcyclohexanecarboxylic acid 
B)  3,3,5-Trimethylcyclohexanecarboxylic acid 
C)  3,3,5-Trimethylcyclohexanoic acid 
D)  3,5,5-Trimethylcyclohexanoic acid

Question 15

Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic.

Accepted Answer

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

Question 16

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

Accepted Answer

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

Question 17

What is the common name of the following compound?

Accepted Answer

A)  "F1F1F1S1F1F1F10-Methylbutyric acid" 
B)  "F1F1F1S1F1F1F10-Propylpropionic acid" 
C)  "F1F1F1S1F1F1F10-Methylvaleric acid" 
D)  "F1F1F1S1F1F1F10-Methylcaproic acid" 
A)  "F1F1F1S1F1F1F10-Methylbutyric acid" 
B)  "F1F1F1S1F1F1F10-Propylpropionic acid" 
C)  "F1F1F1S1F1F1F10-Methylvaleric acid" 
D)  "F1F1F1S1F1F1F10-Methylcaproic acid"

Question 18

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

Accepted Answer

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

Question 19

What is the correct IUPAC name of the following compound?

Accepted Answer

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)  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

Question 20

What is the correct IUPAC name of the following compound?

Accepted Answer

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

Exam 19: Carboxylic Acids and the Acidity of the O-H Bond

Which of the following is the most polar organic compound?

Why is pure acetic acid often called glacial acetic acid?

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

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

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

What would happen if a mixture of benzoic acid (C6H5COOH) and NaCl is added to a separatory funnel containing H2O and CH2Cl2?

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

What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH2Cl2 is treated with aqueous NaOH solution?

Which of the following structures is the major contributor to the resonance hybrid of the phenoxide anion?

What is the correct IUPAC name of the following compound?

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

Which of the following bases are strong enough to significantly deprotonate ethanol, CH3CH2OH (pKa = 16)?

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

What is the correct IUPAC name of the following compound?

Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic.

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

What is the common name of the following compound?

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

What is the correct IUPAC name of the following compound?

What is the correct IUPAC name of the following compound?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

What would happen if a mixture of benzoic acid (C₆H₅COOH) and NaCl is added to a separatory funnel containing H₂O and CH₂Cl₂?

What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH₂Cl₂ is treated with aqueous NaOH solution?

Which of the following bases are strong enough to significantly deprotonate ethanol, CH₃CH₂OH (pKa = 16)?

Rank the labeled protons (H_a-H_d) in order of increasing acidity, starting with the least acidic.