Question 1

Which of the following compounds is least basic?

Accepted Answer

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

Question 2

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 3

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 4

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 5

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 6

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 7

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.

Question 8

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

Accepted Answer

A) Potassium propanoate 
B) Butanoic potassium 
C) Potassium propanoic 
D) Potassium butanoate 
A) Potassium propanoate 
B) Butanoic potassium 
C) Potassium propanoic 
D) Potassium butanoate

Question 9

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 10

Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an alcohol?

Accepted Answer

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. 
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.

Question 11

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 12

What is the common name of the following compound?

Accepted Answer

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 
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

Question 13

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 14

What is the other product formed in the oxidation of the following terminal alkyne?

Accepted Answer

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

Question 15

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

Question 16

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

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

Which of the following compounds is least basic?

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

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

What is the correct IUPAC name of the following compound?

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

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

Why is pure acetic acid often called glacial acetic acid?

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

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

Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an alcohol?

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

What is the common name of the following compound?

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

What is the other product formed in the oxidation of the following terminal alkyne?

Which of the following is the most polar organic compound?

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

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 Related Compounds

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry;

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

Synthetic Polymers

Lipids

Filters

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

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

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