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

Question 2

Give the IUPAC name of the following compound.

Accepted Answer

A) R-2-methylpentanenitrile 
B) S-2-methylpentanenitrile 
C) R-2-nitrilehexane 
D) S-2-nitrilehexane 
A) R-2-methylpentanenitrile 
B) S-2-methylpentanenitrile 
C) R-2-nitrilehexane 
D) S-2-nitrilehexane

Question 3

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

Accepted Answer

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

Question 4

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 5

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 6

What is the common name of the following compound?

Accepted Answer

A) a,b-Dimethoxyvaleric acid 
B) 2,3-Dimethoxyvaleric acid 
C) 2,3-Dimethoxycaproic acid 
D) a,b-Dimethoxycaproic acid 
A) a,b-Dimethoxyvaleric acid 
B) 2,3-Dimethoxyvaleric acid 
C) 2,3-Dimethoxycaproic acid 
D) a,b-Dimethoxycaproic acid

Question 7

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 8

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 9

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 10

What is the common name of the following compound?

Accepted Answer

A) a-Methylbutyric acid 
B) a-Propylpropionic acid 
C) a-Methylvaleric acid 
D) a-Methylcaproic acid 
A) a-Methylbutyric acid 
B) a-Propylpropionic acid 
C) a-Methylvaleric acid 
D) a-Methylcaproic acid

Question 11

Which of the following compounds is most basic?

Accepted Answer

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

Question 12

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

Question 13

What is the correct IUPAC name of the following compound?

Accepted Answer

A) 4-Isopropyl-3-methylbutanoic acid 
B) 2,4-Dimethylhexanoic acid 
C) 3,5-Dimethylhexanoic acid 
D) 3,5-Dimethy-1-hexanoic acid 
A) 4-Isopropyl-3-methylbutanoic acid 
B) 2,4-Dimethylhexanoic acid 
C) 3,5-Dimethylhexanoic acid 
D) 3,5-Dimethy-1-hexanoic acid

Question 14

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 15

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 16

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 17

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 18

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 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 two strong absorptions are characteristic of the IR spectrum of carboxylic acids?

Accepted Answer

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. 
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.

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

Which of the following is the most polar organic compound?

Give the IUPAC name of the following compound.

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

Why is pure acetic acid often called glacial acetic acid?

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

What is the common name of the following compound?

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

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

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?

Which of the following compounds is most basic?

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

What is the correct IUPAC name of the following compound?

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 = 2?

What is the common name of the following compound?

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

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

What is the correct IUPAC name of the following compound?

What two strong absorptions are characteristic of the IR spectrum of carboxylic acids?

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 and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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)?

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