Question 1

Which of the following reagents can accomplish the transformation below?

Accepted Answer

A)  PCC, CH2Cl2 
B)  [1] LiAlH4, THF; [2] H2O 
C)  [1] O3; [2] H2O 
D)  K2Cr2O7, H2SO4, H2O 
A)  PCC, CH2Cl2 
B)  [1] LiAlH4, THF; [2] H2O 
C)  [1] O3; [2] H2O 
D)  K2Cr2O7, H2SO4, H2O

Question 2

Arrange the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.

Accepted Answer

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

Question 3

Arrange the following compounds in order of increasing water solubility, putting the least soluble compound first.

Accepted Answer

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

Question 4

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 5

What is the common name of the following compound?

Accepted Answer

A)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-Dimethoxyvaleric acid" 
B)  "2,3-Dimethoxyvaleric acid" 
C)  "2,3-Dimethoxycaproic acid" 
D)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-Dimethoxycaproic acid" 
A)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-Dimethoxyvaleric acid" 
B)  "2,3-Dimethoxyvaleric acid" 
C)  "2,3-Dimethoxycaproic acid" 
D)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-Dimethoxycaproic acid"

Question 6

What is the common name of the following compound?

Accepted Answer

A)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-Dimethyl-F1F1F1S1F1F1F10-fluorobutyric acid" 
B)  "F1F1F1S1F1F1F10-Fluoro-F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-dimethylbutyric acid" 
C)  "F1F1F1S1F1F1F10-Fluoro-F1F1F1S1F1F1F10,F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-trimethylpropionic acid" 
D)  "F1F1F1S1F1F1F10-Fluoro-F1F1F1S1F1F1F10,F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-trimethylbutyric acid" 
A)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-Dimethyl-F1F1F1S1F1F1F10-fluorobutyric acid" 
B)  "F1F1F1S1F1F1F10-Fluoro-F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-dimethylbutyric acid" 
C)  "F1F1F1S1F1F1F10-Fluoro-F1F1F1S1F1F1F10,F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-trimethylpropionic acid" 
D)  "F1F1F1S1F1F1F10-Fluoro-F1F1F1S1F1F1F10,F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-trimethylbutyric 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

Arrange the following compounds in order of decreasing water solubility, putting the most soluble compound first.

Accepted Answer

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

Question 9

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 10

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

Accepted Answer

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

Question 11

Where do the two noteworthy peaks of carboxylic acids appear in 1HNMR spectra?

Accepted Answer

A)  Between 10 and 12 ppm for the OH proton and 2-2.5 ppm for the protons on the F1F1F1S1F1F1F10 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 F1F1F1S1F1F1F10 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 F1F1F1S1F1F1F10 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 F1F1F1S1F1F1F10 carbon to the carboxy group. 
A)  Between 10 and 12 ppm for the OH proton and 2-2.5 ppm for the protons on the F1F1F1S1F1F1F10 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 F1F1F1S1F1F1F10 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 F1F1F1S1F1F1F10 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 F1F1F1S1F1F1F10 carbon to the carboxy group.

Question 12

What is the correct IUPAC name of the following compound?

Accepted Answer

A)  3,4-Dimethylcyclohexanoic acid 
B)  3,4-Dimethylcyclohexanecarboxylic acid 
C)  4,5-Dimethylcyclohexanecarboxylic acid 
D)  1,2-Dimethylcyclohexanecarboxylic acid 
A)  3,4-Dimethylcyclohexanoic acid 
B)  3,4-Dimethylcyclohexanecarboxylic acid 
C)  4,5-Dimethylcyclohexanecarboxylic acid 
D)  1,2-Dimethylcyclohexanecarboxylic acid

Question 13

As applied to the chemistry of amino acids, what is the definition for the isoelectric point?

Accepted Answer

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. 
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.

Question 14

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

Accepted Answer

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

Question 15

Which of the following cannot be the starting material for the following reaction?

Accepted Answer

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

Question 16

What is the common name of the following compound?

Accepted Answer

A)  Propanedioic acid 
B)  1,3-propanedicarboxylic acid 
C)  Malonic acid 
D)  Succinic acid 
A)  Propanedioic acid 
B)  1,3-propanedicarboxylic acid 
C)  Malonic acid 
D)  Succinic acid

Question 17

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.

Question 18

What physical property and reaction type are used by extraction as useful techniques to separate and purify mixtures of compounds?

Accepted Answer

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. 
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.

Question 19

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 20

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

Accepted Answer

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

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

Which of the following reagents can accomplish the transformation below?

Arrange the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.

Arrange the following compounds in order of increasing water solubility, putting the least soluble compound first.

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

What is the common name of the following compound?

What is the common name of the following compound?

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

Arrange the following compounds in order of decreasing water solubility, putting the most soluble compound first.

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

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

Where do the two noteworthy peaks of carboxylic acids appear in 1HNMR spectra?

What is the correct IUPAC name of the following compound?

As applied to the chemistry of amino acids, what is the definition for the isoelectric point?

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

Which of the following cannot be the starting material for the following reaction?

What is the common name of the following compound?

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

What physical property and reaction type are used by extraction as useful techniques to separate and purify mixtures of compounds?

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

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

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

Where do the two noteworthy peaks of carboxylic acids appear in ¹HNMR spectra?