Question 1

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 C

Question 2

In the presence of strong acids, which of the oxygen atoms on the carboxyl group is preferentially protonated and why?

Accepted Answer

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. 
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. A

Question 3

What is the hybridization of the carbon atom in a carboxy group?

Accepted Answer

A) sp 
B) sp2 
C) sp3 
D) p 
A) sp 
B) sp2 
C) sp3 
D) p B

Question 4

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 5

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 6

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

Question 7

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 8

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 9

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 10

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 11

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 12

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 13

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 14

Which of the following is the structure of oxalic acid?

Accepted Answer

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

Question 15

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 16

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 17

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 18

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 19

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

Question 20

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

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

What is the common name of the following compound?

In the presence of strong acids, which of the oxygen atoms on the carboxyl group is preferentially protonated and why?

What is the hybridization of the carbon atom in a carboxy group?

What is the correct IUPAC name of the following compound?

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

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

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

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

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

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.

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

What is the correct IUPAC name of the following compound?

Which of the following is the structure of oxalic acid?

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

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

Which of the following compounds is most basic?

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

What is the correct IUPAC name of the following compound?

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

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