Question 1

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 A

Question 2

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 3

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 B

Question 4

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 5

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 6

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 7

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 8

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 9

What reagents are necessary to perform the following reaction?

Accepted Answer

A) H2O,H+ 
B) LiAlH4,H2O 
C) DIBAL-H,H2O 
D) CH3MgBr,H2O 
A) H2O,H+ 
B) LiAlH4,H2O 
C) DIBAL-H,H2O 
D) CH3MgBr,H2O

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

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 12

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 13

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 14

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 15

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 16

What reagents are necessary to perform the following reaction?

Accepted Answer

A) H2O,H+ 
B) LiAlH4,H2O 
C) DIBAL-H,H2O 
D) CH3MgBr,H2O 
A) H2O,H+ 
B) LiAlH4,H2O 
C) DIBAL-H,H2O 
D) CH3MgBr,H2O

Question 17

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 18

What reagents are necessary to perform the following reaction?

Accepted Answer

A) H2O,H+ 
B) LiAlH4,H2O 
C) DIBAL-H,H2O 
D) CH3MgBr,H2O 
A) H2O,H+ 
B) LiAlH4,H2O 
C) DIBAL-H,H2O 
D) CH3MgBr,H2O

Question 19

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 a 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 a 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 a 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 a 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 a 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 a 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 a 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 a carbon to the carboxy group.

Question 20

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.

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

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.

Which of the following is the structure of oxalic acid?

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

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

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

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

What is the correct IUPAC name of the following compound?

What reagents are necessary to perform the following reaction?

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

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

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?

What is the correct IUPAC name of the following compound?

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

What reagents are necessary to perform the following reaction?

What is the correct IUPAC name of the following compound?

What reagents are necessary to perform the following reaction?

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

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

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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

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

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