Question 1

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 2

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 3

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 4

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 5

What is the correct IUPAC name of the following compound?

Accepted Answer

A) 3,5,5-Trimethylcyclohexanecarboxylic acid 
B) 3,3,5-Trimethylcyclohexanecarboxylic acid 
C) 3,3,5-Trimethylcyclohexanoic acid 
D) 3,5,5-Trimethylcyclohexanoic acid 
A) 3,5,5-Trimethylcyclohexanecarboxylic acid 
B) 3,3,5-Trimethylcyclohexanecarboxylic acid 
C) 3,3,5-Trimethylcyclohexanoic acid 
D) 3,5,5-Trimethylcyclohexanoic acid

Question 6

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 7

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 8

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 9

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

Accepted Answer

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

Question 10

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 11

Give the IUPAC name for the following compound.

Accepted Answer

A) (E,R)-2-bromo-3-pentenoic acid 
B) (Z,R)-2-bromo-3-pentenoic acid 
C) (E,S)-2-bromo-3-pentenoic acid 
D) (Z,S)-2-bromo-3-pentenoic acid 
A) (E,R)-2-bromo-3-pentenoic acid 
B) (Z,R)-2-bromo-3-pentenoic acid 
C) (E,S)-2-bromo-3-pentenoic acid 
D) (Z,S)-2-bromo-3-pentenoic acid

Question 12

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 13

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.

Question 14

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 15

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 16

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 17

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 18

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 19

Give the IUPAC name for the following compound.

Accepted Answer

A) (E,R)-2-methyl-3-pentenenitrile 
B) (E,S)-2-methyl-3-pentenenitrile 
C) (Z,R)-2-methyl-3-pentenenitrile 
D) (Z,S)-2-methyl-3-pentenenitrile 
A) (E,R)-2-methyl-3-pentenenitrile 
B) (E,S)-2-methyl-3-pentenenitrile 
C) (Z,R)-2-methyl-3-pentenenitrile 
D) (Z,S)-2-methyl-3-pentenenitrile

Question 20

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

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

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

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

Which of the following is the most polar organic compound?

What is the common name of the following compound?

What is the correct IUPAC name of the following compound?

Give the IUPAC name of the following compound.

Which of the following reagents can accomplish the transformation below?

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

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

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

Give the IUPAC name for the following compound.

What is the correct IUPAC 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 common name of the following compound?

What is the common name of the following compound?

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

What is the common name of the following compound?

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

Give the IUPAC name for the following compound.

What reagents are necessary to perform the following reaction?

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

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

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