Question 1

Which of the following statements about a crown ether-cation complex is not true?

Accepted Answer

A) It is a host-guest complex. 
B) The crown ether is the guest and the cation is the host. 
C) The crown ether is the host and the cation is the guest. 
D) The host-guest complex is soluble in nonpolar solvents. 
A) It is a host-guest complex. 
B) The crown ether is the guest and the cation is the host. 
C) The crown ether is the host and the cation is the guest. 
D) The host-guest complex is soluble in nonpolar solvents. B

Question 2

Which of the following compounds is (are)symmetrical ethers?

Accepted Answer

A) Only I 
B) Only IV 
C) Only III and IV 
D) Only I,III,and IV 
A) Only I 
B) Only IV 
C) Only III and IV 
D) Only I,III,and IV B

Question 3

Which of the following would be a reasonable synthesis of 2-butanol?

Accepted Answer

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

Question 4

What is the major organic product(s)obtained in the following reaction?

Accepted Answer

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

Question 5

Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4,putting the least reactive first.

Accepted Answer

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

Question 6

What is the IUPAC name of the following compound?

Accepted Answer

A) (2R,4R)-4-chloro-2-pentanol 
B) (2R,4S)-4-chloro-2-pentanol 
C) (2S,4R)-4-chloro-2-pentanol 
D) (2S,4S)-4-chloro-2-pentanol 
A) (2R,4R)-4-chloro-2-pentanol 
B) (2R,4S)-4-chloro-2-pentanol 
C) (2S,4R)-4-chloro-2-pentanol 
D) (2S,4S)-4-chloro-2-pentanol

Question 7

Which of the following compounds has the highest boiling point?

Accepted Answer

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

Question 8

Which of the following compounds are epoxides?

Accepted Answer

A) Only I and III 
B) Only III and IV 
C) Only I,III,and IV 
D) I,II,III,and IV 
A) Only I and III 
B) Only III and IV 
C) Only I,III,and IV 
D) I,II,III,and IV

Question 9

Determine the product in the following reaction (ignoring possible stereoisomers).

Accepted Answer

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

Question 10

What is the major product of the following reaction?

Accepted Answer

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

Question 11

Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements?

Accepted Answer

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

Question 12

Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?

Accepted Answer

A) Sodium methoxide and tert-butyl bromide. 
B) Sodium tert-butoxide and iodomethane. 
C) Methanol and tert-butyl alcohol in the presence of KOH. 
D) Iodomethane and tert-butyl bromide in the presence of KOH. 
A) Sodium methoxide and tert-butyl bromide. 
B) Sodium tert-butoxide and iodomethane. 
C) Methanol and tert-butyl alcohol in the presence of KOH. 
D) Iodomethane and tert-butyl bromide in the presence of KOH.

Question 13

Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?

Accepted Answer

A) Bromobenzene and sodium methoxide 
B) Phenol and sodium methoxide 
C) Bromobenzene and bromomethane 
D) Sodium phenoxide and bromomethane 
A) Bromobenzene and sodium methoxide 
B) Phenol and sodium methoxide 
C) Bromobenzene and bromomethane 
D) Sodium phenoxide and bromomethane

Question 14

What is the IUPAC of the following compound?

Accepted Answer

A) Ethoxyoctane 
B) 5-Ethoxyoctane 
C) 4-Ethoxyoctane 
D) Ethyl octyl ether 
A) Ethoxyoctane 
B) 5-Ethoxyoctane 
C) 4-Ethoxyoctane 
D) Ethyl octyl ether

Question 15

What is the common name of the following compound?

Accepted Answer

A) Isobutyl isopropyl ether 
B) Diisobutyl ether 
C) Di-sec-butyl ether 
D) Diisopropyl ether 
A) Isobutyl isopropyl ether 
B) Diisobutyl ether 
C) Di-sec-butyl ether 
D) Diisopropyl ether

Question 16

Which of the following compounds are ethers?

Accepted Answer

A) Only I and II 
B) Only III and IV 
C) Only I,II,and III 
D) I,II,III,and IV 
A) Only I and II 
B) Only III and IV 
C) Only I,II,and III 
D) I,II,III,and IV

Question 17

What is the IUPAC name of the following compound?

Accepted Answer

A) 3-Ethyl-5-methylcyclohexanethiol 
B) 3-Ethyl-5-methylcyclohexane-1-thiol 
C) 5-Ethyl-2-methylcyclohexanethiol 
D) 5-Ethyl-2-methylcyclohexylthiol 
A) 3-Ethyl-5-methylcyclohexanethiol 
B) 3-Ethyl-5-methylcyclohexane-1-thiol 
C) 5-Ethyl-2-methylcyclohexanethiol 
D) 5-Ethyl-2-methylcyclohexylthiol

Question 18

What is the IUPAC name of the following compound?

Accepted Answer

A) 5-Ethylthio-4-isopropylpentane 
B) 1-Ethylthio-3-methyl-2-propylbutane 
C) 1-Ethylthio-2-isopropylpentane 
D) Isooctylthioethane 
A) 5-Ethylthio-4-isopropylpentane 
B) 1-Ethylthio-3-methyl-2-propylbutane 
C) 1-Ethylthio-2-isopropylpentane 
D) Isooctylthioethane

Question 19

What is the major alkene formed when compound A is dehydrated with H2SO4?

Accepted Answer

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

Question 20

What is the common name of the following compound?

Accepted Answer

A) Methyl sec-butyl ether 
B) Isobutyl methyl ether 
C) sec-Butyl methyl ether 
D) Butyl methyl ether 
A) Methyl sec-butyl ether 
B) Isobutyl methyl ether 
C) sec-Butyl methyl ether 
D) Butyl methyl ether

Exam 9: Alcohols,ethers,and Related Compounds

Which of the following statements about a crown ether-cation complex is not true?

Which of the following compounds is (are)symmetrical ethers?

Which of the following would be a reasonable synthesis of 2-butanol?

What is the major organic product(s)obtained in the following reaction?

Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4,putting the least reactive first.

What is the IUPAC name of the following compound?

Which of the following compounds has the highest boiling point?

Which of the following compounds are epoxides?

Determine the product in the following reaction (ignoring possible stereoisomers).

What is the major product of the following reaction?

Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements?

Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?

Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?

What is the IUPAC of the following compound?

What is the common name of the following compound?

Which of the following compounds are ethers?

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

What is the major alkene formed when compound A is dehydrated with H2SO4?

What is the common name of the following compound?

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

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 the Acidity of the O-H Bond

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

Rank the alcohols in order of increasing reactivity when dehydrated with H₂SO₄,putting the least reactive first.

What is the major alkene formed when compound A is dehydrated with H₂SO₄?