Question 1

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

A) (S)-2-Methoxypentane 
B) (R)-2-Methoxypentane 
C) (±)-2-Methoxypentane 
D) trans-2-Butene 
A) (S)-2-Methoxypentane 
B) (R)-2-Methoxypentane 
C) (±)-2-Methoxypentane 
D) trans-2-Butene

Question 2

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 3

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 4

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 5

Which of the following compounds is (are)primary alcohols?

Accepted Answer

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

Question 6

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 7

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

Accepted Answer

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

Question 8

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 9

Determine the product(s)of the following reaction.

Accepted Answer

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

Question 10

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 11

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 12

Which of the following would be a reasonable synthesis of 1-butanol?

Accepted Answer

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

Question 13

What is the major organic product of the following reaction?

Accepted Answer

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

Question 14

What is the IUPAC of the following compound?

Accepted Answer

A) 3,3,6-Trimethylcyclohexanol 
B) 2,5,5-Trimethylcyclohexanol 
C) 1,4,4-Trimethyl-2-cyclohexanol 
D) 1,1,4-Trimethyl-2-cyclohexanol 
A) 3,3,6-Trimethylcyclohexanol 
B) 2,5,5-Trimethylcyclohexanol 
C) 1,4,4-Trimethyl-2-cyclohexanol 
D) 1,1,4-Trimethyl-2-cyclohexanol

Question 15

Determine the product(s)of the following reaction.

Accepted Answer

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

Question 16

What is the IUPAC of the following compound?

Accepted Answer

A) 1,2-Epoxy-2-methylcyclopentane 
B) 1,2-Epoxy-1-methylcyclopentane 
C) 1,2-Epoxy-1-methylpentane 
D) 1,2-Epoxy-2-methylpentane 
A) 1,2-Epoxy-2-methylcyclopentane 
B) 1,2-Epoxy-1-methylcyclopentane 
C) 1,2-Epoxy-1-methylpentane 
D) 1,2-Epoxy-2-methylpentane

Question 17

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 18

What is the major alkene formed when compound A is dehydrated with POCl3 and pyridine?

Accepted Answer

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

Question 19

What is the IUPAC of the following compound?

Accepted Answer

A) 1,2-Epoxy-4-methylcyclohexane 
B) 3,4-Epoxy-1-methylcyclohexane 
C) 1,2-Epoxy-3-methylcyclohexane 
D) 1,2-Epoxy-5-methylcyclohexane 
A) 1,2-Epoxy-4-methylcyclohexane 
B) 3,4-Epoxy-1-methylcyclohexane 
C) 1,2-Epoxy-3-methylcyclohexane 
D) 1,2-Epoxy-5-methylcyclohexane

Question 20

What is the IUPAC name of the following compound?

Accepted Answer

A) R-2-methoxy-5,5-dimethylhexane 
B) S-2-methoxy-5,5-dimethylhexane 
C) R-5-methoxy-2,2-dimethylhexane 
D) S-5-methoxy-2,2-dimethylhexane 
A) R-2-methoxy-5,5-dimethylhexane 
B) S-2-methoxy-5,5-dimethylhexane 
C) R-5-methoxy-2,2-dimethylhexane 
D) S-5-methoxy-2,2-dimethylhexane

Exam 9: Alcohols,ethers,and Related Compounds

What is the major organic product obtained from the following sequence of reactions?

What is the common name of the following compound?

What is the IUPAC name of the following compound?

What is the IUPAC of the following compound?

Which of the following compounds is (are)primary alcohols?

Which of the following compounds has the highest boiling point?

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

Which of the following compounds are ethers?

Determine the product(s)of the following reaction.

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

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

Which of the following would be a reasonable synthesis of 1-butanol?

What is the major organic product of the following reaction?

What is the IUPAC of the following compound?

Determine the product(s)of the following reaction.

What is the IUPAC of the following compound?

Which of the following compounds has the highest boiling point?

What is the major alkene formed when compound A is dehydrated with POCl3 and pyridine?

What is the IUPAC of the following compound?

What is the IUPAC 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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

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 POCl₃ and pyridine?