Question 1

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

Question 2

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

Question 3

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

Accepted Answer

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

Question 4

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 5

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 6

Which of the following statements about the reaction of ethers with strong acids is true?

Accepted Answer

A)  HCl, HBr and HI can all be used. 
B)  The mechanism of ether cleavage is SN1 only. 
C)  The mechanism of ether cleavage is SN2 only. 
D)  The mechanism of ether cleavage is SN1 and SN2. 
A)  HCl, HBr and HI can all be used. 
B)  The mechanism of ether cleavage is SN1 only. 
C)  The mechanism of ether cleavage is SN2 only. 
D)  The mechanism of ether cleavage is SN1 and SN2.

Question 7

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 8

What is the best choice of reagent to accomplish the following transformation?

Accepted Answer

A)  TsCl, pyridine 
B)  POCl3, pyridine 
C)  HCl, ZnCl2 
D)  NaOH 
A)  TsCl, pyridine 
B)  POCl3, pyridine 
C)  HCl, ZnCl2 
D)  NaOH

Question 9

Which of the following ethers cannot be prepared by the Williamson ether synthesis?

Accepted Answer

A)  Isopropyl methyl ether 
B)  tert-Butyl methyl ether 
C)  tert-Butyl phenyl ether 
D)  Methyl phenyl ether 
A)  Isopropyl methyl ether 
B)  tert-Butyl methyl ether 
C)  tert-Butyl phenyl ether 
D)  Methyl phenyl ether

Question 10

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 11

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 12

What is the IUPAC of the following compound?

Accepted Answer

A)  5-Hydroxy-3-methyl-1-pentene 
B)  3-Methyl-5-penten-1-ol 
C)  3-Methyl-1-penten-5-ol 
D)  3-Methyl-4-penten-1-ol 
A)  5-Hydroxy-3-methyl-1-pentene 
B)  3-Methyl-5-penten-1-ol 
C)  3-Methyl-1-penten-5-ol 
D)  3-Methyl-4-penten-1-ol

Question 13

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.

Question 14

Which of the following statements about carbocation rearrangement is not true?

Accepted Answer

A)  A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom. 
B)  A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group. 
C)  1,2-Shifts convert a less stable carbocation to a more stable carbocation. 
D)  The migrating group in a 1,2-shift moves with one bonding electron. 
A)  A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom. 
B)  A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group. 
C)  1,2-Shifts convert a less stable carbocation to a more stable carbocation. 
D)  The migrating group in a 1,2-shift moves with one bonding electron.

Question 15

What is the product of the following reaction?

Accepted Answer

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

Question 16

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 17

What is the best choice of reagent to accomplish the following transformation?

Accepted Answer

A)  HCl 
B)  H2SO4 
C)  NaOH 
D)  TsCl, pyridine 
A)  HCl 
B)  H2SO4 
C)  NaOH 
D)  TsCl, pyridine

Question 18

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 19

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 20

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

Exam 9: Alcohols, Ethers and Epoxides

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

What is the common name of the following compound?

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

What is the IUPAC of the following compound?

Which of the following compounds has the highest boiling point?

Which of the following statements about the reaction of ethers with strong acids is true?

Which of the following compounds are ethers?

What is the best choice of reagent to accomplish the following transformation?

Which of the following ethers cannot be prepared by the Williamson ether synthesis?

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

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

What is the IUPAC of the following compound?

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

Which of the following statements about carbocation rearrangement is not true?

What is the product of the following reaction?

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

What is the best choice of reagent to accomplish the following transformation?

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

Determine the product(s) of the following reaction.

What is the IUPAC 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

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

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

Lipids

Synthetic Polymers

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