Question 1

What is the common name of the following compound?

Accepted Answer

A) Methyl vinyl ether 
B) Allyl methyl ether 
C) Propenyl methyl ether 
D) Methylene propylene ether 
A) Methyl vinyl ether 
B) Allyl methyl ether 
C) Propenyl methyl ether 
D) Methylene propylene ether

Question 2

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 3

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 4

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 5

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 6

What is the IUPAC name of the following compound?

Accepted Answer

A) R-2,2-dimethylcyclohexanol 
B) S-2,2-dimethylcyclohexanol 
C) R-1,1-dimethyl-2-cyclohexanol 
D) S-1,1-dimethyl-2-cyclohexanol 
A) R-2,2-dimethylcyclohexanol 
B) S-2,2-dimethylcyclohexanol 
C) R-1,1-dimethyl-2-cyclohexanol 
D) S-1,1-dimethyl-2-cyclohexanol

Question 7

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 8

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 9

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 10

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 11

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 12

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 13

What are the major products obtained upon treatment of methyl phenyl ether with excess HBr?

Accepted Answer

A) Phenol and bromomethane 
B) Phenol and methanol 
C) Bromobenzene and bromomethane 
D) Bromobenzene and methanol 
A) Phenol and bromomethane 
B) Phenol and methanol 
C) Bromobenzene and bromomethane 
D) Bromobenzene and methanol

Question 14

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 15

What are the major products obtained upon treatment of ethyl methyl ether with excess HBr?

Accepted Answer

A) Bromomethane and ethanol 
B) Bromoethane and methanol 
C) Bromoethane and bromomethane 
D) Ethanol and methanol 
A) Bromomethane and ethanol 
B) Bromoethane and methanol 
C) Bromoethane and bromomethane 
D) Ethanol and methanol

Question 16

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 17

What is the IUPAC of the following compound?

Accepted Answer

A) 1,1-Dimethyloxirane 
B) 2-Methylpropylane 
C) 2-Methylpropylene oxide 
D) 2,2-Dimethyloxirane 
A) 1,1-Dimethyloxirane 
B) 2-Methylpropylane 
C) 2-Methylpropylene oxide 
D) 2,2-Dimethyloxirane

Question 18

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 19

What are the major products obtained upon treatment of tert-butyl methyl ether with excess HI?

Accepted Answer

A) tert-Butyl alcohol and iodomethane 
B) tert-Butyl iodide and iodomethane 
C) tert-Butyl alcohol and methanol 
D) tert-Butyl iodide and methanol 
A) tert-Butyl alcohol and iodomethane 
B) tert-Butyl iodide and iodomethane 
C) tert-Butyl alcohol and methanol 
D) tert-Butyl iodide and methanol

Question 20

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

Accepted Answer

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

Exam 9: Alcohols,ethers,and Related Compounds

What is the common name of the following compound?

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

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

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

Determine the product(s)of the following reaction.

What is the IUPAC name of the following compound?

What is the IUPAC of the following compound?

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

Determine the product(s)of the following reaction.

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

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

What is the major product of the following reaction?

What are the major products obtained upon treatment of methyl phenyl ether with excess HBr?

What is the IUPAC of the following compound?

What are the major products obtained upon treatment of ethyl methyl ether with excess HBr?

What is the product of the following reaction?

What is the IUPAC of the following compound?

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

What are the major products obtained upon treatment of tert-butyl methyl ether with excess HI?

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

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

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