Question 1

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. D

Question 2

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

Accepted Answer

A) HCl 
B) SOCl2,pyridine 
C) Cl2 
D) H3O+,H2O 
A) HCl 
B) SOCl2,pyridine 
C) Cl2 
D) H3O+,H2O B

Question 3

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 B

Question 4

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 5

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 6

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

Accepted Answer

A) 2-Methyl-1-butene 
B) 3-Methyl-3-butene 
C) 1-Chloro-2-methylbutane 
D) 1-Bromo-2-methylbutane 
A) 2-Methyl-1-butene 
B) 3-Methyl-3-butene 
C) 1-Chloro-2-methylbutane 
D) 1-Bromo-2-methylbutane

Question 7

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 8

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

Question 9

What is the IUPAC of the following compound?

Accepted Answer

A) (S)-2,2-Dimethyl-3-pentanol 
B) (R)-2,2-Dimethyl-3-pentanol 
C) (R)-4,4-Dimethyl-3-pentanol 
D) (S)-1-tert-Butyl-1-propanol 
A) (S)-2,2-Dimethyl-3-pentanol 
B) (R)-2,2-Dimethyl-3-pentanol 
C) (R)-4,4-Dimethyl-3-pentanol 
D) (S)-1-tert-Butyl-1-propanol

Question 10

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

Question 11

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 12

Which of the following alcohols reacts the fastest with HCl to give the corresponding alkyl halide?

Accepted Answer

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

Question 13

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 14

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 15

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 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 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 18

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 19

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 20

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.

Exam 9: Alcohols,ethers,and Related Compounds

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

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

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

What is the common name of the following compound?

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

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

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

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

What is the IUPAC of the following compound?

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

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

Which of the following alcohols reacts the fastest with HCl to give the corresponding alkyl halide?

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

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

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

What is the product of the following reaction?

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?

What is the product of the following reaction?

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

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

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