Question 1

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 2

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 B

Question 3

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 A

Question 4

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 5

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 6

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 7

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 8

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 9

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 10

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 11

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 12

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 13

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 14

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 15

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 16

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 17

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 18

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 19

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 20

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Exam 9: Alcohols, Ethers, and Related Compounds

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

What is the IUPAC of the following compound?

What is the product of the following reaction?

Determine the product(s) of the following reaction.

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

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

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

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

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

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

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

What is the major organic product of the following reaction?

What is the IUPAC of the following compound?

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

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

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

What is the major organic 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 is the major organic product obtained from the following reaction?

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

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

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

Synthetic Polymers

Lipids

Filters

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