Question 1

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 2

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 3

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

Question 4

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

Question 5

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 6

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 7

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 8

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 9

Which of the following explains why epoxides are much more reactive than ethers?

Accepted Answer

A) The C-O-C bond angle of an epoxide is 109°,making epoxides to have angle strain. 
B) The oxygen atom of an epoxide is sp2 hybridized. 
C) The C-O-C bond angle of an epoxide is 120°,making epoxides to have angle strain. 
D) The C-O-C bond angle of an epoxide is 60°,making epoxides to have angle strain. 
A) The C-O-C bond angle of an epoxide is 109°,making epoxides to have angle strain. 
B) The oxygen atom of an epoxide is sp2 hybridized. 
C) The C-O-C bond angle of an epoxide is 120°,making epoxides to have angle strain. 
D) The C-O-C bond angle of an epoxide is 60°,making epoxides to have angle strain.

Question 10

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 11

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 12

What is the IUPAC of the following compound? (CH3CH2)3COH

Accepted Answer

A) 2-Ethyl-2-pentanol 
B) 2-Ethyl-3-pentanol 
C) 3-Ethyl-3-pentanol 
D) 2,2-Diethyl-1-butanol 
A) 2-Ethyl-2-pentanol 
B) 2-Ethyl-3-pentanol 
C) 3-Ethyl-3-pentanol 
D) 2,2-Diethyl-1-butanol

Question 13

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 14

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 15

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

Question 16

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 17

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

Accepted Answer

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

Question 18

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 19

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 20

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

Exam 9: Alcohols,ethers,and Related Compounds

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

What is the IUPAC of the following compound?

What is the IUPAC name of the following compound?

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

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

What is the major organic product of the following reaction?

What is the IUPAC of the following compound?

What is the product of the following reaction?

Which of the following explains why epoxides are much more reactive than ethers?

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

What is the IUPAC of the following compound?

What is the IUPAC of the following compound? (CH3CH2)3COH

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

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

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

Which of the following compounds has the highest boiling point?

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

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

What is the major organic product of the following reaction?

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

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 IUPAC of the following compound? (CH₃CH₂)₃COH