Question 1

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 B

Question 2

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 A

Question 3

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 D

Question 4

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 5

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 6

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 7

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 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 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 10

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 11

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 12

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 13

Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4, putting the least reactive first.

Accepted Answer

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

Question 14

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 15

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 16

What is the major organic product(s) obtained in the following reaction?

Accepted Answer

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

Question 17

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 18

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.

Question 19

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 20

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

Exam 9: Alcohols, Ethers and Epoxides

What is the IUPAC of the following compound?

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

Determine the product(s) of the following reaction.

Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements?

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

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

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

What is the product of the following reaction?

Which of the following compounds has the highest boiling point?

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

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

What is the IUPAC of the following compound?

Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4, putting the least reactive first.

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

What is the IUPAC of the following compound?

What is the major organic product(s) obtained in the following reaction?

What is the IUPAC of the following compound?

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

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?

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

Filters

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

Rank the alcohols in order of increasing reactivity when dehydrated with H₂SO₄, putting the least reactive first.