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


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

E) A) and C)
F) A) and D)

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What is the product of the following reaction? What is the product of the following reaction? A) I B) II C) III D) IV


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

E) All of the above
F) A) and D)

Correct Answer

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What is the IUPAC of the following compound? What is the IUPAC of the following compound? 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

E) All of the above
F) A) and C)

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Determine the product(s) of the following reaction. Determine the product(s) of the following reaction. 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

E) B) and C)
F) All of the above

Correct Answer

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D

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


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

E) C) and D)
F) None of the above

Correct Answer

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What is the best choice of reagent to accomplish the following transformation? What is the best choice of reagent to accomplish the following transformation? A) HCl B) SOCl<sub>2</sub>, pyridine C) Cl<sub>2</sub> D) H<sub>3</sub>O<sup>+</sup>, H<sub>2</sub>O


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

E) A) and B)
F) All of the above

Correct Answer

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What is the IUPAC of the following compound? What is the IUPAC of the following compound? 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

E) None of the above
F) B) and D)

Correct Answer

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Which of the following would be a reasonable synthesis of 2-butanol? Which of the following would be a reasonable synthesis of 2-butanol? A) I B) II C) III D) IV


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

E) B) and C)
F) C) and D)

Correct Answer

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A

What is the major organic product(s) obtained in the following reaction? What is the major organic product(s) obtained in the following reaction? A) I B) II C) III D) I and II


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

E) All of the above
F) A) and B)

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Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements? Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements? A) I B) II C) III D) IV


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

E) B) and C)
F) None of the above

Correct Answer

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What is the IUPAC of the following compound? What is the IUPAC of the following compound? 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

E) A) and D)
F) B) and C)

Correct Answer

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B

Which of the following compounds has the highest boiling point? Which of the following compounds has the highest boiling point? A) I B) II C) III D) IV


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

E) A) and D)
F) B) and D)

Correct Answer

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


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

E) None of the above
F) A) and B)

Correct Answer

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What is the IUPAC of the following compound? What is the IUPAC of the following compound? 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

E) B) and D)
F) A) and D)

Correct Answer

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Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4, putting the least reactive first. Rank the alcohols in order of increasing reactivity when dehydrated with H<sub>2</sub>SO<sub>4</sub>, putting the least reactive first. 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

E) B) and C)
F) A) and D)

Correct Answer

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Which of the following would be a reasonable synthesis of 1-butanol? Which of the following would be a reasonable synthesis of 1-butanol? A) I B) II C) III D) IV


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

E) B) and D)
F) A) and C)

Correct Answer

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

E) B) and C)
F) All of the above

Correct Answer

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

E) All of the above
F) A) and B)

Correct Answer

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Determine the product in the following reaction (ignoring possible stereoisomers) . Determine the product in the following reaction (ignoring possible stereoisomers) . A) I B) II C) III D) IV


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

E) A) and B)
F) B) and D)

Correct Answer

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


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.

E) None of the above
F) B) and C)

Correct Answer

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