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Which of the following ethers cannot be prepared by the Williamson ether synthesis?


A) Isopropyl methyl ether
B) tert-Butyl methyl ether
C) tert-Butyl phenyl ether
D) Methyl phenyl ether

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

Correct Answer

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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) C) and D)
F) All of the above

Correct Answer

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

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

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What is the IUPAC of the following compound? What is the IUPAC of the following compound? A) 5-Hydroxy-3-methyl-1-pentene B) 3-Methyl-5-penten-1-ol C) 3-Methyl-1-penten-5-ol D) 3-Methyl-4-penten-1-ol


A) 5-Hydroxy-3-methyl-1-pentene
B) 3-Methyl-5-penten-1-ol
C) 3-Methyl-1-penten-5-ol
D) 3-Methyl-4-penten-1-ol

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

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


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.

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

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


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.

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

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Which of the following compounds are ethers? Which of the following compounds are ethers? A) Only I and II B) Only III and IV C) Only I, II and III D) I, II, III and IV


A) Only I and II
B) Only III and IV
C) Only I, II and III
D) I, II, III and IV

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

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-4-methylcyclohexane B) 3,4-Epoxy-1-methylcyclohexane C) 1,2-Epoxy-3-methylcyclohexane D) 1,2-Epoxy-5-methylcyclohexane


A) 1,2-Epoxy-4-methylcyclohexane
B) 3,4-Epoxy-1-methylcyclohexane
C) 1,2-Epoxy-3-methylcyclohexane
D) 1,2-Epoxy-5-methylcyclohexane

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

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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 D)
F) C) 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) Ethoxyoctane B) 5-Ethoxyoctane C) 4-Ethoxyoctane D) Ethyl octyl ether


A) Ethoxyoctane
B) 5-Ethoxyoctane
C) 4-Ethoxyoctane
D) Ethyl octyl ether

E) A) and C)
F) A) 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) Bromobenzene and sodium methoxide.
B) Phenol and sodium methoxide.
C) Bromobenzene and bromomethane.
D) Sodium phenoxide and bromomethane.

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

Correct Answer

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What is the common name of the following compound? What is the common name of the following compound? A) Methyl sec-butyl ether B) Isobutyl methyl ether C) sec-Butyl methyl ether D) Butyl methyl ether


A) Methyl sec-butyl ether
B) Isobutyl methyl ether
C) sec-Butyl methyl ether
D) Butyl methyl ether

E) A) 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) TsCl, pyridine B) POCl<sub>3</sub>, pyridine C) HCl, ZnCl<sub>2</sub> D) NaOH


A) TsCl, pyridine
B) POCl3, pyridine
C) HCl, ZnCl2
D) NaOH

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

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) (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

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

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


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

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

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) H<sub>2</sub>SO<sub>4</sub> C) NaOH D) TsCl, pyridine


A) HCl
B) H2SO4
C) NaOH
D) TsCl, pyridine

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

Correct Answer

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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 I and II


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

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

Correct Answer

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


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.

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

Correct Answer

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Which of the following compounds is (are) symmetrical ethers? Which of the following compounds is (are) symmetrical ethers? A) Only I B) Only IV C) Only III and IV D) Only I, III and IV


A) Only I
B) Only IV
C) Only III and IV
D) Only I, III and IV

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

Correct Answer

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

Correct Answer

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