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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 B)
F) B) and C)

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

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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) B) and C)

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


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

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

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

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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) None of the above
F) All of the above

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

Correct Answer

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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 D)

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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) None of the above
F) All of the above

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

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What is the major alkene formed when compound A is dehydrated with POCl3 and pyridine? What is the major alkene formed when compound A is dehydrated with POCl<sub>3</sub> and pyridine? A) I B) II C) III D) IV


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

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

Correct Answer

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Which of the following compounds is (are) secondary alcohols? Which of the following compounds is (are) secondary alcohols? A) Only I B) Only II C) Only II and III D) Only III and IV


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

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

Correct Answer

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


A) Bromomethane and ethanol
B) Bromoethane and methanol
C) Bromoethane and bromomethane
D) Ethanol and methanol

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

Correct Answer

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) R-2,2-dimethylcyclohexanol B) S-2,2-dimethylcyclohexanol C) R-1,1-dimethyl-2-cyclohexanol D) S-1,1-dimethyl-2-cyclohexanol


A) R-2,2-dimethylcyclohexanol
B) S-2,2-dimethylcyclohexanol
C) R-1,1-dimethyl-2-cyclohexanol
D) S-1,1-dimethyl-2-cyclohexanol

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

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 vinyl ether B) Allyl methyl ether C) Propenyl methyl ether D) Methylene propylene ether


A) Methyl vinyl ether
B) Allyl methyl ether
C) Propenyl methyl ether
D) Methylene propylene ether

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

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

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

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 II and III


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

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

Correct Answer

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