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What is the IUPAC of the following compound? <sup> </sup>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) A) and B)
F) C) and D)

Correct Answer

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B

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


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

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

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


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

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

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

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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) None of the above

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

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

Correct Answer

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

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

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 C)
F) A) and D)

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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 B)
F) None of the above

Correct Answer

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

Correct Answer

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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) A) and D)

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 B)
F) B) and D)

Correct Answer

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A

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

Correct Answer

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Which of the following compounds is (are) primary alcohols? <sup> </sup>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) None of the above
F) All 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) All of the above
F) A) and D)

Correct Answer

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B

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 C)
F) A) and C)

Correct Answer

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What is the major alkene formed when compound A is dehydrated with H2SO4? What is the major alkene formed when compound A is dehydrated with H<sub>2</sub>SO<sub>4</sub>? A) I B) II C) III D) IV


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

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

Correct Answer

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