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What is the IUPAC name for the following compound? What is the IUPAC name for the following compound?   A) 4-Ethyl-3-methyl-1-octen-5-ol B) 3-Ethyl-4-methyl-2-octen-5-ol C) 5-Ethyl-6-methyl-7-octen-4-ol D) 4-Ethyl-6-methyl-1-octen-5-ol


A) 4-Ethyl-3-methyl-1-octen-5-ol
B) 3-Ethyl-4-methyl-2-octen-5-ol
C) 5-Ethyl-6-methyl-7-octen-4-ol
D) 4-Ethyl-6-methyl-1-octen-5-ol

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

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In which of the following alkene addition reactions will carbocation rearrangements occur?


A) Addition of Br2 and H2O
B) Addition of Br2
C) Addition of Cl2 and H2O
D) Addition of H2O in the presence of H2SO4

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

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Rank the following compounds in order of decreasing stability, putting the most stable first. Rank the following compounds in order of decreasing stability, putting the most stable first.   A) I > II > III B) II > I > III C) III > II > I D) III > I > II


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

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

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What is the IUPAC name for the following compound? What is the IUPAC name for the following compound?   A) 1-Methylcyclopentene B) 2-Methyl-1-cyclopentene C) 1-Methylene-1-methylcyclopentane D) 1-Methylcyclohexene


A) 1-Methylcyclopentene
B) 2-Methyl-1-cyclopentene
C) 1-Methylene-1-methylcyclopentane
D) 1-Methylcyclohexene

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

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Which of the following statements about hydroboration/oxidation of alkenes is true?


A) In hydroboration, the boron atom bonds to the more substituted carbon.
B) Hydroboration occurs with anti addition.
C) Oxidation occurs with retention of configuration.
D) 9-BBN does not undergo hydroboration in the same manner as BH3.

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

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What is (are) the major product(s) obtained from the following reaction? What is (are)  the major product(s)  obtained from 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 B)
F) B) and C)

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Which of the statements about the properties of the carbon-carbon double bond is not true?


A) There is restricted rotation around the carbon-carbon double bond.
B) Whenever the two groups on each end of a carbon-carbon double bond are the same, two diastereomers are possible.
C) Trans alkenes are generally more stable than cis alkenes.
D) The stability of the carbon-carbon double bond increases as the number of substituent groups increases.

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

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Rearrangements can occur in which of the following reactions?


A) Addition of Cl2 to an alkene.
B) Addition of HOBr to an alkene.
C) Addition of H2O/H3O+ to an alkene.
D) None of these.

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

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What is (are) the major product(s) obtained from the following reaction? What is (are)  the major product(s)  obtained from 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 B)

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Markovnikov addition of HBr to CH3CH=CH2 involves which of the following?


A) Initial attack by bromide anion (Br-) .
B) Initial attack by bromine radical (Br•) .
C) Formation of a primary carbocation.
D) Formation of a secondary carbocation.

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

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Which of the following reaction conditions would result in anti-Markovnikov addition to an alkene?


A) H2O/H3O+
B) HBr
C) HCl
D) [1] BH3; [2] H2O2/HO-

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

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What is the starting material in the following reaction? What is the starting material in the following reaction?   A) I B) II C) III D) IV


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

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

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What is the common name of the following compound? What is the common name of the following compound?   A) 2-Vinylcyclohexene B) 2-Allylcyclohexene C) 1-Allylcyclohexene D) 1-Vinylcyclohexene


A) 2-Vinylcyclohexene
B) 2-Allylcyclohexene
C) 1-Allylcyclohexene
D) 1-Vinylcyclohexene

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

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What type of reactive intermediate is formed in the reaction of an alkene with HI to give an iodoalkane?


A) Carbanion
B) Carbocation
C) Cyclic bromonium ion
D) Radical

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

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Which of the following alkenes is an E alkene? Which of the following alkenes is an E alkene?   A) I B) II C) III D) IV


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

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

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Which of the following statements about alkenes is true?


A) Alkenes react with nucleophiles and bases.
B) Alkenes contain double bonds from two sp-hybridized carbon atoms.
C) In the reactions of alkenes, the Which of the following statements about alkenes is true? A) Alkenes react with nucleophiles and bases. B) Alkenes contain double bonds from two sp-hybridized carbon atoms. C) In the reactions of alkenes, the  always broken. D) Alkenes react with electrophiles.always broken.
D) Alkenes react with electrophiles.

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

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Predict the major product of the following reaction. Predict the major 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) All of the above

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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) HBr B) Br<sub>2</sub>, H<sub>2</sub>O C) Br<sub>2</sub> D) H<sub>2</sub>O<sub>2</sub>/Br<sub>2</sub>


A) HBr
B) Br2, H2O
C) Br2
D) H2O2/Br2

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

Correct Answer

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Rank the carbocation in order of increasing stability, putting the least stable first. Rank the carbocation in order of increasing stability, putting the least stable first.   A) III < I < II B) III < II < I C) I < II < III D) I < III < II


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

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

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Calculate the degree of unsaturation for a molecule with molecular formula C8H9N.


A) 2
B) 3
C) 4
D) 5

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

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