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Draw the mechanism for the following dehydration. Draw the mechanism for the following dehydration.

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Which of the following is the correct structure of 4-methylcyclopentene?


A) Which of the following is the correct structure of 4-methylcyclopentene? A) B) C) D)
B) Which of the following is the correct structure of 4-methylcyclopentene? A) B) C) D)
C) Which of the following is the correct structure of 4-methylcyclopentene? A) B) C) D)
D) Which of the following is the correct structure of 4-methylcyclopentene? A) B) C) D)

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Draw the mechanism and product for the following elimination, without using rearrangement. Draw the mechanism and product for the following elimination, without using rearrangement.

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Which of the following is the correct structure of 2-methyl-1-butene?


A) Which of the following is the correct structure of 2-methyl-1-butene? A) B) C) D)
B) Which of the following is the correct structure of 2-methyl-1-butene? A) B) C) D)
C) Which of the following is the correct structure of 2-methyl-1-butene? A) B) C) D)
D) Which of the following is the correct structure of 2-methyl-1-butene? A) B) C) D)

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What is (are) the most likely product(s) for the following reaction? What is (are) the most likely product(s) for the following reaction?

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How would you change the following reaction conditions to favor an E2 mechanism? How would you change the following reaction conditions to favor an E2 mechanism?

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How many distinct signals would appear in the (proton-decoupled) 13C NMR spectrum for the following compound? How many distinct signals would appear in the (proton-decoupled) <sup>13</sup>C NMR spectrum for the following compound? A) 4 B) 5 C) 6 D) 8


A) 4
B) 5
C) 6
D) 8

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Which of the following is the strongest nucleophile?


A) Which of the following is the strongest nucleophile? A) B) C) D)
B) Which of the following is the strongest nucleophile? A) B) C) D)
C) Which of the following is the strongest nucleophile? A) B) C) D)
D) Which of the following is the strongest nucleophile? A) B) C) D)

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Which of the following is most reactive in an E1 reaction?


A) Which of the following is most reactive in an E1 reaction? A) B) C)
B) Which of the following is most reactive in an E1 reaction? A) B) C)
C) Which of the following is most reactive in an E1 reaction? A) B) C)

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Which of the following alkyl halides would be more reactive in an E2 elimination?


A) Which of the following alkyl halides would be more reactive in an E2 elimination? A) B)
B) Which of the following alkyl halides would be more reactive in an E2 elimination? A) B)

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Draw the major product of the following elimination. Draw the major product of the following elimination.

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What is the structure of a rearranged carbocation that does not have a four-membered ring in the following acid-catalyzed dehydration of the following compound? What is the structure of a rearranged carbocation that does not have a four-membered ring in the following acid-catalyzed dehydration of the following compound?

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For the following dehydration, draw the structure of the intermediate carbocation. For the following dehydration, draw the structure of the intermediate carbocation.

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Draw the major product of the following reaction. Draw the major product of the following reaction.

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By what mechanism is the following reaction likely to occur? By what mechanism is the following reaction likely to occur?

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What is the degree of substitution of the following alkene? What is the degree of substitution of the following alkene? A) Monosubstituted B) Disubstituted C) Trisubstituted D) Tetrasubstituted


A) Monosubstituted
B) Disubstituted
C) Trisubstituted
D) Tetrasubstituted

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What is the product of the following elimination? What is the product of the following elimination?

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Which of the following is the IUPAC name for the following compound? Which of the following is the IUPAC name for the following compound? A) 2-ethyl-1,1,3-trimethylbutene B) 3-ethyl-2,4-dimethyl-2-pentene C) 2,4-dimethylhexene D) 4-ethyl-1,3-dimethyl-3-pentene


A) 2-ethyl-1,1,3-trimethylbutene
B) 3-ethyl-2,4-dimethyl-2-pentene
C) 2,4-dimethylhexene
D) 4-ethyl-1,3-dimethyl-3-pentene

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Draw the major product of the following reaction. Draw the major product of the following reaction.

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Which of the following is the correct mechanism for the elimination reaction of 2-bromo-2,3-dimethylbutane with methoxide?


A) Which of the following is the correct mechanism for the elimination reaction of 2-bromo-2,3-dimethylbutane with methoxide? A) B) C) D)
B) Which of the following is the correct mechanism for the elimination reaction of 2-bromo-2,3-dimethylbutane with methoxide? A) B) C) D)
C) Which of the following is the correct mechanism for the elimination reaction of 2-bromo-2,3-dimethylbutane with methoxide? A) B) C) D)
D) Which of the following is the correct mechanism for the elimination reaction of 2-bromo-2,3-dimethylbutane with methoxide? A) B) C) D)

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