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Predict the major product of the following reaction. Predict the major product of the following reaction. A) B) C) D)


A)
Predict the major product of the following reaction. A) B) C) D)
B)
Predict the major product of the following reaction. A) B) C) D)
C)
Predict the major product of the following reaction. A) B) C) D)
D)
Predict the major product of the following reaction. A) B) C) D)

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

Correct Answer

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Which of the following carbocations is(are) likely to undergo a rearrangement? Which of the following carbocations is(are) likely to undergo a rearrangement? A) only I B) I and III C) II and III D) I, II, and III


A) only I
B) I and III
C) II and III
D) I, II, and III

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

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Which of the following alkenes exhibit E-Z isomerism? I. CH3CH2CH=CHCH2CH3\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{CH}_{3} II. (CH3) 2C=CHCH3\left(\mathrm{CH}_{3}\right) _{2} \mathrm{C}=\mathrm{CHCH}_{3} III. CH3CH2CH=CHBr\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CHBr} IV. H2C=CHCH2CH(CH3) 2\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) _{2}


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

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

Correct Answer

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Identify the major organic product expected from the acid-catalyzed dehydration of 2-methyl-2pentanol.


A) 2-methyl-1-pentene
B) 2-methyl-2-pentene
C) 3-methyl-1-pentene
D) cis-3-methyl-2-pentene

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

Correct Answer

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Which of the following would have the fastest rate of reaction to form 4-tert-butylcyclohexene?


A)
Which of the following would have the fastest rate of reaction to form 4-tert-butylcyclohexene? A) B) C) D)
B)
Which of the following would have the fastest rate of reaction to form 4-tert-butylcyclohexene? A) B) C) D)
C)
Which of the following would have the fastest rate of reaction to form 4-tert-butylcyclohexene? A) B) C) D)
D)
Which of the following would have the fastest rate of reaction to form 4-tert-butylcyclohexene? A) B) C) D)

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

Correct Answer

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Which of the following cannot undergo an E2 reaction? Which of the following cannot undergo an E2 reaction? A) only I B) only II C) only III D) I and III


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

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

Correct Answer

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A

What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-methyl-2-propanol? What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-methyl-2-propanol? A) Protonation of the alcohol to form an oxonium ion. B) Loss of water from the oxonium ion to form a carbocation. C) Loss of a \beta -hydrogen from the carbocation to form an alkene. D) The simultaneous loss of a \beta -hydrogen and water from the oxonium ion.


A) Protonation of the alcohol to form an oxonium ion.
B) Loss of water from the oxonium ion to form a carbocation.
C) Loss of a β\beta -hydrogen from the carbocation to form an alkene.
D) The simultaneous loss of a β\beta -hydrogen and water from the oxonium ion.

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

Correct Answer

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Which of the following stereoisomers gives the exclusive E2 product shown? Which of the following stereoisomers gives the exclusive E2 product shown? A) B) C) D)


A)
Which of the following stereoisomers gives the exclusive E2 product shown? A) B) C) D)
B)
Which of the following stereoisomers gives the exclusive E2 product shown? A) B) C) D)
C)
Which of the following stereoisomers gives the exclusive E2 product shown? A) B) C) D)
D)
Which of the following stereoisomers gives the exclusive E2 product shown? A) B) C) D)

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

Correct Answer

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Which of the alkenes below has the Z-configuration?


A)
Which of the alkenes below has the Z-configuration? A) B) C) D)
B)
Which of the alkenes below has the Z-configuration? A) B) C) D)
C)
Which of the alkenes below has the Z-configuration? A) B) C) D)
D)
Which of the alkenes below has the Z-configuration? A) B) C) D)

E) B) and C)
F) A) 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) 2-methyl-3-propyl-2-pentene B) 3-ethyl-2-methyl-2-hexene C) 4-ethyl-5-methyl-4-hexene D) 4-methyl-3-propyl-3-pentene


A) 2-methyl-3-propyl-2-pentene
B) 3-ethyl-2-methyl-2-hexene
C) 4-ethyl-5-methyl-4-hexene
D) 4-methyl-3-propyl-3-pentene

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

Correct Answer

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In the dehydrohalogenation of 2-bromobutane, which conformation below leads directly to the formation of cis-2-butene? In the dehydrohalogenation of 2-bromobutane, which conformation below leads directly to the formation of cis-2-butene? A) only I B) only II C) only III D) I and II


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

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

Correct Answer

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A

Which of the following C6H12\mathrm{C}_{6} \mathrm{H}_{12} isomers has the highest heat of combustion?


A) 1-hexene
B) trans-3-hexene
C) cis-3-hexene
D) 2-methyl-2-pentene

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

Correct Answer

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Which of the following does not give 1, 2-dimethylcyclohexene as one of the acid-catalyzed dehydration products?


A) Which of the following does not give 1, 2-dimethylcyclohexene as one of the acid-catalyzed dehydration products? A) B) C) D)
B) Which of the following does not give 1, 2-dimethylcyclohexene as one of the acid-catalyzed dehydration products? A) B) C) D)
C) Which of the following does not give 1, 2-dimethylcyclohexene as one of the acid-catalyzed dehydration products? A) B) C) D)
D) Which of the following does not give 1, 2-dimethylcyclohexene as one of the acid-catalyzed dehydration products? A) B) C) D)

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

Correct Answer

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D

Which of the following compounds gives a single E2 product on reaction with sodium ethoxide, NaOCH2CH3\mathrm{NaOCH}_{2} \mathrm{CH}_{3} ? Which of the following compounds gives a single E2 product on reaction with sodium ethoxide, \mathrm{NaOCH}_{2} \mathrm{CH}_{3} ? A) I and II B) I and III C) II and III D) I, II, and III


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

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

Correct Answer

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If you wanted to make compound III, starting with compound I or II, what would you do? If you wanted to make compound III, starting with compound I or II, what would you do? A) React I with \mathrm{H}_{2} \mathrm{SO}_{4} . B) React II with NaOEt. C) Either of the reactions in A or B above would work. D) Neither of the reactions in A or B above would work.


A) React I with H2SO4\mathrm{H}_{2} \mathrm{SO}_{4} .
B) React II with NaOEt.
C) Either of the reactions in A or B above would work.
D) Neither of the reactions in A or B above would work.

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

Correct Answer

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What is the first step in the mechanism of the dehydration reaction of a tertiary alcohol with sulfuric acid to form an alkene?


A) the loss of OH−\mathrm{OH}^{-} to form a carbocation
B) the protonation of the hydroxyl group
C) the loss of the proton from the hydroxyl group to give an alkoxide ion
D) the removal of a β\beta -hydrogen from the alcohol

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

Correct Answer

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Carbon-carbon double bonds do not freely rotate like carbon-carbon single bonds. Why?


A) The double bond is much stronger and thus more difficult to rotate.
B) Overlap of the two 2 p orbitals of the π\pi bond would be lost.
C) The shorter bond length of the double bond makes it more difficult for the attached groups to pass each other.
D) Overlap of the sp2\mathrm{sp}^{2} orbitals of the carbon-carbon σ\sigma bond would be lost.

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

Correct Answer

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What is the major product of the reaction sequence shown below? What is the major product of the reaction sequence shown below? A) 2-methyl-1-butene B) 2-methyl-2-butene C) 3-methyl-1-butene D) 2-methylbutane


A) 2-methyl-1-butene
B) 2-methyl-2-butene
C) 3-methyl-1-butene
D) 2-methylbutane

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

Correct Answer

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Showing 1 - 18 of 18

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