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Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with H2/Pd? Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with H<sub>2</sub>/Pd?   A)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

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

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What is the major product obtained upon addition of Br2 to (R) -4-tert-butylcyclohexene?


A) (1R,2R,4R) -1,2-dibromo-4-tert-butylcyclohexane
B) (1S,2R,4R) -1,2-dibromo-4-tert-butylcyclohexane
C) (1S,2S,4R) -1,2-dibromo-4-tert-butylcyclohexane
D) (1S,2S,4S) -1,2-dibromo-4-tert-butylcyclohexane

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

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What is the best choice of reagent(s) to perform the following transformation? What is the best choice of reagent(s)  to perform the following transformation?   A)  H<sub>2</sub>O, H<sub>2</sub>SO<sub>4</sub> B)  Hg(OAc) <sub>2</sub> and H<sub>2</sub>O; followed by NaBH<sub>4</sub> C)  BH<sub>3</sub>; followed by H<sub>2</sub>O<sub>2</sub>, NaOH D)  OsO<sub>4</sub>; followed by NaHSO<sub>3</sub>


A) H2O, H2SO4
B) Hg(OAc) 2 and H2O; followed by NaBH4
C) BH3; followed by H2O2, NaOH
D) OsO4; followed by NaHSO3

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

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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)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

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

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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?

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What is the best choice of reagent(s) to perform the following transformation? What is the best choice of reagent(s)  to perform the following transformation?   A)  O<sub>3</sub>; followed by (CH<sub>3</sub>) <sub>2</sub>S B)  Hg(OAc) <sub>2</sub> and H<sub>2</sub>O; followed by NaBH<sub>4</sub> C)  BH<sub>3</sub>; followed by H<sub>2</sub>O<sub>2</sub>, NaOH D)  OsO<sub>4</sub>; followed by NaHSO<sub>3</sub>


A) O3; followed by (CH3) 2S
B) Hg(OAc) 2 and H2O; followed by NaBH4
C) BH3; followed by H2O2, NaOH
D) OsO4; followed by NaHSO3

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

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Which of the following reactions of alkenes takes place with anti stereospecificity?


A) bishydroxylation (treatment with OsO4 followed by NaHSO3)
B) hydrogenation (treatment with H2/Pt)
C) addition of HBr (treatment with HBr)
D) bromohydrin formation (treatment with Br2, H2O)

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

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What is the best choice of reagent(s) to perform the following transformation? What is the best choice of reagent(s)  to perform the following transformation?   A)  H<sub>2</sub>O, H<sub>2</sub>SO<sub>4</sub> B)  Hg(OAc) <sub>2</sub> and H<sub>2</sub>O ; followed by NaBH<sub>4</sub> C)  B<sub>2</sub>H<sub>6</sub>; followed by H<sub>2</sub>O<sub>2</sub>, NaOH D)  OsO<sub>4</sub>; followed by NaHSO<sub>3</sub>


A) H2O, H2SO4
B) Hg(OAc) 2 and H2O ; followed by NaBH4
C) B2H6; followed by H2O2, NaOH
D) OsO4; followed by NaHSO3

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

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What is the correct order of exothermicity for hydrogenation of the following butenes upon treatment with H2/Pd (more exothermic > less exothermic) ? What is the correct order of exothermicity for hydrogenation of the following butenes upon treatment with H<sub>2</sub>/Pd (more exothermic > less exothermic) ?   A)  1 > 2 > 3 B)  1 > 3 > 2 C)  3 > 2 > 1 D)  2 > 3 > 1


A) 1 > 2 > 3
B) 1 > 3 > 2
C) 3 > 2 > 1
D) 2 > 3 > 1

E) None of the above
F) All of the above

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Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

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The reaction proceeds in three...

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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)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

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

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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)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

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

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The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction. The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction.   -Product _____ would have a higher energy transition state for the formation of the intermediate leading to it. -Product _____ would have a higher energy transition state for the formation of the intermediate leading to it.

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Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

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The reaction proceeds in three...

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The reagents that could effect the following conversion are: BH3, then H2O2 and NaOH. The reagents that could effect the following conversion are: BH<sub>3</sub>, then H<sub>2</sub>O<sub>2</sub> and NaOH.

A) True
B) False

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Which of the following reactions of alkenes is stereospecific?


A) addition of HCl (treatment with HCl)
B) hydrogenation (treatment with H2/Pt)
C) addition of HBr (treatment with HBr)
D) acid-catalyzed hydration (treatment with aqueous H2SO4)

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

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Identify the given structure given. ​ Identify the given structure given. ​   A)  Tetraphenyl phosphate B)  BINOL C)  BINAP D)  Binaphthyl


A) Tetraphenyl phosphate
B) BINOL
C) BINAP
D) Binaphthyl

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

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Which of the following reactions of alkenes is not stereospecific?


A) bromination (treatment with Br2 in CHCl3)
B) hydrogenation (treatment with H2/Pt)
C) acid-catalyzed hydration (treatment with aqueous H2SO4)
D) bromohydrin formation (treatment with Br2/H2O)

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

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_____________is the starting material required to produce 3-methyl-1-butanol using the hydroboration-oxidation reaction. (Enter an IUPAC name.)

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The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction. The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction.   -Product _____ would be formed by a carbocation experiencing the greatest degree of hyperconjugation stabilization. -Product _____ would be formed by a carbocation experiencing the greatest degree of hyperconjugation stabilization.

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