Question 1

Indicate the compound that has the shortest bond length between the two middle carbon atoms.

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Question 2

Among a series of isomeric trienes, the more negative the ΔH° of the hydrogenation reaction of a given triene, the ________ stable it is relative to the others in the isomeric series.

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Question 3

Arrange the following unsaturated hydrocarbons in order of decreasing reactivity toward HBr addition:

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Question 4

Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing ΔH° of this reaction. The most negative ΔH° should be listed first.
2,5-dimethyl-1,3-cycloheptadiene,
1,4-dimethyl-1,3-cycloheptadiene, and
3,6-dimethyl-1,4-cycloheptadiene

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Question 5

Draw the LUMO of 1,3,5-hexatriene.

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Question 6

Excluding the horizontal node which is coincident with the molecular plane, how many nodes are present in Ψ₄ of the 1, 3, 5-hexatriene π system?

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Question 7

Draw the HOMO of 1,3,5-hexatriene.

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Question 8

Identify the most stable carbocation.

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...

Question 9

In the molecular orbital representation of benzene, how many π molecular orbitals are present?

Accepted Answer

In the molecular orbital representation of benzene, there are six π molecular orbitals present. This is because benzene has six π electrons, which fill the six π molecular orbitals in order of increasing energy. The first two electrons fill the lowest energy π molecular orbital, the next two fill the second lowest energy π molecular orbital, and so on until all six electrons are distributed among the six π molecular orbitals.

Question 10

Provide a diagram which depicts the relative energies of the π molecular orbitals of benzene. Show which molecular orbitals are filled in benzene's ground state.

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Question 11

Which of the following is the weakest base?

Accepted Answer

The acetate ion is the weakest base among the options given because it has resonance stabilization when it accepts a proton, making it less likely to act as a base compared to the other options which are less stabilized or more reactive as bases.

Question 12

Which of the following ions is most acidic?

Accepted Answer

The presence of the sulfuric acid group (-SO3H) makes ion A the most acidic as it can release H+ ions more easily. The other options have weaker acid groups or lack them altogether.

Question 13

Which species is represented by the following distribution of π electrons in the molecular orbitals and energy levels diagram?

Accepted Answer

The species represented in the diagram has 10 π electrons in total. Looking at the diagram, we can see that there are two sets of degenerate orbitals. One set contains 4 π electrons and the other set contains 6 π electrons. This suggests that the species has two double bonds and one lone pair of electrons. The only option that fits this description is choice C), which represents an allyl anion.

Question 14

Which π MOs are bonding MOs in the ground state of 1,3,5-hexatriene?

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Question 15

Which of the following is/are the major product(s)of the following reaction?

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Question 16

Which of the following is the strongest acid?

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Question 17

Show how the p orbitals overlap to form the nonbonding π molecular orbital of the allyl system.

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Question 18

Which of the following is the strongest acid?

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Question 19

Identify the most stable carbocation.

Accepted Answer

Carbocations are stabilized by adjacent electron-donating groups. In choice C, there are two methyl groups adjacent to the carbocation, which can donate electrons and stabilize the positive charge. In choices A, B, D, and E, there is only one electron-donating group adjacent to the carbocation. Therefore, choice C is the most stable carbocation.

Question 20

Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing ΔH° of this reaction. The most negative ΔH° should be listed first.
cis-2-pentene, 2,3-pentadiene, and trans-1,3-pentadiene

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Quiz 8: Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Indicate the compound that has the shortest bond length between the two middle carbon atoms.

Among a series of isomeric trienes, the more negative the ΔH° of the hydrogenation reaction of a given triene, the ________ stable it is relative to the others in the isomeric series.

Arrange the following unsaturated hydrocarbons in order of decreasing reactivity toward HBr addition:

Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing ΔH° of this reaction. The most negative ΔH° should be listed first. 2,5-dimethyl-1,3-cycloheptadiene, 1,4-dimethyl-1,3-cycloheptadiene, and 3,6-dimethyl-1,4-cycloheptadiene

Draw the LUMO of 1,3,5-hexatriene.

Excluding the horizontal node which is coincident with the molecular plane, how many nodes are present in Ψ₄ of the 1, 3, 5-hexatriene π system?

Draw the HOMO of 1,3,5-hexatriene.

Identify the most stable carbocation.

In the molecular orbital representation of benzene, how many π molecular orbitals are present?

Provide a diagram which depicts the relative energies of the π molecular orbitals of benzene. Show which molecular orbitals are filled in benzene's ground state.

Which of the following is the weakest base?

Which of the following ions is most acidic?

Which species is represented by the following distribution of π electrons in the molecular orbitals and energy levels diagram?

Which π MOs are bonding MOs in the ground state of 1,3,5-hexatriene?

Which of the following is/are the major product(s) of the following reaction?

Which of the following is the strongest acid?

Show how the p orbitals overlap to form the nonbonding π molecular orbital of the allyl system.

Which of the following is the strongest acid?

Identify the most stable carbocation.

Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing ΔH° of this reaction. The most negative ΔH° should be listed first. cis-2-pentene, 2,3-pentadiene, and trans-1,3-pentadiene

Quiz 8: Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Indicate the compound that has the shortest bond length between the two middle carbon atoms.

Among a series of isomeric trienes, the more negative the ΔH° of the hydrogenation reaction of a given triene, the ________ stable it is relative to the others in the isomeric series.

Arrange the following unsaturated hydrocarbons in order of decreasing reactivity toward HBr addition:

Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing ΔH° of this reaction. The most negative ΔH° should be listed first. 2,5-dimethyl-1,3-cycloheptadiene, 1,4-dimethyl-1,3-cycloheptadiene, and 3,6-dimethyl-1,4-cycloheptadiene

Draw the LUMO of 1,3,5-hexatriene.

Excluding the horizontal node which is coincident with the molecular plane, how many nodes are present in Ψ4 of the 1, 3, 5-hexatriene π system?

Draw the HOMO of 1,3,5-hexatriene.

Identify the most stable carbocation.

In the molecular orbital representation of benzene, how many π molecular orbitals are present?

Provide a diagram which depicts the relative energies of the π molecular orbitals of benzene. Show which molecular orbitals are filled in benzene's ground state.

Which of the following is the weakest base?

Which of the following ions is most acidic?

Which species is represented by the following distribution of π electrons in the molecular orbitals and energy levels diagram?

Which π MOs are bonding MOs in the ground state of 1,3,5-hexatriene?

Which of the following is/are the major product(s) of the following reaction?

Which of the following is the strongest acid?

Show how the p orbitals overlap to form the nonbonding π molecular orbital of the allyl system.

Which of the following is the strongest acid?

Identify the most stable carbocation.

Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing ΔH° of this reaction. The most negative ΔH° should be listed first. cis-2-pentene, 2,3-pentadiene, and trans-1,3-pentadiene

Excluding the horizontal node which is coincident with the molecular plane, how many nodes are present in Ψ₄ of the 1, 3, 5-hexatriene π system?