Question 1

Provide a picture of the HOMO of 1,3,5-hexatriene.

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Question 2

Predict the major product of the following reaction:

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Question 3

What are the structures of A, B, and C?

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Question 4

Provide a picture of the LUMO of 1,3,5-hexatriene.

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Question 5

The following [3+2] cycloaddition was reported in Organic Letters, 2011, 402. Predict whether the reaction would be thermally or photochemically promoted. Justify your answer by showing overlap of the correct molecular orbitals. Assume the alkene is the electrophile.

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Question 6

Provide the structure of the major organic product in the following reaction.

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Question 7

Is the thermal [4+2] cycloaddition between allyl anion and ethylene an allowed one? To answer, draw the HOMO of allyl anion and the LUMO of ethylene, and comment on the symmetry match of the two.

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Question 8

Provide the structure of the major organic product in the following reaction.

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Question 9

The following Diels-Alder reaction was featured in Tet. Lett. $\textbf{    2011,     }$  960. Predict the structure of the starting materials.

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Question 10

Provide the major organic product of the following reaction.

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Question 11

Assuming kinetic conditions, draw the major product of the reaction below. Include
correct stereochemistry.

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Question 12

Why does the diene shown below fail to undergo a Diels-Alder reaction with even the most reactive dienophiles?

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Question 13

Assuming kinetic conditions, provide the correct stereochemistry and regiochemistry of the major product of the following reaction.

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Question 14

What characterizes a pericyclic reaction?

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Question 15

Predict the outcome of the reaction shown below.

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Question 16

Indicate whether the following cyclization, conducted under thermal conditions, is symmetry allowed. Justify your answer by showing whether the overlapping orbitals in the transition state generate a symmetry-allowed or symmetry-forbidden scenario. Treat ethylene as the nucleophile.

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Question 17

Consider the possible thermal [4+4] cycloaddition of two molecules of 1,3-butadiene to generate cycloocta-1,5-diene. Show the HOMO/LUMO interaction which would result, and use this interaction to predict whether the proposed cycloaddition could occur.

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Question 18

Dicylopentadiene results when cyclopentadiene reacts with itself in a Diels-Alder reaction. Provide the structure of dicyclopentadiene. Pay particular attention to stereochemical detail.

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Question 19

Why does the (E,E)-isomer of 2,4-hexadiene react much more rapidly with dienophiles than does the (Z,Z)-isomer?

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Question 20

Provide the major organic product of the following reaction.

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Quiz 15: Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Provide a picture of the HOMO of 1,3,5-hexatriene.

Predict the major product of the following reaction:

What are the structures of A, B, and C?

Provide a picture of the LUMO of 1,3,5-hexatriene.

The following [3+2] cycloaddition was reported in Organic Letters, 2011, 402. Predict whether the reaction would be thermally or photochemically promoted. Justify your answer by showing overlap of the correct molecular orbitals. Assume the alkene is the electrophile.

Provide the structure of the major organic product in the following reaction.

Is the thermal [4+2] cycloaddition between allyl anion and ethylene an allowed one? To answer, draw the HOMO of allyl anion and the LUMO of ethylene, and comment on the symmetry match of the two.

Provide the structure of the major organic product in the following reaction.

The following Diels-Alder reaction was featured in Tet. Lett. $\textbf{ 2011, }$ 960. Predict the structure of the starting materials. $The following Diels-Alder reaction was featured in Tet. Lett. \textbf{ 2011, } 960. Predict the structure of the starting materials.$

Provide the major organic product of the following reaction.

Assuming kinetic conditions, draw the major product of the reaction below. Include correct stereochemistry.

Why does the diene shown below fail to undergo a Diels-Alder reaction with even the most reactive dienophiles?

Assuming kinetic conditions, provide the correct stereochemistry and regiochemistry of the major product of the following reaction.

What characterizes a pericyclic reaction?

Predict the outcome of the reaction shown below.

Indicate whether the following cyclization, conducted under thermal conditions, is symmetry allowed. Justify your answer by showing whether the overlapping orbitals in the transition state generate a symmetry-allowed or symmetry-forbidden scenario. Treat ethylene as the nucleophile.

Consider the possible thermal [4+4] cycloaddition of two molecules of 1,3-butadiene to generate cycloocta-1,5-diene. Show the HOMO/LUMO interaction which would result, and use this interaction to predict whether the proposed cycloaddition could occur.

Dicylopentadiene results when cyclopentadiene reacts with itself in a Diels-Alder reaction. Provide the structure of dicyclopentadiene. Pay particular attention to stereochemical detail.

Why does the (E,E)-isomer of 2,4-hexadiene react much more rapidly with dienophiles than does the (Z,Z)-isomer?

Provide the major organic product of the following reaction.

Quiz 15: Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Provide a picture of the HOMO of 1,3,5-hexatriene.

Predict the major product of the following reaction:

What are the structures of A, B, and C?

Provide a picture of the LUMO of 1,3,5-hexatriene.

The following [3+2] cycloaddition was reported in Organic Letters, 2011, 402. Predict whether the reaction would be thermally or photochemically promoted. Justify your answer by showing overlap of the correct molecular orbitals. Assume the alkene is the electrophile.

Provide the structure of the major organic product in the following reaction.

Is the thermal [4+2] cycloaddition between allyl anion and ethylene an allowed one? To answer, draw the HOMO of allyl anion and the LUMO of ethylene, and comment on the symmetry match of the two.

Provide the structure of the major organic product in the following reaction.

The following Diels-Alder reaction was featured in Tet. Lett. 2011, \textbf{ 2011, } 2011, 960. Predict the structure of the starting materials.

Provide the major organic product of the following reaction.

Assuming kinetic conditions, draw the major product of the reaction below. Include correct stereochemistry.

Why does the diene shown below fail to undergo a Diels-Alder reaction with even the most reactive dienophiles?

Assuming kinetic conditions, provide the correct stereochemistry and regiochemistry of the major product of the following reaction.

What characterizes a pericyclic reaction?

Predict the outcome of the reaction shown below.

Indicate whether the following cyclization, conducted under thermal conditions, is symmetry allowed. Justify your answer by showing whether the overlapping orbitals in the transition state generate a symmetry-allowed or symmetry-forbidden scenario. Treat ethylene as the nucleophile.

Consider the possible thermal [4+4] cycloaddition of two molecules of 1,3-butadiene to generate cycloocta-1,5-diene. Show the HOMO/LUMO interaction which would result, and use this interaction to predict whether the proposed cycloaddition could occur.

Dicylopentadiene results when cyclopentadiene reacts with itself in a Diels-Alder reaction. Provide the structure of dicyclopentadiene. Pay particular attention to stereochemical detail.

Why does the (E,E)-isomer of 2,4-hexadiene react much more rapidly with dienophiles than does the (Z,Z)-isomer?

Provide the major organic product of the following reaction.

The following Diels-Alder reaction was featured in Tet. Lett. $\textbf{ 2011, }$ 960. Predict the structure of the starting materials. $The following Diels-Alder reaction was featured in Tet. Lett. \textbf{ 2011, } 960. Predict the structure of the starting materials.$