Consider the structure (6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene of (6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene, which can undergo an electrocyclic ring opening. The concerted electron shifts result in a highly stereoselective product. The configuration of the product depends on whether it is a thermal reaction or a photochemical reaction. Predict the thermal and photochemical outcomes of this reaction.
Consider the structure (6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene of (6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene, which can undergo an electrocyclic ring opening. The concerted electron shifts result in a highly stereoselective product. The configuration of the product depends on whether it is a thermal reaction or a photochemical reaction. Predict the thermal and photochemical outcomes of this reaction.
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.3: Stereochemistry Of Thermal Electrocyclic Reactions
Problem 3P
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![Consider the structure
(6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene
of (6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene,
which can undergo an electrocyclic ring opening.
The concerted electron shifts result in a highly
stereoselective product. The configuration of the product
depends on whether it is a thermal reaction or a
photochemical reaction. Predict the thermal and
photochemical outcomes of this reaction.
Draw the thermal product.
Draw the photochemical product.
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Transcribed Image Text:Consider the structure
(6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene
of (6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene,
which can undergo an electrocyclic ring opening.
The concerted electron shifts result in a highly
stereoselective product. The configuration of the product
depends on whether it is a thermal reaction or a
photochemical reaction. Predict the thermal and
photochemical outcomes of this reaction.
Draw the thermal product.
Draw the photochemical product.
Erase
Select
Draw
Rings
More
Erase
Select
Draw
Rings
More
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