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Week 10: Pericyclic Reactions 1. Draw the intermediates A-C for reactions a and b. Please show the appropriate stereochemistry where necessary. RO hv 28-40 |_ CO₂Me CO₂Me A . . . . (b) Cº. lili A diena MeO₂C Anti-tumour agent Conolin barrelene CO₂M

Week 10: Pericyclic Reactions 1. Draw the intermediates A-C for reactions a and b. Please show the appropriate stereochemistry where necessary. RO hv 28-40 |_ CO₂Me CO₂Me A . . . . (b) Cº. lili A diena MeO₂C Anti-tumour agent Conolin barrelene CO₂M

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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--- ### Week 10: Pericyclic Reactions #### 1. Draw the intermediates A-C for reactions a and b. Please show the appropriate stereochemistry where necessary. **Reaction (a):** - The initial compound is a diene with an RO substituent. - Upon exposure to light ("hv"), it is transformed into intermediate A. - Intermediate A further converts to intermediate B upon exposure to heat ("Δ"). Intermediate B transforms into an anti-tumor agent Cantharidin. **Reaction (b):** - The initial compound is a benzene ring with a CO₂Me substituent. - This compound transforms into intermediate A upon exposure to heat ("Δ"). - Intermediate A further converts to intermediate B. - Intermediate B converts to intermediate C upon exposure to heat ("Δ"). - Intermediate C transforms into the final product, barrelene, with CO₂Me substituent. #### 2. Propose a full mechanism using curvy reaction arrows for the following transformation. [This section shows a starting compound with a ring structure that transforms into another ring structure with a double bond and a carbonyl group arrow pushing is required to depict the full mechanism.] --- This transcription would be included on an educational website aimed at students studying pericyclic reactions. The content outlines the exercises involving drawing intermediates and proposing reaction mechanisms using curvy arrows. Explicit diagrams would be beneficial to illustrate the reactions and mechanisms described. **Note:** For a fully comprehensive understanding, refer to textbooks or supplemental materials detailing reactions, intermediate steps, and stereochemistry in organic chemistry.
Transcribed Image Text:--- ### Week 10: Pericyclic Reactions #### 1. Draw the intermediates A-C for reactions a and b. Please show the appropriate stereochemistry where necessary. **Reaction (a):** - The initial compound is a diene with an RO substituent. - Upon exposure to light ("hv"), it is transformed into intermediate A. - Intermediate A further converts to intermediate B upon exposure to heat ("Δ"). Intermediate B transforms into an anti-tumor agent Cantharidin. **Reaction (b):** - The initial compound is a benzene ring with a CO₂Me substituent. - This compound transforms into intermediate A upon exposure to heat ("Δ"). - Intermediate A further converts to intermediate B. - Intermediate B converts to intermediate C upon exposure to heat ("Δ"). - Intermediate C transforms into the final product, barrelene, with CO₂Me substituent. #### 2. Propose a full mechanism using curvy reaction arrows for the following transformation. [This section shows a starting compound with a ring structure that transforms into another ring structure with a double bond and a carbonyl group arrow pushing is required to depict the full mechanism.] --- This transcription would be included on an educational website aimed at students studying pericyclic reactions. The content outlines the exercises involving drawing intermediates and proposing reaction mechanisms using curvy arrows. Explicit diagrams would be beneficial to illustrate the reactions and mechanisms described. **Note:** For a fully comprehensive understanding, refer to textbooks or supplemental materials detailing reactions, intermediate steps, and stereochemistry in organic chemistry.
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