Draw the detailed mechanisms for the following transformations. H3C 0CH 3 (1.5 equiv) OCH3 then reflux, 5h 1. 56% CICH,CH,CI, hv 19.5h N2 N. CH3 N. 3. Вос Вос OH
Draw the detailed mechanisms for the following transformations. H3C 0CH 3 (1.5 equiv) OCH3 then reflux, 5h 1. 56% CICH,CH,CI, hv 19.5h N2 N. CH3 N. 3. Вос Вос OH
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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
Transcribed Image Text:### Transformation Mechanism Exercise
**Objective:** Draw the detailed mechanisms for the following transformations.
1. **Reaction:**
- **Starting Material:** An indole derivative with a Boc-protected nitrogen and a diazo group.
- **Reagent:** 1.5 equivalents of an alkyne (CH₃C≡COCH₃).
- **Condition:** Dichloromethane (ClCH₂CH₂Cl) under light (hv) for 19.5 hours.
- **Intermediate Process:** Followed by reflux for 5 hours.
- **Yield:** 56%
- **Product:** A substituted indole featuring methoxy and hydroxyl groups at its benzene ring and an N-Boc group.
**Analysis:**
- The reaction begins with a photochemical step where diazo compound reacts with an alkyne.
- The process involves carbene generation and subsequent reactions for cyclization.
- Reflux stage drives further chemical changes, including substitution and rearrangement.
- Monitor the integration of groups such as methoxy, hydroxyl, and acetylene was crucial for transformation.
The structure and naming of organic molecules like these highlight significant transformations in complex organic synthesis, useful for advanced organic chemistry education.
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