**Reduction Reaction Stereochemistry** **Reaction Details:** - **Substrate:** - Molecular structure: a compound with a ketone group (C=O) and an OSiPh₂(t-Bu) protecting group. - Features: Methyl groups (Me) are attached, including a double bond (alkene). - **Reagents and Conditions:** 1. **LiAlH₄, Et₂O:** Lithium aluminum hydride in diethyl ether is used for the reduction of the carbonyl (C=O) group. 2. **H₃O⁺ (quench):** An acidic workup to quench the reaction. - **Product:** - Molecular structure: An alcohol (OH) results from the reduction of the ketone. - Notable Stereochemistry: Indicated with an asterisk (*), highlighting the need to determine the stereochemistry around this chiral center. **Task:** - Predict the stereochemistry for the reduction product. - Draw the two competing transition states for the given reaction setup. **Reference:** - L. Overman, Tetrahedron Letters, 1982, Vol. 23, Page 2355. This literature provides insight into the stereochemistry factors influencing the transition state of this specific reaction. The challenge is to determine which stereochemical path is favored during the reduction, considering potential steric and electronic effects within the transition state.
**Reduction Reaction Stereochemistry** **Reaction Details:** - **Substrate:** - Molecular structure: a compound with a ketone group (C=O) and an OSiPh₂(t-Bu) protecting group. - Features: Methyl groups (Me) are attached, including a double bond (alkene). - **Reagents and Conditions:** 1. **LiAlH₄, Et₂O:** Lithium aluminum hydride in diethyl ether is used for the reduction of the carbonyl (C=O) group. 2. **H₃O⁺ (quench):** An acidic workup to quench the reaction. - **Product:** - Molecular structure: An alcohol (OH) results from the reduction of the ketone. - Notable Stereochemistry: Indicated with an asterisk (*), highlighting the need to determine the stereochemistry around this chiral center. **Task:** - Predict the stereochemistry for the reduction product. - Draw the two competing transition states for the given reaction setup. **Reference:** - L. Overman, Tetrahedron Letters, 1982, Vol. 23, Page 2355. This literature provides insight into the stereochemistry factors influencing the transition state of this specific reaction. The challenge is to determine which stereochemical path is favored during the reduction, considering potential steric and electronic effects within the transition state.
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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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:**Reduction Reaction Stereochemistry**
**Reaction Details:**
- **Substrate:**
- Molecular structure: a compound with a ketone group (C=O) and an OSiPh₂(t-Bu) protecting group.
- Features: Methyl groups (Me) are attached, including a double bond (alkene).
- **Reagents and Conditions:**
1. **LiAlH₄, Et₂O:** Lithium aluminum hydride in diethyl ether is used for the reduction of the carbonyl (C=O) group.
2. **H₃O⁺ (quench):** An acidic workup to quench the reaction.
- **Product:**
- Molecular structure: An alcohol (OH) results from the reduction of the ketone.
- Notable Stereochemistry: Indicated with an asterisk (*), highlighting the need to determine the stereochemistry around this chiral center.
**Task:**
- Predict the stereochemistry for the reduction product.
- Draw the two competing transition states for the given reaction setup.
**Reference:**
- L. Overman, Tetrahedron Letters, 1982, Vol. 23, Page 2355. This literature provides insight into the stereochemistry factors influencing the transition state of this specific reaction.
The challenge is to determine which stereochemical path is favored during the reduction, considering potential steric and electronic effects within the transition state.
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