2. Predict the stereochemistry for the following reduction. OH 1. LIAIH4, Et,0 Me Me Me Me 2. H3O+ (quench) Me OSiPh2(t-Bu) Me OSiPh2(t-Bu) Draw the two competing transition structures (L. Overman, Tetrahedron Lett. 1982, 23, 2355.).
Electronic Effects
The effect of electrons that are located in the chemical bonds within the atoms of the molecule is termed an electronic effect. The electronic effect is also explained as the effect through which the reactivity of the compound in one portion is controlled by the electron repulsion or attraction producing in another portion of the molecule.
Drawing Resonance Forms
In organic chemistry, resonance may be a mental exercise that illustrates the delocalization of electrons inside molecules within the valence bond theory of octet bonding. It entails creating several Lewis structures that, when combined, reflect the molecule's entire electronic structure. One Lewis diagram cannot explain the bonding (lone pair, double bond, octet) elaborately. A hybrid describes a combination of possible resonance structures that represents the entire delocalization of electrons within the molecule.
Using Molecular Structure To Predict Equilibrium
Equilibrium does not always imply an equal presence of reactants and products. This signifies that the reaction reaches a point when reactant and product quantities remain constant as the rate of forward and backward reaction is the same. Molecular structures of various compounds can help in predicting equilibrium.
Can you help me on this problem?
![**Predict the Stereochemistry for the Following Reduction**
Given the following chemical reaction, predict the stereochemistry of the product:
### Reaction:
- **Substrate**:
- A ketone with the structure:
\[
\begin{array}{c}
\\
\text{O} \\
\| \\
\text{-Me-C=\text{C(CH}_3)}_2 \text{-OSiPh}_2\text{(t-Bu)}\\
\\
\end{array}
\]
- Additional groups attached: Methyl (Me), Trimethylsilyl (OSiPh₂(t-Bu))
- **Reagents**:
1. **LiAlH₄**, **Et₂O**
2. **H₃O⁺** (quench)
### Expected Product:
- The carbonyl group is reduced to an alcohol, with the new structure:
\[
\begin{array}{c}
\\
\text{OH} \\
| \\
\text{-Me-C(\text{Me})-CH-OH-OSiPh}_2\text{(t-Bu)} \\
\\
\end{array}
\]
### Task:
Draw the two competing transition structures based on the addition of hydride to the ketone.
**Reference**: L. Overman, *Tetrahedron Lett.* 1982, 23, 2355.
In this reaction, stereochemical outcomes depend on the mode of approach of the hydride ion, which can lead to different stereoisomers. Analyze the specific stereochemistry that will result from each transition state and consider how steric and electronic effects influence this process.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F894efb48-d5df-469e-a64d-744d0e0972f9%2F10c5e70d-3db7-40fd-92c9-894ac80dac3c%2Fpbdv3878_processed.png&w=3840&q=75)
Trending now
This is a popular solution!
Step by step
Solved in 3 steps with 2 images
