Show an SN2 mechanism for the following reaction. Include the transition state for the substitution at carbon, with stereochemistry. Use your work to predict the product, including stereochemistry. You don't need to show stereochemistry on phosphorus. Ph;PBr2 HO- H THE
Show an SN2 mechanism for the following reaction. Include the transition state for the substitution at carbon, with stereochemistry. Use your work to predict the product, including stereochemistry. You don't need to show stereochemistry on phosphorus. Ph;PBr2 HO- H THE
Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![**SN2 Reaction Mechanism: Stereochemistry and Transition States**
This section discusses the SN2 reaction mechanism for the specific chemical reaction shown below. The reaction entails the substitution at carbon with stereochemistry, and we will predict the product, focusing on stereochemistry.
---
**Given Reaction:**
\[ \text{Reactant:} \quad \begin{array}{c}
\includegraphics[scale=0.4]{reactant}
\end{array}
+ \text{Ph}_3\text{PBr}_2 \quad \text{(in THF)} \quad \rightarrow \quad \text{Product}
\]
In the above equation:
1. **Reactants**:
- A secondary alcohol (shown in the structure on the left).
- Ph₃PBr₂ as a reagent.
- THF (Tetrahydrofuran) as a solvent.
2. **Mechanism**:
- This is a bimolecular nucleophilic substitution (SN2) reaction.
- **Transition State**: The reaction proceeds through a single, concerted step where the nucleophile attacks the electrophilic carbon from the opposite side, leading to an inversion of configuration at the carbon center.
3. **Stereochemistry**:
- The SN2 mechanism is known for causing inversion of stereochemistry at the carbon where substitution occurs. Specifically, if the original reactant has the OH group attached to a chiral center, the product will have the substituting group (Br) attached with inverted configuration.
In this reaction:
- The hydroxyl group (-OH) on the secondary carbon is first converted to a better leaving group, facilitated by the Ph₃PBr₂.
- Following this, the bromide ion (\( \text{Br}^-\)) attacks the carbon center from the opposite side of the leaving group, resulting in a change of stereochemistry (inversion).
**Note**: You do not need to illustrate the stereochemistry on phosphorus in this mechanism as we are focusing on the carbon center.
Through the discussion of the SN2 mechanism, participants can understand the stereochemical outcomes of these reactions, reinforcing concepts of nucleophilic substitution and transition states in organic chemistry.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F9881b937-b6f3-4fcd-95a2-fb7295b9c7b9%2F8d9f8a1d-4488-435e-842f-ff2dc53cb924%2Fmyb9qu_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**SN2 Reaction Mechanism: Stereochemistry and Transition States**
This section discusses the SN2 reaction mechanism for the specific chemical reaction shown below. The reaction entails the substitution at carbon with stereochemistry, and we will predict the product, focusing on stereochemistry.
---
**Given Reaction:**
\[ \text{Reactant:} \quad \begin{array}{c}
\includegraphics[scale=0.4]{reactant}
\end{array}
+ \text{Ph}_3\text{PBr}_2 \quad \text{(in THF)} \quad \rightarrow \quad \text{Product}
\]
In the above equation:
1. **Reactants**:
- A secondary alcohol (shown in the structure on the left).
- Ph₃PBr₂ as a reagent.
- THF (Tetrahydrofuran) as a solvent.
2. **Mechanism**:
- This is a bimolecular nucleophilic substitution (SN2) reaction.
- **Transition State**: The reaction proceeds through a single, concerted step where the nucleophile attacks the electrophilic carbon from the opposite side, leading to an inversion of configuration at the carbon center.
3. **Stereochemistry**:
- The SN2 mechanism is known for causing inversion of stereochemistry at the carbon where substitution occurs. Specifically, if the original reactant has the OH group attached to a chiral center, the product will have the substituting group (Br) attached with inverted configuration.
In this reaction:
- The hydroxyl group (-OH) on the secondary carbon is first converted to a better leaving group, facilitated by the Ph₃PBr₂.
- Following this, the bromide ion (\( \text{Br}^-\)) attacks the carbon center from the opposite side of the leaving group, resulting in a change of stereochemistry (inversion).
**Note**: You do not need to illustrate the stereochemistry on phosphorus in this mechanism as we are focusing on the carbon center.
Through the discussion of the SN2 mechanism, participants can understand the stereochemical outcomes of these reactions, reinforcing concepts of nucleophilic substitution and transition states in organic chemistry.
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