Br CH2 HBr CH3 Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions -CH3 :Br:

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
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I did the 1st one, Am I doing it right? For the 2nd one, how would you do the arrow notation? please draw it clear and directly on where it is supposed to go.

### Electrophilic Addition Reaction Mechanism with HBr

#### Reaction Overview:

In this step of the reaction mechanism, 1-hexene will react with hydrogen bromide (HBr) to form 2-bromohexane.

#### Chemical Equation:

\[ \text{Cyclopentane-CH}= \text{CH}_2 + \text{HBr} \rightarrow \text{Cyclopentane}-\text{CH}(\text{Br})-\text{CH}_3 \]

#### Mechanistic Details:

1. **Initiation of the Reaction:**
   - The double bond (\( \text{CH}_2 \)) in the cyclopentane structure acts as a nucleophile, reacting with HBr.
   
2. **Intermediate Formation:**
   - The reaction proceeds via the formation of a carbocation intermediate, illustrated as a secondary carbocation in the bottom left structure, where the positively charged carbon (C) is connected to the propane ring.
   - Bromide ion (\( \text{Br}^- \)) is formed as a result of heterolytic cleavage.

#### Arrow-Pushing Instructions:

The reaction mechanism can be depicted using curved arrows to display how electron pairs move during the reaction.
   
3. **Arrow-Pushing Diagram:**
   - Illustrates the nucleophilic attack step where electrons from the π bond (double bond) are used to form a new bond with a hydrogen atom from HBr, leading to the formation of the carbocation intermediate and the bromide ion.
   
4. **Final Step:**
   - The lone pair of electrons on the bromide ion (\( \text{Br}^- \)) will attack the positively charged carbon atom in the carbocation intermediate, resulting in the final product: 2-bromohexane.

#### Diagrams:

1. **Initial Molecules:**
   - Cyclopentane with a double bond connected to a side chain molecule (alkene).
   - HBr molecule (\( \text{H-Br} \)).

2. **Intermediate:**
   - Shows a carbocation (positively charged carbon) with explicit marking.
   - Bromide ion with lone pairs represented by dots (\( \text{..Br^-} \)).

3. **Completion:**
   - Depicts the formation of Bromocyclopentane as a final product after the bromide ion donates its electron pair to the positively charged carbon ion
Transcribed Image Text:### Electrophilic Addition Reaction Mechanism with HBr #### Reaction Overview: In this step of the reaction mechanism, 1-hexene will react with hydrogen bromide (HBr) to form 2-bromohexane. #### Chemical Equation: \[ \text{Cyclopentane-CH}= \text{CH}_2 + \text{HBr} \rightarrow \text{Cyclopentane}-\text{CH}(\text{Br})-\text{CH}_3 \] #### Mechanistic Details: 1. **Initiation of the Reaction:** - The double bond (\( \text{CH}_2 \)) in the cyclopentane structure acts as a nucleophile, reacting with HBr. 2. **Intermediate Formation:** - The reaction proceeds via the formation of a carbocation intermediate, illustrated as a secondary carbocation in the bottom left structure, where the positively charged carbon (C) is connected to the propane ring. - Bromide ion (\( \text{Br}^- \)) is formed as a result of heterolytic cleavage. #### Arrow-Pushing Instructions: The reaction mechanism can be depicted using curved arrows to display how electron pairs move during the reaction. 3. **Arrow-Pushing Diagram:** - Illustrates the nucleophilic attack step where electrons from the π bond (double bond) are used to form a new bond with a hydrogen atom from HBr, leading to the formation of the carbocation intermediate and the bromide ion. 4. **Final Step:** - The lone pair of electrons on the bromide ion (\( \text{Br}^- \)) will attack the positively charged carbon atom in the carbocation intermediate, resulting in the final product: 2-bromohexane. #### Diagrams: 1. **Initial Molecules:** - Cyclopentane with a double bond connected to a side chain molecule (alkene). - HBr molecule (\( \text{H-Br} \)). 2. **Intermediate:** - Shows a carbocation (positively charged carbon) with explicit marking. - Bromide ion with lone pairs represented by dots (\( \text{..Br^-} \)). 3. **Completion:** - Depicts the formation of Bromocyclopentane as a final product after the bromide ion donates its electron pair to the positively charged carbon ion
**Understanding Regioselectivity and Stereoselectivity in Hydride Reduction Reactions**

**1. Introduction**

In organic chemistry, regioselectivity and stereoselectivity are important concepts for understanding how reactions occur and products are formed. This educational module will guide you through explaining the regioselectivity and stereoselectivity of a compound when treated with mercury(II) acetate (Hg(OAc)₂) in water (H₂O), followed by a reduction reaction.

**2. Compound Analysis**

Below is a molecule that we will be focusing on:

![initial compound structure](initial_compound_structure.png)

**3. Task Requirement**
We need to account for the regioselectivity and stereoselectivity observed when this compound is treated with Hg(OAc)₂ in H₂O. This is done by drawing the product formed prior to a subsequent hydride reduction reaction.

**Key Points to Consider:**
- Use wedge and hash bonds ONLY when needed to show reaction stereochemistry.
- If the reaction produces a racemic mixture, just draw one stereoisomer.
- Draw the expanded structure for the acetyl group (Ac) in your answer.

**4. Expected Product Prior to Reduction**

Below is the product formed when the reaction is performed, before the hydride reduction step:

![product structure](product_structure.png)

**5. Explanation of Diagrams**
- **Initial Compound:** The structure illustrates a molecule with a double bond (alkene) which will undergo mercuration.
- **Reaction Product:** The product structure illustrates the addition of an OH (hydroxyl) group to the molecule, which happens in a regioselective and stereoselective manner, owing to the reaction conditions.

**6. Conclusion**

Understanding the regioselectivity and stereoselectivity during chemical reactions allows for precise predictions about the product's formation. By following the task's guidelines and ensuring accurate representation of stereochemistry, you can gain deeper insights into organic reaction mechanisms.

**7. Further Reading**
For a more detailed understanding, refer to textbooks on organic reaction mechanisms, particularly those that focus on alkene addition reactions and stereochemistry.

Navigational Links:
- **Previous**
- **Next**
Transcribed Image Text:**Understanding Regioselectivity and Stereoselectivity in Hydride Reduction Reactions** **1. Introduction** In organic chemistry, regioselectivity and stereoselectivity are important concepts for understanding how reactions occur and products are formed. This educational module will guide you through explaining the regioselectivity and stereoselectivity of a compound when treated with mercury(II) acetate (Hg(OAc)₂) in water (H₂O), followed by a reduction reaction. **2. Compound Analysis** Below is a molecule that we will be focusing on: ![initial compound structure](initial_compound_structure.png) **3. Task Requirement** We need to account for the regioselectivity and stereoselectivity observed when this compound is treated with Hg(OAc)₂ in H₂O. This is done by drawing the product formed prior to a subsequent hydride reduction reaction. **Key Points to Consider:** - Use wedge and hash bonds ONLY when needed to show reaction stereochemistry. - If the reaction produces a racemic mixture, just draw one stereoisomer. - Draw the expanded structure for the acetyl group (Ac) in your answer. **4. Expected Product Prior to Reduction** Below is the product formed when the reaction is performed, before the hydride reduction step: ![product structure](product_structure.png) **5. Explanation of Diagrams** - **Initial Compound:** The structure illustrates a molecule with a double bond (alkene) which will undergo mercuration. - **Reaction Product:** The product structure illustrates the addition of an OH (hydroxyl) group to the molecule, which happens in a regioselective and stereoselective manner, owing to the reaction conditions. **6. Conclusion** Understanding the regioselectivity and stereoselectivity during chemical reactions allows for precise predictions about the product's formation. By following the task's guidelines and ensuring accurate representation of stereochemistry, you can gain deeper insights into organic reaction mechanisms. **7. Further Reading** For a more detailed understanding, refer to textbooks on organic reaction mechanisms, particularly those that focus on alkene addition reactions and stereochemistry. Navigational Links: - **Previous** - **Next**
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