Be sure to answer all parts. Draw a stepwise mechanism for the following reaction: Part 1 out of 2 CH₂ CH3 H-Br finish structure ... OH ↑ HBr draw structure ... CH3 Br O O HOBr HO™ H₂O HBr Br

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#6r Daw a stepwise mechanism for the following reaction:

**Title: Reaction Mechanism for Conversion of Alcohol to Haloalkane**

**Objective:**

Draw a stepwise mechanism for the conversion reaction: 

An alcohol group is converted to a bromoalkane using hydrobromic acid (HBr).

---

**Step 1: Identify the Reactants and Products**

- **Reactant:** The starting compound is a structure featuring a secondary alcohol. It consists of a carbon chain with a hydroxyl (OH) group and a methyl group (CH₃) attached to the chiral center.
- **Reagent:** Hydrobromic acid (HBr).
- **Product:** The resulting compound is a bromoalkane, where the hydroxyl group has been replaced by a bromine (Br).

**Part 1 of 2: Initial Interaction**

1. **Initial Structure:**
   - Show the complete structure for reactants, including partial charges and lone pairs if applicable.
   - The alcohol and HBr are shown close together, indicating a possible site of interaction. The oxygen in the OH group is likely to be a site of nucleophilic attack.

2. **Mechanistic Step:**
   - **Protonation of Alcohol:** The hydroxyl group (OH) interacts with HBr. The H⁺ from HBr is attracted to the lone pair on the oxygen atom of the alcohol.

**Diagram Explanation:**

- The **left box** contains the alcohol interacting with HBr.
- The **right box** is left incomplete, prompting the user to draw the structure of the intermediate or transition state.
- **Choices for By-products:**
  - Various potential by-products of this step are listed on the right, including:
    - HOBr
    - HO⁻
    - H₂O
    - HBr
    - Br⁻
    
The correct product of the first step will be the formation of water (H₂O) as a leaving group from the protonated alcohol, eventually leading to the substitution by Br⁻.

**Conclusion:**

In this step, you facilitated the reaction by protonating the alcohol, allowing it to become a better leaving group (water). Now, determine the subsequent steps that lead to the formation of the bromoalkane. Continue to Part 2 to complete the mechanism.
Transcribed Image Text:**Title: Reaction Mechanism for Conversion of Alcohol to Haloalkane** **Objective:** Draw a stepwise mechanism for the conversion reaction: An alcohol group is converted to a bromoalkane using hydrobromic acid (HBr). --- **Step 1: Identify the Reactants and Products** - **Reactant:** The starting compound is a structure featuring a secondary alcohol. It consists of a carbon chain with a hydroxyl (OH) group and a methyl group (CH₃) attached to the chiral center. - **Reagent:** Hydrobromic acid (HBr). - **Product:** The resulting compound is a bromoalkane, where the hydroxyl group has been replaced by a bromine (Br). **Part 1 of 2: Initial Interaction** 1. **Initial Structure:** - Show the complete structure for reactants, including partial charges and lone pairs if applicable. - The alcohol and HBr are shown close together, indicating a possible site of interaction. The oxygen in the OH group is likely to be a site of nucleophilic attack. 2. **Mechanistic Step:** - **Protonation of Alcohol:** The hydroxyl group (OH) interacts with HBr. The H⁺ from HBr is attracted to the lone pair on the oxygen atom of the alcohol. **Diagram Explanation:** - The **left box** contains the alcohol interacting with HBr. - The **right box** is left incomplete, prompting the user to draw the structure of the intermediate or transition state. - **Choices for By-products:** - Various potential by-products of this step are listed on the right, including: - HOBr - HO⁻ - H₂O - HBr - Br⁻ The correct product of the first step will be the formation of water (H₂O) as a leaving group from the protonated alcohol, eventually leading to the substitution by Br⁻. **Conclusion:** In this step, you facilitated the reaction by protonating the alcohol, allowing it to become a better leaving group (water). Now, determine the subsequent steps that lead to the formation of the bromoalkane. Continue to Part 2 to complete the mechanism.
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