Brg (2) CHBr Adamantane Br -Br 1-bromoadamantane (3)

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
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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One more time, don't need the entire mechanism. I need the structure of nucleophile 3. If you can't answer this question, that's fine, give it to someone else who can. Thank you.

### Synthesis of Rimantadine

**Introduction:**
Rimantadine was among the first antiviral drugs to be licensed in the United States for use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane through the following sequence of reactions:

#### Step-by-Step Reaction Sequence:

1. **Adamantane to 1-bromoadamantane:**
   - **Reagents:** Br₂
   - **Reaction:** Adamantane reacts with bromine to form 1-bromoadamantane.
   - **Diagram:**
     ```
         ___
       /     \
      /       \
     |   Br     \
     \  /       /
      \___/
     ```
  
2. **1-bromoadamantane to Intermediate:**
   - **Reagents:** CH₂=CHBr, AlBr₃
   - **Reaction:** 1-bromoadamantane reacts with bromoethene in the presence of AlBr₃ to form the intermediate product.
   - **Mechanism Overview:** 
     1. AlBr₃ acts as a Lewis acid to yield carbocation 1.
     2. Bromoethene acts as a nucleophile to give carbocation 2.
     3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2.
   
3. **Intermediate to Triple-bond Intermediate:**
   - **Reagents:** None specified for this step.
   - **Reaction:** The intermediate undergoes a transformation to form a triple-bond intermediate.
   - **Diagram:**
     ```
         ___
       /     \
      /       \
     |   ≡      \
     \  /       /
      \___/
     ```

4. **Triple-bond Intermediate to Intermediate with Ketone:**
   - **Reagents:** None specified for this step.
   - **Reaction:** The triple-bond intermediate undergoes a transformation to form an intermediate with a ketone group.
   - **Diagram:**
     ```
         ___
       /     \
      /       \
     |   CO    \
     \  /       /
      \___/
     ```

5. **Intermediate with Ketone to Rimantadine:**
   - **Reagents:** None specified for this step.
   - **Reaction:** The intermediate with a ketone group changes to form the final product, Rimantadine, which
Transcribed Image Text:### Synthesis of Rimantadine **Introduction:** Rimantadine was among the first antiviral drugs to be licensed in the United States for use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane through the following sequence of reactions: #### Step-by-Step Reaction Sequence: 1. **Adamantane to 1-bromoadamantane:** - **Reagents:** Br₂ - **Reaction:** Adamantane reacts with bromine to form 1-bromoadamantane. - **Diagram:** ``` ___ / \ / \ | Br \ \ / / \___/ ``` 2. **1-bromoadamantane to Intermediate:** - **Reagents:** CH₂=CHBr, AlBr₃ - **Reaction:** 1-bromoadamantane reacts with bromoethene in the presence of AlBr₃ to form the intermediate product. - **Mechanism Overview:** 1. AlBr₃ acts as a Lewis acid to yield carbocation 1. 2. Bromoethene acts as a nucleophile to give carbocation 2. 3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2. 3. **Intermediate to Triple-bond Intermediate:** - **Reagents:** None specified for this step. - **Reaction:** The intermediate undergoes a transformation to form a triple-bond intermediate. - **Diagram:** ``` ___ / \ / \ | ≡ \ \ / / \___/ ``` 4. **Triple-bond Intermediate to Intermediate with Ketone:** - **Reagents:** None specified for this step. - **Reaction:** The triple-bond intermediate undergoes a transformation to form an intermediate with a ketone group. - **Diagram:** ``` ___ / \ / \ | CO \ \ / / \___/ ``` 5. **Intermediate with Ketone to Rimantadine:** - **Reagents:** None specified for this step. - **Reaction:** The intermediate with a ketone group changes to form the final product, Rimantadine, which
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