Profen tran, er g to oH meinsria N. HO in H. H.

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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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The purple pathway: the oxygen - flow to the C-O bond, then from the C=C bond to the carbon atom, then the water molecule.

 

I do not understand why cant the electrons flow from the oxygen - to the water directly AND why cant electrons flow from C=c to the water molecule , but have to land on a carbon atom first before flowing to water.

#### Stepwise Mechanism of the Synthesis of Strychnine

In this section, we will explore the detailed mechanism of strychnine synthesis as elucidated by the prominent work of R.B. Woodward. We will examine the transformation of intermediate 1 into strychnine (6) through the intermediates 2-5. The mechanism illustrates various proton transfers, cyclization steps, and bond formation/breaking. Let's dive into the key steps involved:

1. **Transformation of Intermediate 1 to Intermediate 2:**
   - In the first figure (circled in yellow), a proton transfer occurs. This is indicated by the arrow which starts from the nitrogen and ends at the oxygen to form a hydroxyl group (OH).

2. **Transition from Intermediate 2 to Intermediate 3:**
   - The second figure (blue circle) shows another proton transfer leading to the formation of an intermediate structure. This step involves the movement of a proton (H) from one position to another, reshaping the molecule.

3. **Formation of Intermediate 4:**
   - In the third figure, further rearrangements are indicated with curved arrows that show electron movement leading to the structure of intermediate 4.

4. **Conversion of Intermediate 4 to Intermediate 5:**
   - The fourth figure (highlighted in pink) illustrates the nucleophilic attack and subsequent electron relocation that leads to intermediate 5. Notice the involvement of key functional groups in this step.

5. **Final Transformation to Strychnine (6):**
   - The final figure shows the formation of strychnine (6). This step confirms the cyclization and proton shift involved in constructing the strychnine molecule. 

**Instructions for Drawing Curved Arrows and Sequence Analysis:**
- Draw all the curved arrows that indicate the movement of electrons (proton transfers, nucleophilic attacks) throughout the entire transformation of 1 to 6.
- Identify and articulate the entire sequence of transformations, providing a clear description of each arrow-pushing pattern.
- For the critical step where intermediate 4 transforms to 5, identify the nucleophilic centers and explain how electrons interact to lead to the formation of intermediate 5. Use resonance structures to demonstrate these interactions wherever applicable.

**Note on the Handwritten Elements:**
- Annotations such as "proton transfer to OH" and arrow movements are drawn to reflect key mechanistic steps in the synthesis.
Transcribed Image Text:#### Stepwise Mechanism of the Synthesis of Strychnine In this section, we will explore the detailed mechanism of strychnine synthesis as elucidated by the prominent work of R.B. Woodward. We will examine the transformation of intermediate 1 into strychnine (6) through the intermediates 2-5. The mechanism illustrates various proton transfers, cyclization steps, and bond formation/breaking. Let's dive into the key steps involved: 1. **Transformation of Intermediate 1 to Intermediate 2:** - In the first figure (circled in yellow), a proton transfer occurs. This is indicated by the arrow which starts from the nitrogen and ends at the oxygen to form a hydroxyl group (OH). 2. **Transition from Intermediate 2 to Intermediate 3:** - The second figure (blue circle) shows another proton transfer leading to the formation of an intermediate structure. This step involves the movement of a proton (H) from one position to another, reshaping the molecule. 3. **Formation of Intermediate 4:** - In the third figure, further rearrangements are indicated with curved arrows that show electron movement leading to the structure of intermediate 4. 4. **Conversion of Intermediate 4 to Intermediate 5:** - The fourth figure (highlighted in pink) illustrates the nucleophilic attack and subsequent electron relocation that leads to intermediate 5. Notice the involvement of key functional groups in this step. 5. **Final Transformation to Strychnine (6):** - The final figure shows the formation of strychnine (6). This step confirms the cyclization and proton shift involved in constructing the strychnine molecule. **Instructions for Drawing Curved Arrows and Sequence Analysis:** - Draw all the curved arrows that indicate the movement of electrons (proton transfers, nucleophilic attacks) throughout the entire transformation of 1 to 6. - Identify and articulate the entire sequence of transformations, providing a clear description of each arrow-pushing pattern. - For the critical step where intermediate 4 transforms to 5, identify the nucleophilic centers and explain how electrons interact to lead to the formation of intermediate 5. Use resonance structures to demonstrate these interactions wherever applicable. **Note on the Handwritten Elements:** - Annotations such as "proton transfer to OH" and arrow movements are drawn to reflect key mechanistic steps in the synthesis.
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