by the number of the third intermediate, etc., until you have selected the correct intermediates and place order for the mechanism. An example of the correct answer format would be 231 if you thought intermediate #2 should come first, followed by intermediate #3, and then lastly, intermediate #1. Again, not all of the intermediates are included in this mechanism, so it might be a good idea to try to work it out first on your scratch paper. Do not add any spaces in your answer. HCI :0₁ mit HO CH₂Cl₂ (solvent) Ⓒ Intermediate 11 Intermediate 2 ✪ Intermediate 4 Intermediate 5 HO HO : 0 Intermediate 3 Intermediate 6
by the number of the third intermediate, etc., until you have selected the correct intermediates and place order for the mechanism. An example of the correct answer format would be 231 if you thought intermediate #2 should come first, followed by intermediate #3, and then lastly, intermediate #1. Again, not all of the intermediates are included in this mechanism, so it might be a good idea to try to work it out first on your scratch paper. Do not add any spaces in your answer. HCI :0₁ mit HO CH₂Cl₂ (solvent) Ⓒ Intermediate 11 Intermediate 2 ✪ Intermediate 4 Intermediate 5 HO HO : 0 Intermediate 3 Intermediate 6
Chapter3: Mechanisms
Section: Chapter Questions
Problem 28EQ
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Question
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![**Title: Mechanistic Steps in Organic Reactions**
**Problem Statement:**
The reaction below requires several mechanistic steps. Six different intermediates are shown below. Some are involved in the mechanism and some are not. Your job is to pick the correct intermediates and put them in the correct order. Your answer should be formatted using the number of the first intermediate, followed by the number of the second intermediate, followed by the number of the third intermediate, etc., until you have selected the correct intermediates and placed them in the correct order for the mechanism.
An example of the correct answer format would be 231 if you thought intermediate #2 should come first, followed by intermediate #3, and then lastly, intermediate #1. Again, not all of the intermediates are included in this mechanism, so it might be a good idea to try to work it out first on your scratch paper. Do not add any spaces in your answer.
**Reaction Conditions:**
- Reagent: HCl
- Solvent: CH₂Cl₂ (dichloromethane)
**Intermediates:**
1. **Intermediate 1**: A linear molecule with an -OH and a -OH attached to the first and fifth carbons, respectively.
![Intermediate 1](URL)
2. **Intermediate 2**: Similar to Intermediate 1 but with a different spatial arrangement making it zigzag.
![Intermediate 2](URL)
3. **Intermediate 3**: A cyclic structure with possible charge separation.
![Intermediate 3](URL)
4. **Intermediate 4**: Another linear molecule but with different functional group positioning.
![Intermediate 4](URL)
5. **Intermediate 5**: A structure with both linear and branched segments incorporating an -OH.
![Intermediate 5](URL)
6. **Intermediate 6**: A long linear molecule with two -OH groups far apart from each other.
![Intermediate 6](URL)
**Task:**
- Identify and sequence the correct intermediates involved in the reaction path.
Remember, your final answer should clearly outline the sequence in a continuous manner (e.g., 453) without spaces.
*Diagrams:*
The diagrams of intermediates are provided above for visual reference, ensuring correct identification and sequence determination of the reaction intermediates.
This educational exercise helps in understanding the sequence of steps involved in organic reaction mechanisms, crucial for](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F2b8d26a8-87eb-4d55-9239-418c1bd04690%2F51c3b9e2-8b41-4df0-aa63-6e5959830bbd%2Fdm6exrl_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Title: Mechanistic Steps in Organic Reactions**
**Problem Statement:**
The reaction below requires several mechanistic steps. Six different intermediates are shown below. Some are involved in the mechanism and some are not. Your job is to pick the correct intermediates and put them in the correct order. Your answer should be formatted using the number of the first intermediate, followed by the number of the second intermediate, followed by the number of the third intermediate, etc., until you have selected the correct intermediates and placed them in the correct order for the mechanism.
An example of the correct answer format would be 231 if you thought intermediate #2 should come first, followed by intermediate #3, and then lastly, intermediate #1. Again, not all of the intermediates are included in this mechanism, so it might be a good idea to try to work it out first on your scratch paper. Do not add any spaces in your answer.
**Reaction Conditions:**
- Reagent: HCl
- Solvent: CH₂Cl₂ (dichloromethane)
**Intermediates:**
1. **Intermediate 1**: A linear molecule with an -OH and a -OH attached to the first and fifth carbons, respectively.
![Intermediate 1](URL)
2. **Intermediate 2**: Similar to Intermediate 1 but with a different spatial arrangement making it zigzag.
![Intermediate 2](URL)
3. **Intermediate 3**: A cyclic structure with possible charge separation.
![Intermediate 3](URL)
4. **Intermediate 4**: Another linear molecule but with different functional group positioning.
![Intermediate 4](URL)
5. **Intermediate 5**: A structure with both linear and branched segments incorporating an -OH.
![Intermediate 5](URL)
6. **Intermediate 6**: A long linear molecule with two -OH groups far apart from each other.
![Intermediate 6](URL)
**Task:**
- Identify and sequence the correct intermediates involved in the reaction path.
Remember, your final answer should clearly outline the sequence in a continuous manner (e.g., 453) without spaces.
*Diagrams:*
The diagrams of intermediates are provided above for visual reference, ensuring correct identification and sequence determination of the reaction intermediates.
This educational exercise helps in understanding the sequence of steps involved in organic reaction mechanisms, crucial for
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