Draw the missing organic structures in the following multistep synthesis. Show all structures at physiological pH (pH = 7.4). Ignore any inorganic byproducts formed. HO H3N, Select to Draw Fmoc-Cl Na2CO3, H₂O piperidine Select to Draw Met-OBn DCC Select to Draw
Draw the missing organic structures in the following multistep synthesis. Show all structures at physiological pH (pH = 7.4). Ignore any inorganic byproducts formed. HO H3N, Select to Draw Fmoc-Cl Na2CO3, H₂O piperidine Select to Draw Met-OBn DCC Select to Draw
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
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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![**Multistep Organic Synthesis**
**Objective:** Draw the missing organic structures in the following multistep synthesis. Show all structures at physiological pH (pH = 7.4). Ignore any inorganic byproducts formed.
**Reactions and Steps:**
1. **Starting Compound:**
- Structure: Depicts an aromatic amino acid with an aldehyde group, a carboxylate, and a phenolic hydroxy group.
2. **Step 1:**
- **Reagents:** Fmoc-Cl, Na₂CO₃, H₂O
- **Action:** Addition of Fmoc (9-fluorenylmethoxycarbonyl) group occurs through reaction with Fmoc-Cl. Na₂CO₃, H₂O serves to maintain a basic environment where necessary.
3. **Intermediate Structure:**
- Contains a placeholder (dashed box) where the product after Step 1 needs to be drawn.
4. **Step 2:**
- **Reagents:** Met-OBn, DCC
- **Action:** Introduction of a methionine derivative (Met-OBn) as a coupling partner using DCC (dicyclohexylcarbodiimide) as a coupling agent. This typically facilitates the formation of an amide bond.
5. **Intermediate Structure:**
- Contains a placeholder (dashed box) where the product after Step 2 needs to be drawn.
6. **Step 3:**
- **Reagent:** Piperidine
- **Action:** Removal of the Fmoc protecting group using piperidine. Piperidine cleaves Fmoc groups liberating the free amine.
7. **Final Structure:**
- Contains a placeholder (dashed box) where the final product after Step 3 needs to be drawn.
**Note:** Each step builds upon the previous to create an increasingly complex organic molecule by adding or modifying functional groups while maintaining conditions suitable at physiological pH.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ffee5a196-0e10-4c2e-9c7f-7471e7c61611%2Fe30b67ac-749a-4cf9-9f5c-90e284c80a24%2F9r1iqlb_processed.png&w=3840&q=75)
Transcribed Image Text:**Multistep Organic Synthesis**
**Objective:** Draw the missing organic structures in the following multistep synthesis. Show all structures at physiological pH (pH = 7.4). Ignore any inorganic byproducts formed.
**Reactions and Steps:**
1. **Starting Compound:**
- Structure: Depicts an aromatic amino acid with an aldehyde group, a carboxylate, and a phenolic hydroxy group.
2. **Step 1:**
- **Reagents:** Fmoc-Cl, Na₂CO₃, H₂O
- **Action:** Addition of Fmoc (9-fluorenylmethoxycarbonyl) group occurs through reaction with Fmoc-Cl. Na₂CO₃, H₂O serves to maintain a basic environment where necessary.
3. **Intermediate Structure:**
- Contains a placeholder (dashed box) where the product after Step 1 needs to be drawn.
4. **Step 2:**
- **Reagents:** Met-OBn, DCC
- **Action:** Introduction of a methionine derivative (Met-OBn) as a coupling partner using DCC (dicyclohexylcarbodiimide) as a coupling agent. This typically facilitates the formation of an amide bond.
5. **Intermediate Structure:**
- Contains a placeholder (dashed box) where the product after Step 2 needs to be drawn.
6. **Step 3:**
- **Reagent:** Piperidine
- **Action:** Removal of the Fmoc protecting group using piperidine. Piperidine cleaves Fmoc groups liberating the free amine.
7. **Final Structure:**
- Contains a placeholder (dashed box) where the final product after Step 3 needs to be drawn.
**Note:** Each step builds upon the previous to create an increasingly complex organic molecule by adding or modifying functional groups while maintaining conditions suitable at physiological pH.
![This diagram represents a chemical reaction scheme involving several steps and reagents.
1. **Top Right Reaction:**
- **Reagents:** Met-OBn and DCC
- An arrow is pointing from these reagents to a box labeled “Select to Draw,” indicating that a reaction occurs here, though the specific reaction or product is not shown.
2. **Middle Horizontal Reaction:**
- **Reagent:** Piperidine
- An arrow points from the right “Select to Draw” box to the left “Select to Draw” box, indicating a secondary reaction or transformation facilitated by piperidine.
3. **Bottom Vertical Reaction:**
- **Reagents:** H₂ and Pd-C
- An arrow pointing down from the left “Select to Draw” box leads to another “Select to Draw” box, indicating further reaction or reduction using hydrogen gas (H₂) and palladium on carbon (Pd-C) as a catalyst.
Each step involves selecting and illustrating specific chemical structures and products, which would complete the reaction scheme.
### Explanation:
- **Met-OBn:** Likely refers to a methionine derivative with a protecting benzyl group.
- **DCC:** A coupling agent often used in peptide synthesis.
- **Piperidine:** A secondary amine commonly used to deprotect or transform compounds in organic synthesis.
- **H₂ and Pd-C:** Commonly used together for hydrogenation reactions, often reducing double bonds or removing protecting groups.
The diagram appears to illustrate a synthesis pathway, possibly involving peptide coupling or similar transformations, but requires additional input for a comprehensive understanding.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ffee5a196-0e10-4c2e-9c7f-7471e7c61611%2Fe30b67ac-749a-4cf9-9f5c-90e284c80a24%2Fgvhll7_processed.png&w=3840&q=75)
Transcribed Image Text:This diagram represents a chemical reaction scheme involving several steps and reagents.
1. **Top Right Reaction:**
- **Reagents:** Met-OBn and DCC
- An arrow is pointing from these reagents to a box labeled “Select to Draw,” indicating that a reaction occurs here, though the specific reaction or product is not shown.
2. **Middle Horizontal Reaction:**
- **Reagent:** Piperidine
- An arrow points from the right “Select to Draw” box to the left “Select to Draw” box, indicating a secondary reaction or transformation facilitated by piperidine.
3. **Bottom Vertical Reaction:**
- **Reagents:** H₂ and Pd-C
- An arrow pointing down from the left “Select to Draw” box leads to another “Select to Draw” box, indicating further reaction or reduction using hydrogen gas (H₂) and palladium on carbon (Pd-C) as a catalyst.
Each step involves selecting and illustrating specific chemical structures and products, which would complete the reaction scheme.
### Explanation:
- **Met-OBn:** Likely refers to a methionine derivative with a protecting benzyl group.
- **DCC:** A coupling agent often used in peptide synthesis.
- **Piperidine:** A secondary amine commonly used to deprotect or transform compounds in organic synthesis.
- **H₂ and Pd-C:** Commonly used together for hydrogenation reactions, often reducing double bonds or removing protecting groups.
The diagram appears to illustrate a synthesis pathway, possibly involving peptide coupling or similar transformations, but requires additional input for a comprehensive understanding.
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