но A PBR3 HO Mg, Et20 B HO. trace acid H then H30* workup H3O E D

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Consider the following multistep synthesis. For each step, provide the missing organic structure.

### Transcription for Educational Website:

In this reaction sequence, a series of chemical transformations are illustrated:

1. **Starting Material and First Reaction:**
   - The starting compound is a phenol derivative with an acetyl group. The first reagent, \( \text{PBr}_3 \), is introduced. This leads to the formation of compound A, which appears to be an intermediate with a new functional group transformation likely occurring at the phenol site.

2. **Second Reaction:**
   - Compound A is then reacted with ethylene glycol (HO-CH2-CH2-OH) in the presence of a trace acid, resulting in compound B. This step typically protects the carbonyl group as an acetal.

3. **Third Reaction:**
   - The next step involves the use of magnesium (Mg) in diethyl ether (\( \text{Et}_2\text{O} \)), resulting in compound C. This is indicative of the formation of a Grignard reagent through the insertion of magnesium into the organic halide.

4. **Fourth Reaction:**
   - Compound C then reacts with formaldehyde (\( \text{H}_2\text{C=O} \)) followed by an acid workup (\( \text{H}_3\text{O}^+ \)), leading to compound D. This suggests the addition of the Grignard reagent to formaldehyde to form a primary alcohol.

5. **Final Reaction:**
   - Finally, compound D is treated with aqueous acid (\( \text{H}_3\text{O}^+ \)), leading to the final product, compound E. This step typically involves the removal of any protective groups or further rearrangements to yield the desired product.

### Diagram Explanation:

- **Structures and Arrows:** 
  - The diagram displays structural representations of organic molecules at each step with arrows indicating the direction of reactions. Each arrow transition marks a chemical reaction facilitated by the respective reagents.

- **Reagents and Conditions:**
  - Reagents and specific conditions (like trace acid or \( \text{H}_3\text{O}^+ \) workup) are specified alongside arrows to indicate their crucial role in driving each transformation.

This sequence exemplifies the strategic approach in organic synthesis where protective groups, Grignard reagents, and acid workups are used to achieve selective transformations and build complex structures from simpler starting materials.
Transcribed Image Text:### Transcription for Educational Website: In this reaction sequence, a series of chemical transformations are illustrated: 1. **Starting Material and First Reaction:** - The starting compound is a phenol derivative with an acetyl group. The first reagent, \( \text{PBr}_3 \), is introduced. This leads to the formation of compound A, which appears to be an intermediate with a new functional group transformation likely occurring at the phenol site. 2. **Second Reaction:** - Compound A is then reacted with ethylene glycol (HO-CH2-CH2-OH) in the presence of a trace acid, resulting in compound B. This step typically protects the carbonyl group as an acetal. 3. **Third Reaction:** - The next step involves the use of magnesium (Mg) in diethyl ether (\( \text{Et}_2\text{O} \)), resulting in compound C. This is indicative of the formation of a Grignard reagent through the insertion of magnesium into the organic halide. 4. **Fourth Reaction:** - Compound C then reacts with formaldehyde (\( \text{H}_2\text{C=O} \)) followed by an acid workup (\( \text{H}_3\text{O}^+ \)), leading to compound D. This suggests the addition of the Grignard reagent to formaldehyde to form a primary alcohol. 5. **Final Reaction:** - Finally, compound D is treated with aqueous acid (\( \text{H}_3\text{O}^+ \)), leading to the final product, compound E. This step typically involves the removal of any protective groups or further rearrangements to yield the desired product. ### Diagram Explanation: - **Structures and Arrows:** - The diagram displays structural representations of organic molecules at each step with arrows indicating the direction of reactions. Each arrow transition marks a chemical reaction facilitated by the respective reagents. - **Reagents and Conditions:** - Reagents and specific conditions (like trace acid or \( \text{H}_3\text{O}^+ \) workup) are specified alongside arrows to indicate their crucial role in driving each transformation. This sequence exemplifies the strategic approach in organic synthesis where protective groups, Grignard reagents, and acid workups are used to achieve selective transformations and build complex structures from simpler starting materials.
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