Consider the following alcohol, A. When reacted with one (or a combination of two) reagents in the "reagent box," A can be transformed into a variety of different molecules. H HO NaH: DMF POCI3 excess Nal DMSO SOBr₂ .Н PCI HO HO A Reagent Box 11 cat. H₂SO4 H₂O: acetone to PBr3 POBr3 List a reagent (or combination of two) from the reaction box capable of transforming A into the products given below. Note: there are many possible answers! Br excess SOCI₂ TSCI НО 18 CI OH

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### Chemical Transformation of Alcohol A

**Overview:**
Consider the following alcohol, A. When reacted with one (or a combination of two) reagents in the "reagent box," A can be transformed into a variety of different molecules.

**Structure of Alcohol A:**
- Chemical formula: HO—(CH₂)₄—OH

**Reagent Box:**
The reagent box contains the following reagents:
- NaH, DMF
- NaI, DMSO
- \( \text{SOBr}_2 \)
- \( \text{POCl}_3 \) (with pyridine)
- \( \text{PCl}_5 \)
- \( \text{PBr}_3 \)
- \( \text{POBr}_3 \) (excess, with pyridine)
- \( \text{SOCl}_2 \)
- TsCl (with pyridine)
- \( \text{Cl—} \text{C} \stackrel{||}{\text{O}} \text{C—} \text{O} \stackrel{||}{\text{O}} \text{C—} \text{Cl} \) (with benzene, excess)
- \( \text{cat. } \text{H}_2\text{SO}_4 \), \( \text{H}_2\text{O}_2 \), acetone

**Products and Reagents:**
List a reagent (or combination of two) from the reaction box capable of transforming \( A \) into the products given below. Note: there are many possible answers!

**Possible Products:**
1. **HO—(CH₂)₄—I:** An alcohol-to-iodine transformation.
2. **HO—(CH₂)₄—Br:** An alcohol-to-bromine transformation.
3. **Cl—(CH₂)₄—Cl:** An alcohol-to-chlorine transformation on both ends.
4. **\( \text{O} \stackrel{||}{\text{C}} \text{(CH₂)₃} \text{C} \stackrel{||}{\text{O}} \text{H} \):** A dicarboxylic acid derivative.
5. **\( \text{C} \stackrel{||}{\text{C}} \text{(CH₂)₂}
Transcribed Image Text:### Chemical Transformation of Alcohol A **Overview:** Consider the following alcohol, A. When reacted with one (or a combination of two) reagents in the "reagent box," A can be transformed into a variety of different molecules. **Structure of Alcohol A:** - Chemical formula: HO—(CH₂)₄—OH **Reagent Box:** The reagent box contains the following reagents: - NaH, DMF - NaI, DMSO - \( \text{SOBr}_2 \) - \( \text{POCl}_3 \) (with pyridine) - \( \text{PCl}_5 \) - \( \text{PBr}_3 \) - \( \text{POBr}_3 \) (excess, with pyridine) - \( \text{SOCl}_2 \) - TsCl (with pyridine) - \( \text{Cl—} \text{C} \stackrel{||}{\text{O}} \text{C—} \text{O} \stackrel{||}{\text{O}} \text{C—} \text{Cl} \) (with benzene, excess) - \( \text{cat. } \text{H}_2\text{SO}_4 \), \( \text{H}_2\text{O}_2 \), acetone **Products and Reagents:** List a reagent (or combination of two) from the reaction box capable of transforming \( A \) into the products given below. Note: there are many possible answers! **Possible Products:** 1. **HO—(CH₂)₄—I:** An alcohol-to-iodine transformation. 2. **HO—(CH₂)₄—Br:** An alcohol-to-bromine transformation. 3. **Cl—(CH₂)₄—Cl:** An alcohol-to-chlorine transformation on both ends. 4. **\( \text{O} \stackrel{||}{\text{C}} \text{(CH₂)₃} \text{C} \stackrel{||}{\text{O}} \text{H} \):** A dicarboxylic acid derivative. 5. **\( \text{C} \stackrel{||}{\text{C}} \text{(CH₂)₂}
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