Propose an efficient synthesis for the following transformation: OH The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as “EBF"). If there is more than one correct solution, provide just one answer. A B 1) O3 1) ВНз-ТHF 2) H2O2, H2O 1) xs NaNH2 2) DMS 2) H2O D F dilute H2SO4 H2, Lindlar's catalyst Br2

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Chapter1: Chemical Foundations
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**Propose an efficient synthesis for the following transformation:**

A reaction is shown where a terminal alkyne is converted into a secondary alcohol.

**Instructions:**

The transformation above can be performed with some reagent or combination of the reagents listed below. Provide the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as “EBF”). If there is more than one correct solution, provide just one answer.

**Reagents:**

- **A**
  1) \( \text{O}_3 \)
  2) DMS

- **B**
  1) xs \( \text{NaNH}_2 \)
  2) \( \text{H}_2\text{O} \)

- **C**
  1) \( \text{BH}_3 \cdot \text{THF} \)
  2) \( \text{H}_2\text{O}_2, \text{H}_2\text{O} \)

- **D**
  Dilute \( \text{H}_2\text{SO}_4 \)

- **E**
  \( \text{H}_2 \), Lindlar's catalyst

- **F**
  \( \text{Br}_2 \)
Transcribed Image Text:**Propose an efficient synthesis for the following transformation:** A reaction is shown where a terminal alkyne is converted into a secondary alcohol. **Instructions:** The transformation above can be performed with some reagent or combination of the reagents listed below. Provide the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as “EBF”). If there is more than one correct solution, provide just one answer. **Reagents:** - **A** 1) \( \text{O}_3 \) 2) DMS - **B** 1) xs \( \text{NaNH}_2 \) 2) \( \text{H}_2\text{O} \) - **C** 1) \( \text{BH}_3 \cdot \text{THF} \) 2) \( \text{H}_2\text{O}_2, \text{H}_2\text{O} \) - **D** Dilute \( \text{H}_2\text{SO}_4 \) - **E** \( \text{H}_2 \), Lindlar's catalyst - **F** \( \text{Br}_2 \)
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