Propose an efficient synthesis for the following transformation: Br En 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 corre solution, provide just one answer. А В C Mel Br2 Na, NH3 (1) D E F Br2, H20 H2, Lindlar's catalyst NANH2 G H. NaBr, NaOH NaOH Br

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**Title: Efficient Synthesis in Organic Chemistry**

**Objective:**  
Propose an efficient synthesis for the following transformation, converting an alkyne to a specific product with a brominated carbon and an alcohol group via a sequence of chemical reactions.

**Transformation Overview:**
- Starting Material: Alkyne
- Products: A brominated alcohol with designated stereochemistry 

**Instructions:**  
The transformation can be performed with some reagent or combination from the list provided. Enter the necessary reagent(s) in the correct order as a single string of letters (e.g., “EBF”). Provide just one possible answer if multiple solutions exist.

**Reagents List:**

- **A:** MeI (Methyl Iodide)
- **B:** Br₂ (Bromine)
- **C:** Na, NH₃ (l) (Sodium in liquid Ammonia)
- **D:** Br₂, H₂O (Bromine in Water)
- **E:** H₂, Lindlar's catalyst 
- **F:** NaNH₂ (Sodium Amide)
- **G:** NaBr, NaOH (Sodium Bromide and Sodium Hydroxide)
- **H:** NaOH (Sodium Hydroxide)
- **I:** (CH₃CH₂)Br (Ethyl Bromide)

**Diagram Description:**
The diagram shows an alkyne undergoing transformation to a molecule with a brominated carbon and a hydroxyl group. It illustrates stereochemical details with specific orientation of substituents around the chiral centers. The reagents listed facilitate different reaction types such as reductions, additions, and substitutions necessary for achieving the desired product.
Transcribed Image Text:**Title: Efficient Synthesis in Organic Chemistry** **Objective:** Propose an efficient synthesis for the following transformation, converting an alkyne to a specific product with a brominated carbon and an alcohol group via a sequence of chemical reactions. **Transformation Overview:** - Starting Material: Alkyne - Products: A brominated alcohol with designated stereochemistry **Instructions:** The transformation can be performed with some reagent or combination from the list provided. Enter the necessary reagent(s) in the correct order as a single string of letters (e.g., “EBF”). Provide just one possible answer if multiple solutions exist. **Reagents List:** - **A:** MeI (Methyl Iodide) - **B:** Br₂ (Bromine) - **C:** Na, NH₃ (l) (Sodium in liquid Ammonia) - **D:** Br₂, H₂O (Bromine in Water) - **E:** H₂, Lindlar's catalyst - **F:** NaNH₂ (Sodium Amide) - **G:** NaBr, NaOH (Sodium Bromide and Sodium Hydroxide) - **H:** NaOH (Sodium Hydroxide) - **I:** (CH₃CH₂)Br (Ethyl Bromide) **Diagram Description:** The diagram shows an alkyne undergoing transformation to a molecule with a brominated carbon and a hydroxyl group. It illustrates stereochemical details with specific orientation of substituents around the chiral centers. The reagents listed facilitate different reaction types such as reductions, additions, and substitutions necessary for achieving the desired product.
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