For the reaction shown, which of the compounds below would be the expected enol intermediate? 1.9-BBN 2. H,O NaOH он OH он OH C O A OD

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**Chemical Reactions - Enol Intermediate Formation**

**Question:**
For the reaction shown, which of the compounds below would be the expected enol intermediate?

\[ \text{Reactant:} \]

*Structure of a molecule with a triple bond between the second and third carbon atom, starting from a terminal carbon with a single bond hydrogen.*

\[ \text{Reaction Conditions:} \]
1. 9-BBN
2. \( \text{H}_2\text{O}_2 / \text{NaOH} \)

**Possible Products:**
- **A.** Structure: A molecule with a two-carbon chain, with the first carbon bonded to a methyl group, a hydroxyl group (\( \text{OH} \)), and a hydrogen.
- **B.** Structure: A molecule with a three-carbon chain, with the first carbon bonded to a hydrogen and a hydroxyl group, and the second carbon bonded to a hydroxyl group.
- **C.** Structure: A molecule with a three-carbon chain, with the first carbon bonded to a methyl group, the second carbon bonded to hydrogen and a hydroxyl group, and the third carbon bonded to a hydroxyl group.
- **D.** Structure: A molecule with a two-carbon chain, with the first carbon bonded to a methyl group and the second carbon double-bonded to an oxygen atom.

**Answer Choices:**

- ○ A
- ○ C
- ○ D
- ○ B

**Explanation:**

In this reaction, we are conducting a hydroboration-oxidation of an alkyne. Typically, this process converts the terminal alkyne carbon into an enol, which can subsequently tautomerize to a ketone if applicable. In this problem, you need to determine the intermediate enol.

Consider the structures shown, specifically looking for the formation of the enol intermediate resulting from the specified reaction.

Please select the correct molecule from the choices provided.
Transcribed Image Text:**Chemical Reactions - Enol Intermediate Formation** **Question:** For the reaction shown, which of the compounds below would be the expected enol intermediate? \[ \text{Reactant:} \] *Structure of a molecule with a triple bond between the second and third carbon atom, starting from a terminal carbon with a single bond hydrogen.* \[ \text{Reaction Conditions:} \] 1. 9-BBN 2. \( \text{H}_2\text{O}_2 / \text{NaOH} \) **Possible Products:** - **A.** Structure: A molecule with a two-carbon chain, with the first carbon bonded to a methyl group, a hydroxyl group (\( \text{OH} \)), and a hydrogen. - **B.** Structure: A molecule with a three-carbon chain, with the first carbon bonded to a hydrogen and a hydroxyl group, and the second carbon bonded to a hydroxyl group. - **C.** Structure: A molecule with a three-carbon chain, with the first carbon bonded to a methyl group, the second carbon bonded to hydrogen and a hydroxyl group, and the third carbon bonded to a hydroxyl group. - **D.** Structure: A molecule with a two-carbon chain, with the first carbon bonded to a methyl group and the second carbon double-bonded to an oxygen atom. **Answer Choices:** - ○ A - ○ C - ○ D - ○ B **Explanation:** In this reaction, we are conducting a hydroboration-oxidation of an alkyne. Typically, this process converts the terminal alkyne carbon into an enol, which can subsequently tautomerize to a ketone if applicable. In this problem, you need to determine the intermediate enol. Consider the structures shown, specifically looking for the formation of the enol intermediate resulting from the specified reaction. Please select the correct molecule from the choices provided.
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