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Draw structural formulas for all alkenes that could be used to prepare the alcohol shown below by oxymercuration.

**Chemical Reaction Explanation: Oxymercuration-Demercuration**

The image depicts a chemical reaction that involves the conversion of an alkene to an alcohol using the oxymercuration-demercuration method. This reaction is generally characterized by the addition of water across the carbon-carbon double bond in an alkene to form an alcohol.

**Reactants and Reagents:**

1. **Starting Material (Alkene):** The question mark in the image signifies the missing starting material, which is an alkene. Given the alcohol product, the alkene likely has a double bond where the hydroxyl group (OH) is added.

2. **Reagents:**
   - **Step 1:** Hg(OAc)₂ (Mercuric acetate) and H₂O (Water) are used to form a mercurinium ion intermediate.
   - **Step 2:** NaBH₄ (Sodium borohydride) is used to reduce the intermediate, replacing the mercury group with a hydrogen atom.

**Product:**

The product displayed is an alcohol: 
- It has a hydroxyl group (CHOH) attached to a secondary carbon.
- The structure includes a methyl group (CH₃) and a lengthy alkyl chain (CH₃CH₂CH₂CH=CHCH₂CH₂CH₃).

**Mechanism Overview:**

1. **Oxymercuration:** The alkene reacts with mercuric acetate in the presence of water to form a cyclic mercurinium ion. Water attacks the more substituted carbon, leading to the formation of an organomercury intermediate.

2. **Demercuration:** Sodium borohydride reduces the organomercury intermediate, leading to the replacement of the mercury portion with a hydrogen atom and resulting in the formation of the alcohol product.

This reaction is useful for its Markovnikov selectivity, adding the OH group to the more substituted carbon of the double bond, without rearrangements that can occur in typical acid-catalyzed hydration.
Transcribed Image Text:**Chemical Reaction Explanation: Oxymercuration-Demercuration** The image depicts a chemical reaction that involves the conversion of an alkene to an alcohol using the oxymercuration-demercuration method. This reaction is generally characterized by the addition of water across the carbon-carbon double bond in an alkene to form an alcohol. **Reactants and Reagents:** 1. **Starting Material (Alkene):** The question mark in the image signifies the missing starting material, which is an alkene. Given the alcohol product, the alkene likely has a double bond where the hydroxyl group (OH) is added. 2. **Reagents:** - **Step 1:** Hg(OAc)₂ (Mercuric acetate) and H₂O (Water) are used to form a mercurinium ion intermediate. - **Step 2:** NaBH₄ (Sodium borohydride) is used to reduce the intermediate, replacing the mercury group with a hydrogen atom. **Product:** The product displayed is an alcohol: - It has a hydroxyl group (CHOH) attached to a secondary carbon. - The structure includes a methyl group (CH₃) and a lengthy alkyl chain (CH₃CH₂CH₂CH=CHCH₂CH₂CH₃). **Mechanism Overview:** 1. **Oxymercuration:** The alkene reacts with mercuric acetate in the presence of water to form a cyclic mercurinium ion. Water attacks the more substituted carbon, leading to the formation of an organomercury intermediate. 2. **Demercuration:** Sodium borohydride reduces the organomercury intermediate, leading to the replacement of the mercury portion with a hydrogen atom and resulting in the formation of the alcohol product. This reaction is useful for its Markovnikov selectivity, adding the OH group to the more substituted carbon of the double bond, without rearrangements that can occur in typical acid-catalyzed hydration.
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