6. Both acid-catalyzed hydration and oxymercuration-demercuration are addition reactions that add a hydroxyl group (--OH) and a hydrogen atom across a t-bond to make a Markovnikov product. Because of this, both reactions can often end with the same major organic product. Explain in 1-3 complete sentences why substrate A leads to the same product no matter the conditions and why substrate B leads to two different products based on reaction conditions. H₂SO OH

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**Explanation of Acid-Catalyzed Hydration and Oxymercuration-Demercuration**

Both acid-catalyzed hydration and oxymercuration-demercuration are addition reactions that add a hydroxyl group (-OH) and a hydrogen atom across a π-bond to create a Markovnikov product. Consequently, these reactions frequently result in the same major organic product.

**Task**: Explain in 1–3 complete sentences why substrate A leads to the same product no matter the conditions and why substrate B leads to two different products based on reaction conditions.

**Chemical Reactions Illustrated:**

- **Substrate A:**
  - Reaction 1: With H₂SO₄ and H₂O, substrate A produces an alcohol, with the hydroxyl group added according to Markovnikov’s rule, in a racemic mixture.
  - Reaction 2: With 1. Hg(OAc)₂ and 2. NaBH₄, substrate A again produces a racemic mixture of the alcohol, showing the same product as Reaction 1.

- **Substrate B:**
  - Reaction 1: With H₂SO₄ and H₂O, substrate B yields a racemic mixture of the product with Markovnikov addition of the hydroxyl group.
  - Reaction 2: With 1. Hg(OAc)₂ and 2. NaBH₄, substrate B also results in the formation of a racemic mixture of the product through a Markovnikov addition mechanism.

**Analysis:**
Substrate A, being a linear alkene, consistently produces the same major product under both acid-catalyzed hydration and oxymercuration-demercuration due to its symmetrical structure. On the other hand, substrate B, a cyclic alkene, can have different reaction pathways leading to distinct stereochemical outcomes depending on the conditions. This results in the potential for two differing products in certain scenarios.
Transcribed Image Text:**Explanation of Acid-Catalyzed Hydration and Oxymercuration-Demercuration** Both acid-catalyzed hydration and oxymercuration-demercuration are addition reactions that add a hydroxyl group (-OH) and a hydrogen atom across a π-bond to create a Markovnikov product. Consequently, these reactions frequently result in the same major organic product. **Task**: Explain in 1–3 complete sentences why substrate A leads to the same product no matter the conditions and why substrate B leads to two different products based on reaction conditions. **Chemical Reactions Illustrated:** - **Substrate A:** - Reaction 1: With H₂SO₄ and H₂O, substrate A produces an alcohol, with the hydroxyl group added according to Markovnikov’s rule, in a racemic mixture. - Reaction 2: With 1. Hg(OAc)₂ and 2. NaBH₄, substrate A again produces a racemic mixture of the alcohol, showing the same product as Reaction 1. - **Substrate B:** - Reaction 1: With H₂SO₄ and H₂O, substrate B yields a racemic mixture of the product with Markovnikov addition of the hydroxyl group. - Reaction 2: With 1. Hg(OAc)₂ and 2. NaBH₄, substrate B also results in the formation of a racemic mixture of the product through a Markovnikov addition mechanism. **Analysis:** Substrate A, being a linear alkene, consistently produces the same major product under both acid-catalyzed hydration and oxymercuration-demercuration due to its symmetrical structure. On the other hand, substrate B, a cyclic alkene, can have different reaction pathways leading to distinct stereochemical outcomes depending on the conditions. This results in the potential for two differing products in certain scenarios.
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