Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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### Question: Which is the best method for the following transformation? ### Diagram: The diagram depicts a chemical reaction where an alkene is converted to an alcohol. The structure on the left is an alkene with a double bond between two carbon atoms (one of which is a methane group), and the structure on the right is an alcohol where the OH group is attached to what was the formerly double-bonded carbon. ``` H3C-CH=CH2 → H3C-CH(OH)-CH3 ``` ### Options: A. 1. BH₃, THF 2. H₂O₂, OH⁻ B. H⁺, H₂O C. Concentrated H₂SO₄ D. 1. Hg(OAc)₂, H₂O 2. NaBH₄ ## Explanation: ### Option A: The combination of BH₃ (borane) in THF (tetrahydrofuran) followed by H₂O₂ (hydrogen peroxide) and OH⁻ (hydroxide ion) is usually indicative of hydroboration-oxidation. This method results in the anti-Markovnikov addition of water (OH and H), where the hydroxyl group attaches to the less substituted carbon atom. ### Option B: Using H⁺ (proton, typically in the form of an acid) and H₂O (water) usually leads to the Markovnikov addition of water to the double bond, where the hydroxyl group attaches to the more substituted carbon atom. ### Option C: Concentrated H₂SO₄ (sulfuric acid) can be used for acid-catalyzed hydration of alkenes, which typically follows Markovnikov's rule. ### Option D: The use of Hg(OAc)₂, H₂O followed by NaBH₄ (sodium borohydride) describes an oxymercuration-demercuration reaction. This method also results in Markovnikov addition of water without rearrangements. --- ### Conclusion: For converting an alkene to an alcohol with the anti-Markovnikov orientation, the best method is **Option A** (1. BH₃, THF 2. H₂O₂, OH⁻).
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Transcribed Image Text:### Question: Which is the best method for the following transformation? ### Diagram: The diagram depicts a chemical reaction where an alkene is converted to an alcohol. The structure on the left is an alkene with a double bond between two carbon atoms (one of which is a methane group), and the structure on the right is an alcohol where the OH group is attached to what was the formerly double-bonded carbon. ``` H3C-CH=CH2 → H3C-CH(OH)-CH3 ``` ### Options: A. 1. BH₃, THF 2. H₂O₂, OH⁻ B. H⁺, H₂O C. Concentrated H₂SO₄ D. 1. Hg(OAc)₂, H₂O 2. NaBH₄ ## Explanation: ### Option A: The combination of BH₃ (borane) in THF (tetrahydrofuran) followed by H₂O₂ (hydrogen peroxide) and OH⁻ (hydroxide ion) is usually indicative of hydroboration-oxidation. This method results in the anti-Markovnikov addition of water (OH and H), where the hydroxyl group attaches to the less substituted carbon atom. ### Option B: Using H⁺ (proton, typically in the form of an acid) and H₂O (water) usually leads to the Markovnikov addition of water to the double bond, where the hydroxyl group attaches to the more substituted carbon atom. ### Option C: Concentrated H₂SO₄ (sulfuric acid) can be used for acid-catalyzed hydration of alkenes, which typically follows Markovnikov's rule. ### Option D: The use of Hg(OAc)₂, H₂O followed by NaBH₄ (sodium borohydride) describes an oxymercuration-demercuration reaction. This method also results in Markovnikov addition of water without rearrangements. --- ### Conclusion: For converting an alkene to an alcohol with the anti-Markovnikov orientation, the best method is **Option A** (1. BH₃, THF 2. H₂O₂, OH⁻).
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